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Product Details of [ 6500-65-8 ]

CAS No. :6500-65-8 MDL No. :MFCD07369971
Formula : C12H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WLRMIOGKWITDNU-UHFFFAOYSA-N
M.W : 190.24 Pubchem ID :266815
Synonyms :

Calculated chemistry of [ 6500-65-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.59
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 2.54
Log Po/w (WLOGP) : 2.6
Log Po/w (MLOGP) : 1.92
Log Po/w (SILICOS-IT) : 3.24
Consensus Log Po/w : 2.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.256 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (Ali) : -2.74
Solubility : 0.347 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.8
Solubility : 0.0299 mg/ml ; 0.000157 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 6500-65-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6500-65-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6500-65-8 ]

[ 6500-65-8 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 6500-65-8 ]
  • [ 36112-54-6 ]
YieldReaction ConditionsOperation in experiment
98% With sodium tetrahydroborate In methanol; water at 0℃;
96% With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 16h; Heating;
With lithium aluminium tetrahydride In diethyl ether
With 4-aza-N-benzyl-bicyclo<2,2,2>octyl ammonium borohydride In <i>tert</i>-butyl alcohol for 76h; Yield given;

  • 2
  • [ 6500-65-8 ]
  • [ 71735-06-3 ]
YieldReaction ConditionsOperation in experiment
With sodium amide In diethyl ether; ethanol
  • 3
  • [ 50683-13-1 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
With copper diacetate; zinc In acetic acid
  • 4
  • [ 6500-64-7 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
100% With PPA; In chlorobenzene; at 80℃; for 15h; The solution of PPA in chlorobenzene was added Int-20e (4 g) at 80 C and the mixture was allowed to stir at 80 C for about 15 hours. The solution was removed and the residue was dissolved in ethyl acetate and washed with NaOH (IN, aqueous) fllowed by brine. The organic layer was dried over Na2SC>4s filtered and concentrated in vacuo to provide Compound Int-20f (3.8 g, 100 %).
82% With PPA; at 100℃; for 2h; To <strong>[6500-64-7]5-(3-methoxyphenyl)pentanoic acid</strong> 1f-2 (4 g,19.23 mmol) was added PPA (20 g). The reaction mixture was heated at 100C for 2h. It was cooled to RT and poured into ice-cold water then extracted with Teac (2 x 500 ml). The combined organic layers were washed with a saturated sodium carbonate solution (500 ml) then brine (200 ml). It was dried over sodium sulphate and concentrated down. The crude compound was purified by column chromatography (silica gel 100-200 mesh) using 0-10% EtOAc in petroleum ether to give the title compound 1f-3 as a pale brown solid (3 g,82% yield). LCMS [M+H]+ 191.
80% <strong>[6500-64-7]5-(3-methoxyphenyl)pentanoic acid</strong> (81.5 kg, 1.0 eq) was dissolved in dichloromethane (540.0 kg) and 1.8 kg of dimethylformamide was added.Under nitrogen protection, the temperature of the system was reduced to -5C, and oxalyl chloride (74.9 kg, 1.5 eq) was slowly added dropwise. After the addition was completed, the reaction was performed for 2 hours, and anhydrous aluminum trichloride (52.3 kg, 1.0 eq) was added in portions.),After 6 hours of reaction, the controlled reaction was completed. Water was added to the system to quench the reaction. The organic phase was separated. The organic phase was washed with 3N hydrochloric acid, 10% sodium hydroxide, and saturated brine in that order. The pad was filtered with a pad of silica gel.When concentrated to 60-80 L, the concentration was stopped and petroleum ether (120.0 kg) was added to pulp to give 2-methoxy-6,7,8,9-tetrahydrobenzocycloheptan-5-one (59.5 kg).Yield: 80%. The results of the nuclear magnetic test are shown in Fig. 1, and the results of the mass spectrometry test are shown in Fig. 2.
76% With methanesulfonic acid; phosphorus pentoxide; for 12h;Inert atmosphere; 48. 2-Methoxy-6,7,8,9-tetrahydro-5H-cyclobenzoheptan-5-one (48) To pentanoic acid 47 (3.01 g, 14.5 mmol) in a flask, 40 g/mL of Eatons reagent (from Acros) was added and the solution was stirred for 12 h. The reaction mixture was poured over ice and the ice was allowed to melt. The aqueous phase was extracted with CH2Cl2 (3*100 mL) and NaHCO3 powder was added in small amounts until the pH was neutral. The organic phase was treated with brine, dried over Na2SO4, filtered and solvent evaporated under reduced pressure to obtain 48 as a white solid. Flash chromatography of the crude using a prepacked 50 g silica column, Eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 10% A/90% B over 3.18 min (1 CV), 10% A/90% B?60% A/40% B over 33.0 min (10 CV), 60% A/40% B over 6.36 min (2 CV); flow rate 40.0 mL/min; monitored at lambdalambda254 and 280 nm afforded 48, (2.10 g, 11.0 mmol, 76% yield) as a white solid. 1H NMR (CDCl3, 500 MHz): delta 7.78 (1H, d, J=8.6 Hz, H-4'), 6.81 (1H, dd, J=8.6, 2.5 Hz, H-3'), 6.70 (1H, d, J=2.5 Hz, H-4'), 3.85 (3H, s, OCH3-2), 2.91 (2H, m, H-9), 2.71 (2H, m, CH3-6), 1.89 (2H, m, H-8), 1.81 (2H, m, H-7). 13C NMR (CDCl3, 500 MHz): delta 204.3 (C, C-5), 162.7 (C, C-2), 144.2 (C, C-1a), 131.6 (C, C-4-a), 131.3 (C, C-4), 114.9 (C, C-1), 111.7 (C, C-3), 55.3 (CH3, OCH3-2), 40.7 (CH2, C-6), 32.9 (CH2, C-9), 25.1 (CH2, C-8), 20.7 (CH2, C-7).
70% With methanesulfonic acid; phosphorus pentoxide; at 20℃; for 12h;Inert atmosphere; 4.1.1.45 2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (14) To carboxylic acid 8 (4.43 g, 21.3 mmol) was added Eaton's reagent (43 mL, 3 g per mmol of compound 8), and the mixture was stirred at room temperature for 12 h. The mixture was then poured over ice and neutralized with sodium bicarbonate. The aqueous layer was extracted with EtOAc (3 * 50 mL). The combined organic phase was dried over sodium sulfate, evaporated under reduced pressure, and purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7% A/93% B (1 CV), 7% A/93% B ? 30% A/70% B (10 CV), 30% A/70% B (2 CV); flow rate: 50 mL/min; monitored at 254 and 280 nm] to afford benzosuberone 14 (2.80 g, 14.7 mmol, 70%) as a white solid. 1H NMR (500 MHz, CDCl3) delta 7.59 (1H, d, J = 8.5 Hz), 6.61 (1H, dd, J = 8.5, 2.5 Hz), 6.51 (1H, d, J = 2.5 Hz), 3.63 (3H, s), 2.70 (2H, t, J = 6 Hz), 2.51 (2H, t, J = 6 Hz), 1.67 (2H, p, J = 7.5 Hz), 1.59 (2H, p, J = 5.5 Hz). 13C NMR (125 MHz, CDCl3) delta 203.5, 162.5, 144.1, 131.3, 131.0, 114.7, 111.6, 55.1, 40.5, 32.6, 24.9, 20.5.

