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CAS No. : | 36039-36-8 | MDL No. : | MFCD08275583 |
Formula : | C13H20O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IZXWIWYERZDWOA-UHFFFAOYSA-N |
M.W : | 192.30 | Pubchem ID : | 595160 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate; zwitterionic rhodium ν6-tetraphenylborate; isopropyl alcohol In dichloromethane at 100℃; for 22h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With Dess-Martin periodane In dichloromethane Inert atmosphere; | |
80% | With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃; | |
74% | With Dess-Martin periodane In dichloromethane at 20℃; for 1h; Inert atmosphere; |
54% | With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1h; | |
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1) -65 deg C, CH2Cl2, 5 min; Multistep reaction; | ||
327 mg | With pyridinium chlorochromate In dichloromethane for 1.5h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With oxygen | |
87% | With dipyridinium dichromate In N,N-dimethyl-formamide at 20℃; for 12h; | |
77.6% | With sodium hydroxide; oxygen; lead acetate In water at 110℃; for 4.5h; |
72% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water; acetone at 20℃; for 168h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; | |
99% | With lithium aluminium tetrahydride In diethyl ether at 0℃; Inert atmosphere; | |
98% | With dimethylsulfide borane complex In diethyl ether at 0℃; |
95% | With lithium aluminium tetrahydride In tetrahydrofuran Reflux; | |
94% | With lithium aluminium tetrahydride In diethyl ether at 10℃; for 4h; | |
91% | With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | |
82% | With tin(II) trifluoromethanesulfonate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In water; toluene at 160℃; for 48h; Autoclave; | |
Multi-step reaction with 2 steps 2: NaBH4, CaCl2 / ethanol / -20 °C | ||
11 Preparation 11 Preparation 11 2-[4-(2-Methylpropyl)phenyl]-propan-1-ol. The title compound was prepared by the procedure of Preparation 2 in quantitative yield from α-methyl-4-(2-methylpropyl)benzeneacetic acid which is Ibuprofen and lithium aluminum hydride. | ||
With dimethylsulfide borane complex | ||
Multi-step reaction with 2 steps 1: (4-Me)Triaz(NHP<SUP>i</SUP>Pr<SUB>2</SUB>)<SUB>2</SUB>Mn(CO)<SUB>2</SUB>Br / toluene / 6 h / 25 °C / Inert atmosphere 2: silica gel; water / methanol / 60 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 65 °C / Inert atmosphere 2: methanol; sodium tetrahydroborate / 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / 0 °C 1.2: Reflux 2.1: lithium aluminium tetrahydride / diethyl ether / 20 °C / Inert atmosphere | ||
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With methanol; Na/SiO<SUB>2</SUB> In tetrahydrofuran at 0 - 25℃; Inert atmosphere; | |
95% | With isopropyl alcohol In hexane at 0 - 20℃; for 0.25h; Inert atmosphere; | |
88% | With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; |
With sodium tetrahydroborate; calcium chloride In ethanol at -20℃; | ||
With sodium tetrahydroborate In methanol for 4h; | ||
85 %Spectr. | With methanol; thulium(II) iodide In tetrahydrofuran at 23℃; Inert atmosphere; Schlenk technique; | |
With methanol; sodium tetrahydroborate at 20℃; Inert atmosphere; | ||
With C22H14MnN2O4(1+)*BF4(1-); potassium hydride In tetrahydrofuran at 50℃; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide Yield given. Multistep reaction; | ||
Multi-step reaction with 2 steps 1: oxygen; water; palladium dichloride; hydrogenchloride / dimethyl sulfoxide / 24 h / 100 °C / 760.05 Torr / Green chemistry 2: hydrogen; palladium on activated charcoal / methanol / 6 h / 20 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride In diethyl ether | ||