  • 5
  • [ 26473-47-2 ]
  • [ 6500-65-8 ]
  • [ 153265-22-6 ]
YieldReaction ConditionsOperation in experiment
79% In benzene for 12h; Heating;
  • 6
  • [ 6500-65-8 ]
  • [ 72472-43-6 ]
YieldReaction ConditionsOperation in experiment
100% With bromine In diethyl ether at 0 - 30℃; for 2h;
98.5% With copper(ll) bromide In chloroform; ethyl acetate at 75℃; for 1h; 1 6-BROMO-2-METHOXY-6,7,8,9-TETRAHYDRO-BENZOCYCLOHEPTEN-5-ONE (4) 2-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one 2 (0.5 g, 2.62 mmol) was taken into 1:1 mixture of ethyl acetate and chloroform (10 mL), then CuBr2 (1.17 g, 5.26 mmol) was added and the reaction was heated at 75° C. for 1 hour. The reaction was filtered and concentrated. The resulting material was taken into Et2O and washed with water (2*), saturated NaHCO3 (2*) and brine (1*). The ether layer was dried over MgSO4, filtered and concentrated to yield 0.139 g (98.5%) of product 4 as a viscous liquid. 1H NMR (CDCl3) δ 7.69 (d, 1H, J=8.6 Hz), 6.81 (dd, 1H, J=8.6 Hz, 2.3 Hz), 6.71 (br s, 1H), 4.88 (dd, 1H, J=7.9 Hz, 4.2 Hz), 3.85 (s, 3H), 3.04 (m, 1H), 2.91 (m, 1H), 2.32 (m, 2H), 2.01 (m, 2H).
95% With bromine In diethyl ether for 2h;
75% With bromine In diethyl ether at 0℃; for 1h; Intermediate (Iv1 ). 6-bromo-2-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one To a solution of 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one (10 g, 50.99 mmol) in diethyl ether (100 ml), was added dropwise at 0°C a solution of bromine (2.80 ml, 54.05). The reaction mixture was stirred for 1 hour at 0°C then EtOAc and water were added. The organic phase was dried over magnesium sulfate, filtered, evaporated under reduced pressure to give a residue which was purified by flash chromatography eluting with with a gradient of EtOAc in heptane (0 to 10% ; V/V) to give 10.29 g (75%) of 6-bromo-2-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5- one (Iv1 ). LC/MS (m/z, MH+): 269
75% With bromine In diethyl ether at 0℃; for 1h; Inert atmosphere; Intermediate (Iv). 6-bromo-2-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one To a solution of 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one (10 g, 50.99 mmol) in diethyl ether (100 ml), was added dropwise at 0° C. a solution of bromine (2.80 ml, 54.05). The reaction mixture was stirred for 1 hour at 0° C. then EtOAc and water were added. The organic phase was dried over magnesium sulfate, filtered, evaporated under reduced pressure to give a residue which was purified by flash chromatography eluting with a gradient of EtOAc in heptane (0 to 10%; V/V) to give 10.29 g (75%) of 6-bromo-2-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (lv). LC/MS (m/z, MH+): 269
60% With bromine In diethyl ether for 2h; 20.E Int-20f (3.8 g) was dissolved in ethyl ether and treated with a drop wise addition of Br2 (3.2 g). The solution was allowed to stir for two additional hours and then worked up by washed a 10% Na2SC>3 solution, NaHC03 and brine. The organic layer was dried over Na2S04, filtered and concentrated in vacuo to provide Compound Int-20g (4.0 g, 60 %). -N R: (CDC13) δ: 7.71 (d, J= 8 Hz, 1 H), 7.83 (d, J= 8 Hz, 1 H), 6.73 (s, 1 H), 4.92 - 4.89 (m, 1 H), 3.87 (s, 3 H), 3.07 - 3.03 (m, 1 H); 2.94 - 2.88 (m, 1 H), 2.40 - 2.28 (m, 2 H), 2.07 - 2.02 (ra, 2 H).

  • 7
  • [ 6500-65-8 ]
  • 9-methoxy-cis-bicyclo<5.4.0>undecan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen at 80℃;
  • 9
  • [ 72472-43-6 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
95 % Spectr. With sulfuric acid; sodium iodide In tetrahydrofuran; water for 24h; Ambient temperature;
Multi-step reaction with 2 steps 1: 93 percent / NaBH4 2: aq.NaOH / tetrahydrofuran / 22 h / Heating
  • 10
  • [ 105902-60-1 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
80% With barium permanganate In acetonitrile for 5h; Heating;
70% With <(Py)2Ag>2Cr2O7 In benzene for 11h; Heating;
  • 11
  • [ 132555-99-8 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
80% With barium permanganate In acetonitrile for 2h; Heating;
80% With polymeric complex of oxodiperoxochromium(VI) compound and pyrazine (Pyz-CrO5)n In dichloromethane for 0.5h; Ambient temperature;
  • 12
  • [ 6500-65-8 ]
  • [ 100-52-7 ]
  • [ 77607-57-9 ]
YieldReaction ConditionsOperation in experiment
77% With potassium hydroxide In methanol 1.) 10 deg C, 30 min, 2.) room temperature, 4 h;
  • 13
  • [ 6500-65-8 ]
  • [ 64-19-7 ]
  • [ 78431-49-9 ]
YieldReaction ConditionsOperation in experiment
77% With hydrazine hydrate Heating;
  • 14
  • [ 111171-81-4 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
59% With silver trifluoromethanesulfonate In dichloromethane for 17h; Ambient temperature;
  • 15
  • [ 6500-65-8 ]
  • [ 33513-42-7 ]
  • [ 74234-62-1 ]
YieldReaction ConditionsOperation in experiment
80% With trichlorophosphate for 5h;
  • 16
  • [ 89414-39-1 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
51% With titanium tetrachloride for 18h; 1.) -78 degC, 2.) -10 to 0 degC;
  • 17
  • [ 6500-66-9 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
47% With barium permanganate In acetonitrile for 2h; Heating;
  • 18
  • [ 6500-65-8 ]
  • [ 3470-51-7 ]
YieldReaction ConditionsOperation in experiment
100% With aluminum (III) chloride In toluene Reflux;
100% With aluminum (III) chloride In toluene at 91℃; for 0.75h; Intermediate (A2). 2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one To a solution of 2-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (15 g, 78.85 mmol) in toluene (400 ml) was added AlCl3 (25 g, 187.49 mmol). The reaction mixture was stirred at 91° C. (bath temperature) for 45 minutes, cooled to room temperature and poured onto ice (900 g). The slurry was stirred for 20 minutes and the solid formed was filtered, washed with water (200 ml), and diisopropyl ether (200 ml), and then was dried to give 14.1 g (100%) of 2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (A2) as a beige powder. (0439) 1H NMR (400 MHz, DMSO-d6, δ ppm): 10.1 (s, 1H); 7.53 (d, 1H); 6.68 (dd, 1H); 6.62 (d, 1H); 2.84 (t, 2H); 2.52 (t, 2H); 1.65 (q, 2H); 1.55 (q, 2H). (0440) LC/MS (m/z, MH+): 177
80% With trimethylammonium heptachlorodialuminate at 80℃; for 1h; Microwave irradiation; Inert atmosphere; 46 4.1.1.46. 2-Hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (39) 4.1.1.46 2-Hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (39)31,55 To benzosuberone 14 (0.89 g, 4.7 mmol) in a 20 mL microwave vial was added [TMAH][Al2Cl7] (22 mL, 0.53 M), and the reaction mixture was subjected to microwave irradiation for 1 h at 80 °C. The reaction mixture was poured into water (50 mL) and extracted with EtOAc (3 * 25 mL). The combined organic phase was dried over sodium sulfate and evaporated under reduced pressure. The crude reaction product was purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7%/93% B (1 CV), 7% A/93% B → 60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 50 mL/min; monitored at 254 and 280 nm] to afford alcohol 39 (0.66 g, 3.8 mmol, 80%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.73 (1H, d, J = 8.5 Hz), 6.75 (1H, dd, J = 8.5, 2.5 Hz), 6.67 (1H, d, J = 2 Hz), 3.84 (1H, s), 2.87 (2H, t, J = 6 Hz), 2.71 (2H, t, J = 6 Hz), 1.82 (4H, m).
65% With chloro-trimethyl-silane; sodium iodide In acetonitrile at 80 - 90℃; for 24h; Sealed tube; C 2-Hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (1f-4): A stirred solution of 2-methoxy-6,7,8,9-tetrahydro-5/-/-benzo[7]annulen-5-one 1f-3 (3 g,15.78 mmol) in CH3CN (30 ml) was treated with Nal (14.2 g,94.79 mmol) followed by TMS-CI (12.1 ml,94.79 mmol) at rt then heated at 80-90°C for 24h in a sealed tube. The reaction mixture was poured into water (100 ml) and extracted with EtOAc (2 x 200ml). The organic layer was concentrated down. The crude product was purified by column chromatography (silica gel 100-200 mesh) using 0-50% EtOAc in petroleum ether to give the title compound 1f-4 as a pale brown solid (1.8 g,65% yield). LCMS [M+H]+ 177.
With aluminum tri-bromide In benzene
With aluminium trichloride
With aluminum (III) chloride In toluene Reflux;
Stage #1: 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one With trimethylammonium heptachlorodialuminate at 80℃; for 1h; Sealed tube; Microwave irradiation; Inert atmosphere; Stage #2: With water A.51 51. 2-Hydroxy-6,7,8,9-tetrahydro-5H-cyclobenzoheptan-5-one (51) 2-Methoxy-6,7,8,9-tetrahydro-5H-cyclobenzoheptan-5-one (48) (0.505 g, 2.66 mmol) was added to 5 mL microwave vial with stir bar. To the vial was added [TMAH][Al2Cl7] solution (5.65 mL, 0.9423 M, 5.32 mmol). The vial was sealed and placed in a microwave reaction chamber for 1 h at 80° C. with 30 sec of pre-stirring. The reaction mixture was then slowly added to H2O (20 mL). The aqueous reaction mixture was extracted with EtOAc (4*25 mL). The combined organic layers were washed with brine, dried with Na2SO4, evaporated under reduced pressure and purified by flash chromatography with a prepacked 50 g silica gel column [eluents; solvent A, EtOAc, solvent B, hexanes; gradient; 5% A/95% B→7% A/93% B (1 CV), 7% A/93% B→60% A/40% B (12 CV), 60% A/40% B (5.5 CV); flow rate 40 mL/min; monitored at λλ254 and 280 nm]. Alcohol analog 51 (0.407 g, 2.31 mmol, 87% yield) was obtained as a light pink solid, Rf=0.24 (70:30 Hexanes:EtOAc). 1H NMR (DMSO, 500 MHz): δ 10.10 (1H, s, H=Ar-OH), 7.54 (1H, d, J=8.6 Hz, H=Ar-H), 6.68 (1H, dd, J=8.6, 2.2 Hz, H=Ar-H), 6.63 (1H, d, J=2.2 Hz, H=Ar-H), 2.83 (2H, t, J=6.2 Hz, H=CH2), 2.61 (2H, t, J=6.0 Hz, H=CH2), 1.75 (2H, p, J=6.5 Hz, H=CH2), 1.66 (2H, p, J=6.2 Hz, H=CH2). 13C NMR (DMSO, 125 MHz): δ 203.0, 161.6, 145.0, 131.3, 130.0, 116.6, 113.9, 40.6, 32.3, 25.0, 20.6.
With aluminum (III) chloride In benzene Reflux;