With lithium aluminium tetrahydride In diethyl ether at 20℃; Inert atmosphere; | 3.1.1. General Synthesis of Compounds b, d, f, h, j and l General procedure: To a cooled (0 C) solution of 1 mmol of a, c, e, g, i, or k in dry dichloromethane,1.1 mmol N,N-dicyclohexylcarbodiimide was added and the reaction mixture was stirredat 0 C for 20-90 min. The mixture was then brought to room temperature and 10 mmolabsolute ethanol was added dropwise. After the addition, the reaction mixture washeated at reflux for 4-24 h, after which it was diluted with dichloromethane, washed withwater, NaHCO3 5% solution and brine. The organic phase was dried over anhydroussodium sulfate and evaporated to dryness. The crude product was purified by flashchromatography to give an ethyl ester of a, c, e, g, i, and k, respectively. Subsequently,1 mmol of the respective ethyl ester was dissolved in dry diethylether and was addeddropwise to a suspension of 1.2 mmol lithium aluminum hydride in dry diethylether, underArgon. The reaction mixture was stirred at room temperature for 1-2 h and then dilutedwith ethyl acetate and ltered. The precipitate was thoroughly washed with diethylether.The filtrate was diluted with diethylether and washed with H2SO4 15% solution, water,NaHCO3 5% solution and water, dried over anhydrous sodium sulfate and evaporated todryness. The crude product was purified by flash chromatography to give pure b, d, f, h, j,and l.2-(4-Isobutylphenyl)propanoic acid (b) Total yield: 62%, colorless oil. 1H-NMR (CDCl3,200 MHz), (ppm): 0.90 (d, J = 6.8 Hz, 6Hz, -CH(CH3)2), 1.26 (d, J = 7.2 Hz, 3H, -CH(CH3)),1.36 (brs, 1H, -OH), 1.85 (sep, J = 6.4 Hz, 1H, -CH(CH3)2), 2.45 (d, J = 7.2 Hz, 2H, -CH-CH2-),2.93 (sex, J = 6.8 Hz, 1H, -CH(CH3)), 3.68 (d, J = 4.4 Hz, 2H, -CH2OH), 7.11-7.15 (4H,aromatic). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 65% 2: 15% | With diisobutylaluminium hydride In diethyl ether; hexane at -78℃; | |
1: 65% 2: 15% | With diisobutylaluminium hydride In diethyl ether; hexane at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine; DMAP / CH2Cl2 / 1 h / 20 °C 2: pig pancreatic lipase; phosphate buffer / acetone / pH 8.0 3: pyridinium dichromate / dimethylformamide / 72 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; DMAP / CH2Cl2 / 1 h / 20 °C 2: pig pancreatic lipase; phosphate buffer / acetone / pH 8.0 | ||
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: horse liver alcohol dehydrogenase; NADP; isopropyl alcohol / aq. phosphate buffer / 24 h / 30 °C / pH 7.5 / Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; DMAP / CH2Cl2 / 1 h / 20 °C 2: pig pancreatic lipase; phosphate buffer / acetone / pH 8.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C 2: 68 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran / 18 h / Heating 3: 1.) borane-dimethyl sulfide, 2.) H2O2/NaOH | ||
Multi-step reaction with 3 steps 1: 87 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C 2: 73 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran 3: 1.) borane-dimethyl sulfide, 2.) H2O2/NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 68 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran / 18 h / Heating 2: 1.) borane-dimethyl sulfide, 2.) H2O2/NaOH | ||
Multi-step reaction with 2 steps 1: 73 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran 2: 1.) borane-dimethyl sulfide, 2.) H2O2/NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) oxalyl chloride, DMSO, 2) Et3N / 1) -65 deg C, CH2Cl2, 5 min 2: 40 percent / potassium acetate / aq. ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) oxalyl chloride, DMSO, 2) Et3N / 1) -65 deg C, CH2Cl2, 5 min 2: 20 percent / potassium acetate / aq. ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) oxalyl chloride, DMSO, 2) Et3N / 1) -65 deg C, CH2Cl2, 5 min 2: 56 percent / potassium acetate / aq. ethanol / 0.33 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: tert-butyl 2-(4-isobutylphenyl)propanoate With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: With water; Rochelle's salt In tetrahydrofuran for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 15% 2: 15% 3: 44% | With sodium tungstate; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate at 90℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: formaldehyd; p-isobutylstyrene With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In toluene at 80℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; iron(II) In water at 20℃; | 3. Fenton degradation General procedure: For the Fenton degradation experiment, 10 mL of a Milli Q water sample acidified at pH 2 with 100 µL H2SO4 0.5 mol/L containing 200 ng of each studied anti-inflammatory drug (diclofenac sodium, ibuprofen and ketoprofen) was placed into a 