Reference: [1]Maximov, Philipp Y.; Fernandes, Daphne J.; McDaniel, Russell E.; Myers, Cynthia B.; Curpan, Ramona F.; Jordan, V. Craig [Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4569 - 4583]
[2]Current Patent Assignee: SANOFI - US9714221, 2017, B1 Location in patent: Page/Page column 197
[3]Herdman, Christine A.; Devkota, Laxman; Lin, Chen-Ming; Niu, Haichan; Strecker, Tracy E.; Lopez, Ramona; Liu, Li; George, Clinton S.; Tanpure, Rajendra P.; Hamel, Ernest; Chaplin, David J.; Mason, Ralph P.; Trawick, Mary Lynn; Pinney, Kevin G. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7497 - 7520]
[4]Current Patent Assignee: ONTARIO INSTITUTE FOR CANCER RESEARCH - WO2019/109188, 2019, A1 Location in patent: Paragraph 00240
[5]Khan,A.M. et al. [Journal of the Chemical Society C: Organic, 1966, p. 990 - 994]
[6]Lal; Khanna; Anand [Journal of medicinal chemistry, 1972, vol. 15, # 1, p. 23 - 27]
[7]Location in patent: scheme or table Negoro, Nobuyuki; Sasaki, Shinobu; Ito, Masahiro; Kitamura, Shuji; Tsujihata, Yoshiyuki; Ito, Ryo; Suzuki, Masami; Takeuchi, Koji; Suzuki, Nobuhiro; Miyazaki, Junichi; Santou, Takashi; Odani, Tomoyuki; Kanzaki, Naoyuki; Funami, Miyuki; Tanaka, Toshimasa; Yasuma, Tsuneo; Momose, Yu [Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1538 - 1552]
[8]Current Patent Assignee: BAYLOR UNIVERSITY - US2012/130129, 2012, A1 Location in patent: Page/Page column 17
[9]Kammath, Viju Balachandran; Šolomek, Tomáš; Ngoy, Bokolombe Pitchou; Heger, Dominik; Klán, Petr; Rubina, Marina; Givens, Richard S. [Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1718 - 1729]
  • 19
  • trans-5,6-dibromo-2-methoxy-5,6,7,8,9,10-hexahydrobenzocyclooctene [ No CAS ]
  • [ 6500-65-8 ]
  • [ 120316-33-8 ]
  • 2-Methoxy-8,9-dihydro-7H-benzocycloheptene-5-carbaldehyde [ No CAS ]
  • [ 120316-30-5 ]
YieldReaction ConditionsOperation in experiment
80% With water; magnesium carbonate In 1,4-dioxane for 22h; Heating; Yields of byproduct given;
With water; magnesium carbonate In 1,4-dioxane for 22h; Heating; Yields of byproduct given. Title compound not separated from byproducts;
  • 20
  • [ 6500-65-8 ]
  • [ 1885-29-6 ]
  • 3-Methoxy-6,7-dihydro-5H-13-aza-benzo[3,4]cyclohepta[1,2-b]naphthalen-8-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate In toluene for 24h; Heating;
  • 21
  • [ 110-52-1 ]
  • [ 6500-65-8 ]
  • [ 244084-59-1 ]
YieldReaction ConditionsOperation in experiment
78% With potassium <i>tert</i>-butylate In benzene for 2.5h; Heating;
  • 22
  • [ 6500-65-8 ]
  • [ 23908-30-7 ]
YieldReaction ConditionsOperation in experiment
73% With sodium methylate; isopentyl nitrite In methanol at 20℃; for 48h; 1 Into the solution of NaOMe (810 mg, 15 mmol) in 50 mL of MeOH was added 7-methoxybenzosuberone (1.90 g, 10 mmol) and isopentyl nitrite (1.48 mL, 11 mmol). The mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated under reduced pressure. The residue was taken up in methylene chloride, washed with H2O. The aqueous layer was neutralized with IN aqueous HCl and extracted with methylene chloride. The combined organic phases were dried (Na2SO4), filtered and concentrated. The residue was recrystallized from CH2Cl2/hexanes to give 29a (1.6 g, 73%) as a white solid. MS (ESI) [M+H+]: 220.
  • 23
  • [ 6500-65-8 ]
  • C17H20O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 78 percent / t-BuOK / benzene / 2.5 h / Heating 2: 80 percent / n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 - -25 °C 3: 93 percent / N-chlorosuccinimide / CH2Cl2; H2O / 2 h
  • 24
  • [ 6500-65-8 ]
  • [ 244084-68-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 78 percent / t-BuOK / benzene / 2.5 h / Heating 2: 80 percent / n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 - -25 °C
  • 25
  • [ 6500-65-8 ]
  • [ 153265-04-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C
Multi-step reaction with 8 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating
Multi-step reaction with 8 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating
Multi-step reaction with 7 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating

  • 26
  • [ 6500-65-8 ]
  • B-homo-3-methoxy-11-thia-15-azoestra-1,3,5(10),8,14-pentaene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 7: 62 percent / aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 7 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: NaN3 / H2O 7: 62 percent / aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 13 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 13: 62 percent / aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 13 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: NaN3 / H2O 13: 62 percent / aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 13 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 13: 62 percent / aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 13 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: NaN3 / H2O 13: 62 percent / aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 12: 62 percent / aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: NaN3 / H2O 12: 62 percent / aq. KOH / toluene / 2 h / 100 °C

Reference: [1]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[2]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[3]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[4]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[5]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[6]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[7]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[8]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
  • 27
  • [ 6500-65-8 ]
  • B,D-bis-homo-3-methoxy-11-thia-15-azoestra-1,3,5(10),8,14-pentaene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether 7: 96 percent / PhCO2Ag, Et3N 8: KOH / methanol / 4 h / Heating 9: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 10: aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 10 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether 7: 96 percent / PhCO2Ag, Et3N 8: KOH / methanol / 4 h / Heating 9: NaN3 / H2O 10: aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 16 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 16: aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 16 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: NaN3 / H2O 16: aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 16 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 16: aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 16 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: NaN3 / H2O 16: aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether 12: 96 percent / PhCO2Ag, Et3N 13: KOH / methanol / 4 h / Heating 14: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h 15: aq. KOH / toluene / 2 h / 100 °C
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether 12: 96 percent / PhCO2Ag, Et3N 13: KOH / methanol / 4 h / Heating 14: NaN3 / H2O 15: aq. KOH / toluene / 2 h / 100 °C

Reference: [1]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[2]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[3]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[4]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[5]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[6]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[7]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[8]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
  • 28
  • [ 6500-65-8 ]
  • 3-(9-Methoxy-3-methyl-4-oxo-2,3,4,5,6,7-hexahydro-1-thia-dibenzo[a,c]cyclohepten-3-yl)-propionitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol
Multi-step reaction with 9 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol
Multi-step reaction with 9 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol
Multi-step reaction with 8 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol

  • 29
  • [ 6500-65-8 ]
  • [ 153265-26-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 6 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: NaN3 / H2O
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: NaN3 / H2O
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: NaN3 / H2O
Multi-step reaction with 11 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 11 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: NaN3 / H2O

Reference: [1]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[2]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[3]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[4]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[5]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[6]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[7]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[8]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
  • 30
  • [ 6500-65-8 ]
  • [ 153265-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol
Multi-step reaction with 10 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol
Multi-step reaction with 10 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol
Multi-step reaction with 9 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol

  • 31
  • [ 6500-65-8 ]
  • [ 153264-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether 7: 96 percent / PhCO2Ag, Et3N 8: KOH / methanol / 4 h / Heating 9: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 9 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether 7: 96 percent / PhCO2Ag, Et3N 8: KOH / methanol / 4 h / Heating 9: NaN3 / H2O
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: NaN3 / H2O
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: NaN3 / H2O
Multi-step reaction with 14 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether 12: 96 percent / PhCO2Ag, Et3N 13: KOH / methanol / 4 h / Heating 14: 1.) NaN3 / 1.) H2O, 2.) toluene, 100 deg C, 2 h
Multi-step reaction with 14 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether 12: 96 percent / PhCO2Ag, Et3N 13: KOH / methanol / 4 h / Heating 14: NaN3 / H2O

Reference: [1]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[2]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[3]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[4]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[5]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[6]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[7]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
[8]Mandal, Asok N.; Ghosh, Arindam; Bhattacharyya, Sudin; Patra, Ranjan; Chatterjee, Amareshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1004 - 1012]
  • 32
  • [ 6500-65-8 ]
  • [ 153265-08-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether 7: 96 percent / PhCO2Ag, Et3N 8: KOH / methanol / 4 h / Heating
Multi-step reaction with 14 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating
Multi-step reaction with 14 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating
Multi-step reaction with 13 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether 12: 96 percent / PhCO2Ag, Et3N 13: KOH / methanol / 4 h / Heating

  • 33
  • [ 6500-65-8 ]
  • [ 153265-30-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether 7: 96 percent / PhCO2Ag, Et3N
Multi-step reaction with 13 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N
Multi-step reaction with 13 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether 12: 96 percent / PhCO2Ag, Et3N

  • 34
  • [ 6500-65-8 ]
  • 3-(4-Diazo-3-oxo-butyl)-9-methoxy-3-methyl-2,3,6,7-tetrahydro-5H-1-thia-dibenzo[a,c]cyclohepten-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether
Multi-step reaction with 11 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether

  • 35
  • [ 6500-65-8 ]
  • 3-(9-Methoxy-3-methyl-4-oxo-2,3,4,5,6,7-hexahydro-1-thia-dibenzo[a,c]cyclohepten-3-yl)-propionyl azide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: NaN3 / H2O
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: NaN3 / H2O
Multi-step reaction with 12 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: NaN3 / H2O
Multi-step reaction with 11 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: NaN3 / H2O

  • 36
  • [ 6500-65-8 ]
  • 4-(9-Methoxy-3-methyl-4-oxo-2,3,4,5,6,7-hexahydro-1-thia-dibenzo[a,c]cyclohepten-3-yl)-butyryl azide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C 6: 77 percent / NEt3 / diethyl ether 7: 96 percent / PhCO2Ag, Et3N 8: KOH / methanol / 4 h / Heating 9: NaN3 / H2O
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: NaN3 / H2O
Multi-step reaction with 15 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C 12: 77 percent / NEt3 / diethyl ether 13: 96 percent / PhCO2Ag, Et3N 14: KOH / methanol / 4 h / Heating 15: NaN3 / H2O
Multi-step reaction with 14 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C 11: 77 percent / NEt3 / diethyl ether 12: 96 percent / PhCO2Ag, Et3N 13: KOH / methanol / 4 h / Heating 14: NaN3 / H2O

  • 37
  • [ 6500-65-8 ]
  • C22H26O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 79 percent / benzene / 12 h / Heating 2: 76 percent / PPA / 0.33 h / 100 °C 3: 0.65 g / 2-methyl-propan-2-ol 4: KOH / methanol 5: NEt3 / acetone / 0 °C
Multi-step reaction with 11 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: gl. AcOH, NH2OH*HCl / 0.25 h / 170 °C 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C
Multi-step reaction with 11 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 74 percent / NaBH4, pyridine 6: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 7: 90 percent / HCl / 16 h / -5 °C 8: 100 percent / aq. HCl / acetic acid / 7 h / Heating 9: 0.65 g / 2-methyl-propan-2-ol 10: KOH / methanol 11: NEt3 / acetone / 0 °C
Multi-step reaction with 10 steps 1: 3.3 g / p-toluenesulphonic acid / benzene / 12 h / Heating 2: 89 percent / P2O5, 85percent aq. H3PO4 / 0.42 h / 100 °C 3: 81 percent / NaOMe / benzene / 30 °C 4: 1.) gl. AcOH, NH2O2*HCl, 2.) NaOMe / 1.) benzene, 30 deg C, 2.) CH3OH, Et2O 5: 95 percent / NaOMe / methanol / 1 h / Ambient temperature 6: 90 percent / HCl / 16 h / -5 °C 7: 100 percent / aq. HCl / acetic acid / 7 h / Heating 8: 0.65 g / 2-methyl-propan-2-ol 9: KOH / methanol 10: NEt3 / acetone / 0 °C

  • 38
  • [ 6500-65-8 ]
  • [ 36112-55-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 98 percent / NaBH4 / methanol; H2O / 0 °C 2: 89 percent / DMSO
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: TsOH / benzene
  • 39
  • [ 6500-65-8 ]
  • [ 113748-87-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 20 h 2: aq. HCl / ethanol / 4 h / Heating
  • 40
  • [ 6500-65-8 ]
  • 8-Bromo-3-methoxy-9-phenyl-6,7-dihydro-5H-benzocycloheptene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / 20 h 2: aq. HCl / ethanol / 4 h / Heating 3: pyridine hydrobromide perbromide / CH2Cl2 / 3 h
  • 41
  • [ 6500-65-8 ]
  • [ 113748-88-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / 20 h 2: aq. HCl / ethanol / 4 h / Heating 3: pyridine hydrobromide perbromide / CH2Cl2 / 3 h 4: Pd(PPh3)4 / tetrahydrofuran; diethyl ether; cyclohexane / 2 h / Heating 5: pyridine hydrochloride / 2 h / 200 °C
  • 42
  • [ 6500-65-8 ]
  • [ 113748-86-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / 20 h 2: aq. HCl / ethanol / 4 h / Heating 3: pyridine hydrobromide perbromide / CH2Cl2 / 3 h 4: Pd(PPh3)4 / tetrahydrofuran; diethyl ether; cyclohexane / 2 h / Heating
  • 43
  • [ 6500-65-8 ]
  • [ 113748-78-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: tetrahydrofuran; diethyl ether / 20 h 2: aq. HCl / ethanol / 4 h / Heating 3: pyridine hydrobromide perbromide / CH2Cl2 / 3 h 4: Pd(PPh3)4 / tetrahydrofuran; diethyl ether; cyclohexane / 2 h / Heating 5: pyridine hydrochloride / 2 h / 200 °C 6: 1.) NaH / 1) DMF, 25 --> 65 deg C; 2) DMF, 1 h, 65 deg C
  • 44
  • [ 6500-65-8 ]
  • [ 36112-63-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / Br2 / diethyl ether / 2.5 h / 0 - 5 °C 2: 1.6 g / LiCl, Li2CO3 / dimethylformamide / 2.5 h / 130 - 135 °C
Multi-step reaction with 4 steps 1: LiAlH4 / diethyl ether 2: TsOH / benzene 3: NBS, (PhCO)2O2 / CCl4 / Irradiation 4: SeO2, aq. KH2PO4 / dioxane
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: lithium chloride / N,N-dimethyl-formamide / Reflux
  • 45
  • [ 6500-65-8 ]
  • [ 84574-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / Br2 / diethyl ether / 2.5 h / 0 - 5 °C 2: 1.6 g / LiCl, Li2CO3 / dimethylformamide / 2.5 h / 130 - 135 °C 3: 87 percent / xylene / 22 h / Heating
  • 47
  • [ 6500-65-8 ]
  • [ 77607-60-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 100 percent / p-TsOH / benzene / 0.5 h / Heating
Multi-step reaction with 4 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 0.2 g / HCl gas / ethanol / 168 h / Ambient temperature
  • 48
  • [ 6500-65-8 ]
  • [ 77607-63-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 100 percent / p-TsOH / benzene / 0.5 h / Heating 5: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate
Multi-step reaction with 5 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 0.2 g / HCl gas / ethanol / 168 h / Ambient temperature 5: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate
  • 49
  • [ 6500-65-8 ]
  • [ 77607-58-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature
  • 50
  • [ 6500-65-8 ]
  • [ 104062-80-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature
  • 51
  • [ 6500-65-8 ]
  • 1,2-trans-1-(p-hydroxyphenyl)-2-benzyl-7-methoxy-benzosuberan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 51 percent / HCl gas / ethanol / 168 h / Ambient temperature
  • 52
  • [ 6500-65-8 ]
  • 1,2-trans-1-(o-hydroxyphenyl)-2-benzyl-7-methoxy-benzosuberan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 7 percent / HCl gas / ethanol / 168 h / Ambient temperature
  • 53
  • [ 6500-65-8 ]
  • [ 77607-64-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 51 percent / HCl gas / ethanol / 168 h / Ambient temperature 5: 82 percent / pyridine / 24 h
  • 54
  • [ 6500-65-8 ]
  • [ 77607-65-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 7 percent / HCl gas / ethanol / 168 h / Ambient temperature 5: 90 percent / pyridine / 24 h
  • 55
  • [ 6500-65-8 ]
  • [ 77607-66-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KOH / methanol / 1.) 10 deg C, 30 min, 2.) room temperature, 4 h 2: 100 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 760 Torr / Ambient temperature 3: 99 percent / KBH4 / methanol / 4 h / Ambient temperature 4: 51 percent / HCl gas / ethanol / 168 h / Ambient temperature 5: 80 percent / K2CO3 / acetone / 24 h / Heating
  • 56
  • [ 6500-63-6 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 23 g / hydrogen / 10percent Pd-C / ethanol / 760 Torr / Ambient temperature 2: PCl5 / benzene / 0.5 h / Heating 3: SnCl4 / benzene / 24 h / Ambient temperature
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / ethanol 2: (i) PCl5, benzene, (ii) SnCl4
Multi-step reaction with 2 steps 1: nickel/aluminium alloy; sodium hydroxide 2: polyphosphoric acid
  • 57
  • [ 591-31-1 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) t-BuOK, 2.) aq. KOH / 1.) t-BuOH, 4 h, 2.) reflux, 12 h 2: 23 g / hydrogen / 10percent Pd-C / ethanol / 760 Torr / Ambient temperature 3: PCl5 / benzene / 0.5 h / Heating 4: SnCl4 / benzene / 24 h / Ambient temperature
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate 2: nickel/aluminium alloy; sodium hydroxide 3: polyphosphoric acid
  • 58
  • [ 6500-65-8 ]
  • bicyclo[5.4.0]undec-2-en-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C 3: ethanol / 1.) 3 h, reflux, 2.) 12 h, RT 4: n-BuLi / tetrahydrofuran / 0 - 5 °C 5: Me3SiCl, NaI, pyridine / acetonitrile / 14 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C
  • 59
  • [ 6500-65-8 ]
  • [ 115462-86-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C 3: ethanol / 1.) 3 h, reflux, 2.) 12 h, RT 4: n-BuLi / tetrahydrofuran / 0 - 5 °C 5: Me3SiCl, NaI, pyridine / acetonitrile / 14 h / Ambient temperature
  • 60
  • [ 6500-65-8 ]
  • 9-methoxybicyclo<5.4.0>undec-2-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C 3: ethanol / 1.) 3 h, reflux, 2.) 12 h, RT 4: n-BuLi / tetrahydrofuran / 0 - 5 °C
  • 61
  • [ 6500-65-8 ]
  • 9-methoxybicyclo<5.4.0>undecan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C
  • 62
  • [ 6500-65-8 ]
  • (1R,4aS,5R,6R,9aS)-6-Methoxy-decahydro-1,5-cyclo-benzocyclohepten-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C 3: ethanol / 1.) 3 h, reflux, 2.) 12 h, RT 4: n-BuLi / tetrahydrofuran / 0 - 5 °C 5: Me3SiCl, NaI, pyridine / acetonitrile / 14 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 7: NBS / 24 h / Ambient temperature 8: 90 percent / NaH / dimethylsulfoxide / 1 h / 70 °C
  • 63
  • [ 6500-65-8 ]
  • 2-bromo-3-methoxybicyclo<5.4.0>undecan-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C 3: ethanol / 1.) 3 h, reflux, 2.) 12 h, RT 4: n-BuLi / tetrahydrofuran / 0 - 5 °C 5: Me3SiCl, NaI, pyridine / acetonitrile / 14 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 7: NBS / 24 h / Ambient temperature
  • 64
  • [ 6500-65-8 ]
  • 2-bromo-3-acetoxybicyclo<5.4.0>undecan-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C 3: ethanol / 1.) 3 h, reflux, 2.) 12 h, RT 4: n-BuLi / tetrahydrofuran / 0 - 5 °C 5: Me3SiCl, NaI, pyridine / acetonitrile / 14 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 7: NBS / acetic acid; acetic anhydride / 24 h / Ambient temperature
  • 65
  • [ 6500-65-8 ]
  • [ 115462-84-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) H2 / 1.) Ru on Al2O3 (5percent) / 80 °C / 76000.1 Torr 2: Al-isopropoxide, acetone / toluene / 48 h / 90 °C 3: ethanol / 1.) 3 h, reflux, 2.) 12 h, RT
  • 66
  • [ 591-31-1 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: K, tBuOH 2: H2 / Raney-Ni / ethanol 3: (i) PCl5, benzene, (ii) SnCl4
  • 68
  • [ 6500-65-8 ]
  • [ 36112-61-5 ]
  • 69
  • [ 6500-65-8 ]
  • cis-2-Hydroxy-6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: AlCl3 2: (i) K2CO3, acetone, (ii) nBuONO, KOEt, Et2O 3: LiAlH4 4: H2, AcOH / Pd-C
  • 70
  • [ 50886-32-3 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis-(2-methoxy-ethyl) ether 2: NaOH / methanol 3: Zn, Cu(OAc)2 / acetic acid
  • 71
  • [ 50683-07-3 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaOH / methanol 2: Zn, Cu(OAc)2 / acetic acid
  • 72
  • [ 1078-19-9 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: TsOH 2: bis-(2-methoxy-ethyl) ether 3: NaOH / methanol 4: Zn, Cu(OAc)2 / acetic acid
  • 73
  • [ 6500-65-8 ]
  • [ 917591-79-8 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 1-bromo-3,4,5-trimethoxybenzene With n-butyllithium In diethyl ether at -78 - -30℃; Stage #2: 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one In diethyl ether at -30 - 20℃; 1 2-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-ol (32) 2-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-ol (32) 200 mL of anhydrous ether was, added to 3,4,5-trimethoxybromobenzene (1.23 g, 4.97 mmol) in a 500 mL round bottom flask under nitrogen. The temperature of the reaction mixture was brought to -78° C. n-Butyllithium (4.5 mL, 11.25 mmol) was added dropwise. The reaction mixture was then stirred until the temperature was raised gradually to -30° C. 30 (0.86 g, 4.5 mmol) dissolved in 25 mL of dry ether was added dropwise and the reaction mixture was allowed to stir until the temperature warmed up to room temperature. 25 mL of water was added and the product was extracted with ether (3*50), combined organic phases were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Purification by column chromatography (silica gel, 20:80 EtOAc:Hexanes) yielded 800 mg (49%) of 32 as pale yellow oil Rf: 0.16 (30:70, EtOAc:Hexanes).
  • 74
  • [ 21336-18-5 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
25% With chromium(VI) oxide; acetic acid In water at 20℃; for 24h; 1 2-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one (30) 2-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one (30) 29 (3.42 g, 19.4 mmol) was taken in a 500 mL round bottom flask, and to this was added 40 mL of glacial acetic acid followed by a CrO3 (5.82 g, 58.21 mmol) dissolved in 5 mL of water and 20 mL of acetic acid dropwise. After the addition was completed, the reaction mixture was stirred for 24 h at room temperature. 100 mL of water was added to the reaction mixture and then extracted with ether (100*3). The combined ethereal extracts were then washed with 5% NaOH solution, until the aqueous phases were alkaline. The organic phase was washed with water until neutral and then dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Purification by flash column chromatography (neutral alumina) afforded 910 mg (25%) of product as colorless oil. Product obtained in 10:90 (EtOAc:Hexanes). 1H NMR (CDCl3, 300 MHz): δ 7.79 (d, J=8.58 Hz, 1H), 6.81 (dd, J=8.70 Hz, 2.66 Hz, 1 H), δ 6.70 (d, J=2.68 Hz, 1 H), δ 3.84 (s, 3 H), δ 2.91(m, 2 H), δ 2.72 (m, 2H), δ 1.84 (m, 4 H).
  • 75
  • [ 6500-65-8 ]
  • [ 2675-79-8 ]
  • [ 917591-79-8 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 1-bromo-3,4,5-trimethoxybenzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one In tetrahydrofuran; hexanes at -78 - 20℃; Stage #3: With water In tetrahydrofuran; hexanes at 20℃; A.49 49. 2-Methoxy-5-(3',4',5'-trimethoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclobenzoheptan-5-ol (49) To a solution of 3,4,5-trimethoxyphenylbromide (5.05 g, 20.4 mmol) in anhydrous THF (150 mL) at -78° C., n-BuLi (8.5 mL, 2.5 M in hexanes) was added and the reaction stirred for 30 min. Benzosuberone 48 (2.10 g, 11.0 mmol) in 25 mL THF was added using a dropping funnel over a period of 15 min. The reaction mixture was stirred overnight and allowed to warm to ambient temperature. On completion, the reaction mixture was quenched with H2O (100 mL), and extracted with Et2O (150 mL) and EtOAc (15 mL). The combined organic phase was washed with brine, dried over MgSO4, filtered, and evaporated under reduced pressure. Flash chromatography of the crude product using a prepacked 25 g silica column [eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 25% A/75% B over 1.39 min (1 CV), 25% A/75% B 80% A/20% B over 16.3 min (10 CV), 80% A/20% B over 5.18 min (2 CV); flow rate 25.0 mL/min; monitored at λλ254 and 280 nm] afforded alcohol 49 (3.81 g, 10.6 mmol, 96% yield) as a white solid. 1H NMR (CDCl3, 500 MHz): δ 7.27 (1H, d, J=8.8 Hz, H-4), 6.79 (1H, d, J=8.7 Hz, H-3), 6.48 (2H, s, H-2', H-6'), 3.90 (3H, s, OCH3-2), 3.85 (3H, s, OCH3-4'), 3.76 (6H, s, OCH3-3', -5'), 3.16 (1H, m, CH2-9), 2.37 (1H, m, CH2-9), 2.57 (1H, m, CH2-8). 2.11 (1H, m, CH2-8), 1.94 (1H, s, CH2-716), 1.77 (2H, m, CH2-6, CH2-7), 1.49 (1H, m, H-6/7). 13C NMR (CDCl3, 125 MHz): δ 153.1 (C, C-3', C-5'), 149.6 (C, JC-F=2.0 ppm, C-1), 146.7 (C, C-2), 141.1 (C, C-1'), 137.4 (CH, C-4'), 138.8 (CH, C-4-a), 129.1 (C, C-1a), 122.1 (C, C-4), 109.4 (C, C-1), 104.2 (CH, C-2', C-6'), 79.8 (C, C-5), 60.8 (CH3, OCH3-4'), 56.1 (CH3, OCH3-3', -5'), 56.0 (CH3, OCH3-2), 41.2 (CH, C-6), 26.6 (CH2, CH2-817), 26.2 (CH2, CH2-718), 24.2 (CH2, CH2-9).
76% Stage #1: 1-bromo-3,4,5-trimethoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere; 51 4.1.1.51. 2-Methoxy-5-(30,40,50-trimethoxyphenyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol (20) 4.1.1.51 2-Methoxy-5-(3',4',5'-trimethoxyphenyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol (20)30,31,56 To an oven dried flask, THF (50 mL) and 3,4,5-trimethoxyphenyl bromide (2.82 g, 11.4 mmol) were added, and the solution was cooled to -78 °C. n-BuLi (4.9 mL,12 mmol) was slowly added to the reaction mixture, which was then stirred at -78 °C for 1 h. Benzosuberone 14 (1.60 g, 8.41 mmol) was then added dropwise to the flask, and the reaction mixture was stirred while warming from -78 °C to room temperature over 12 h. The reaction mixture was washed with water and extracted with EtOAc (3 * 50 mL). The combined organic phase was dried over sodium sulfate and evaporated under reduced pressure. The crude reaction product was purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 10% A/90% B (1 CV), 10% A/90% B → 60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 50 mL/min; monitored at 254 and 280 nm] to afford tertiary alcohol 20 (2.29 g, 6.48 mmol, 76%) as a light yellow oil. NMR characterization was performed after the next step.
50% Stage #1: 1-bromo-3,4,5-trimethoxybenzene With n-butyllithium In diethyl ether at -78 - -30℃; Stage #2: 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one In diethyl ether at -30 - 20℃; Further stages.;
  • 76
  • [ 6500-65-8 ]
  • [ 17356-08-0 ]
  • [ 1172115-45-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one With phenyltrimethylammonium tribromide Stage #2: thiourea 1 Compound 42:Compound 421H NMR (300 MHz, CDCl3) δ 11.3 (br s, IH, NH), 7.69 (d, J = 8.5 Hz, IH), 7.34-7.26 (m, IH), 6.78 (t, J= 8.2 Hz, 2H), 6.76 (dd, J= 8.2, 2.8 Hz, IH), 6.63 (d, J= 2.8 Hz, IH), 3.84 (s, 3H), 2.93 (t, J = 7.2 Hz), 2.66-2.62 (m, 2H), 2.18-2.10 (m, 2H). MS (ESI) [M+H+]: 387.
  • 77
  • [ 6500-65-8 ]
  • 8-bromo-3-methoxy-6,7-dihydro-5H-benzo[7]annulen-9-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bromine / diethyl ether / 2 h 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 - 0 °C
Multi-step reaction with 2 steps 1.1: bromine / diethyl ether / 1 h / 0 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -70 °C / Inert atmosphere 2.2: 20 h / 20 °C
Multi-step reaction with 2 steps 1.1: bromine / diethyl ether / 1 h / 0 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -70 °C / Inert atmosphere 2.2: 20 h / 20 °C / Inert atmosphere
  • 78
  • [ 6500-65-8 ]
  • [ 1373132-91-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bromine / diethyl ether / 2 h 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 - 0 °C 3.1: potassium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 15 h / Reflux
  • 79
  • [ 6500-65-8 ]
  • [ 1373132-92-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: bromine / diethyl ether / 2 h 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 - 0 °C 3.1: potassium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 15 h / Reflux 4.1: sodium hydroxide; water / 20 °C
  • 80
  • [ 6500-65-8 ]
  • [ 1373132-93-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: bromine / diethyl ether / 2 h 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 - 0 °C 3.1: potassium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 15 h / Reflux 4.1: sodium hydroxide; water / 20 °C 5.1: pyridine hydrochloride / 1 h / 200 °C
  • 81
  • [ 6500-65-8 ]
  • [ 1373132-94-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: bromine / diethyl ether / 2 h 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 - 0 °C 3.1: potassium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 15 h / Reflux 4.1: sodium hydroxide; water / 20 °C 5.1: pyridine hydrochloride / 1 h / 200 °C 6.1: triethylamine / dichloromethane / 1 h / -10 °C
  • 82
  • <3-carbomethoxy-propen-(2)-yl-(1)>-triphenylphosphoniumbromide [ No CAS ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / methanol / 5 h / Reflux 2.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 2 h / 20 °C / 2585.81 Torr 3.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 15 h / -5 - 20 °C 3.2: pH 2 - 3 4.1: PPA / chlorobenzene / 15 h / 80 °C
  • 83
  • [ 226719-69-3 ]
  • [ 6500-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 2 h / 20 °C / 2585.81 Torr 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 15 h / -5 - 20 °C 2.2: pH 2 - 3 3.1: PPA / chlorobenzene / 15 h / 80 °C
  • 84
  • [ 6500-65-8 ]
  • [ 71089-18-4 ]
  • [ 71089-19-5 ]
YieldReaction ConditionsOperation in experiment
1: 30% 2: 41% With nitric acid; acetic anhydride In acetic acid at -78℃; for 3h; B.1 1. 1-Nitro-2-Methoxy-6,7,8,9-tetrahydro-5H-cyclobenzoheptan-5-one (3) To a solution of benzosuberone 48 (0.533 g, 2.80 mmol) in acetic anhydride (5 mL) cooled to -78° C., a solution (1:1) of HNO3 and acetic acid (1.00 mL) was added dropwise, while stirring the solution. The reaction mixture was allowed to stir for 3 h and then ice cold water was added to quench the reaction. The mixture was stirred vigorously for 2 min and the organic layer was separated. Aqueous layer was extracted with EtOAc (2*25 mL). Combined organic phase was washed with brine, dried over MgSO4, filtered and the solvents evaporated on a rotavapor. Flash chromatography of the crude using a prepacked 50 g silica column; Eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 20% A/80% B over 3.18 min (1 CV), 20% A/80% B 80% A/20% B over 33.0 min (10 CV), 80% A/20% B over 6.36 min (2 CV); flow rate 40.0 mL/min; monitored at λλ254 and 280 nm; afforded 1-nitrobenzosuberone 3 (0.201 g, 0.854 mmol, 30%) and 3-nitro benzosuberone 76 (0.268 g, 1.14 mmol, 41%). 1H NMR (1-nitro benzosuberone 3) (500 MHz, CDCl3) δ 7.84 (1H, d, J=8.8 Hz, H-4), 6.97 (1H, d, J=8.8 Hz, H-3), 3.94 (3H, s, OCH3-2), 2.79 (2H, dd, J=6.5 Hz, H-9), 2.72 (2H, dd, J=6.0 Hz, H-6), 1.92 (2H, m, J=6.5 Hz, H-8), 1.82 (2H, m, J=6.0 Hz, H-7); 13C NMR (126 MHz, CDCl3) δ 203.1 (C, C-5), 153.3 (C, C-2), 141.4 (C, C-1), 134.0 (C, C-1a), 132.2 (C, C-4-a), 131.9 (C, C-4), 110.3 (C, C-3), 56.6 (CH3, OCH3-2), 40.3 (C, C-6), 26.2 (C, C-9), 24.4 (C, C-8), 20.2 (C, C-7); Anal., Calcd for C12H13NO4: C, 61.27; H, 5.57; N, 5.82. Found: C, 61.17; H, 5.55; N, 5.82; HRMS, m/z: observed 236.0919 [M+1]+, (calcd for C12H14NO4+, 236.0917). 1H NMR (3-nitro benzosuberone 76) (500 MHz, CDCl3) δ 8.32 (1H, s, H-4), 6.88 (1H, s, H-1), 4.01 (3H, s, OCH3-2), 2.99 (2H, dd, J=6.6, 6.3 Hz, H-9), 2.76 (2H, dd, J=6.1, 4.1 Hz, H-6), 1.94 (2H, m, J=6.6, 6.3 Hz, H-8), 1.84 (2H, m, J=6.1, 4.1 Hz, H-7); 13C NMR (126 MHz, CDCl3) δ 202.0 (C, C-5), 155.1 (C, C-2), 148.8 (C, C-1a), 138.2 (C, C-3), 131.0 (C, C-4-a), 127.3 (C, C-4), 114.1 (C, C-1), 56.7 (CH3, OCH3-2), 40.4 (C, C-6), 33.1 (C, C-9), 24.7 (C, C-8), 20.3 (C, C-7); HRMS, m/z: observed 236.0921 [M+1]+, (calcd for C12H14NO4+, 236.0917).
1: 37% 2: 41% With nitric acid; acetic anhydride; acetic acid at -10℃;
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