50 mL brown glass bottle. Immediately, 500 µL of Fe2+solution (1 mg/mL Fe2+) and 200 µL of H2O2 (30%) were added into the brown bottle which was kept under magnetic stirring and room temperature for different time intervals in order to perform the degradation process. Because the catalyst (Fe2+) and the oxidant (H2O2) are consumed very fast, these were refreshed at each 30 minutes in the same amounts as it was described previously. To study the Fenton oxidative process efficiency over the selected drugs, different experiments at 30, 60 and 120 minutes were performed. After each Fenton oxidative experiment, the degradation by-products of NAIDs were extracted with organic solvent and analyzed by GC×GC-qMS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1,2-bis(dimethylphosphanyl)ethane; potassium <i>tert</i>-butylate; hydrazine hydrate; dimethyl sulfoxide In <i>tert</i>-butyl alcohol at 100℃; for 24h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane 2: sodium iodide; [bis(acetoxy)iodo]benzene / acetonitrile / 2 h / Irradiation; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane 2: sodium iodide; [bis(acetoxy)iodo]benzene / acetonitrile / 2 h / Irradiation; Inert atmosphere 3: hydrogenchloride / methanol; water / 2 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With palladium on activated charcoal; hydrogen In methanol at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; sodium In hexane at 0℃; for 0.333333h; Inert atmosphere; Overall yield = 62 %; Overall yield = 59.6 mg; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: horse liver alcohol dehydrogenase; NADP / aq. phosphate buffer / 24 h / 30 °C / pH 7.5 / Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With water; silica gel In methanol at 60℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With C24H24IrN4O4(1+)*BF4(1-); sodium t-butanolate at 140℃; for 24h; Sealed tube; Inert atmosphere; | General procedure for bis-NHC-Ir-catalyzed β-methylationof primary alcohols General procedure: To a sealed tube (35 mL) equipped witha stir bar, Ir-NHC catalyst 5d (0.05 mol%), methanol (1 mL),tBuONa (2 mmol) and primary alcohol (1 mmol) were addedunder nitrogen atmosphere. The solution was heated at140 °C for 24 h. 1,3,5-Trimethoxybenzene was added as aninternal standard, and sent for nuclear magnetic resonance(NMR) measurement. Pure products were obtained by columnchromatography over silica gel using ethyl acetate/petroleum ether mixture as eluent. |
83% | With [Mn(HN(C2H4PiPr2)2)(CO)2Br]; sodium methylate at 150℃; for 24h; Inert atmosphere; Autoclave; Green chemistry; regioselective reaction; | |
64%Spectr. | With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); sodium methylate at 150℃; for 28h; Inert atmosphere; Autoclave; Glovebox; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With ethanol; sodium In hexane; paraffin oil at 0℃; for 0.0833333h; Inert atmosphere; | 45 Example 45 10mL single mouth bottle, nitrogen protection, adding 0.50mmol of compound 1u,2.5 mL of n-hexane, 10 mmol of ethanol, 2.0 mmol of sodium dispersion reagent (34.1 wt%, suspension of paraffin, particle size <100 μm),Stir at 0 ° C for 5 min and warm to room temperature.The reaction was quenched with saturated aqueous sodium bicarbonate.Adding ether and saturated brine to extract, the organic phase is dried, concentrated, and separated by column chromatography.32.6 mg of the target compound 2u,The yield was 34%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | Stage #1: 2-(4-isobutylphenyl)propan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: bromopentene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: iron(II) diacetylacetonate; scandium tris(trifluoromethanesulfonate); sodium chloride / dichloromethane / 16 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetonitrile / 2 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 °C / Inert atmosphere 3.1: C50H68N8RuSi2(2+)*2F6P(1-); potassium carbonate / chloroform / 16 h / 60 °C / Inert atmosphere; Schlenk technique; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetonitrile / 2 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetonitrile / 2 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 °C / Inert atmosphere 3.1: C50H68N8RuSi2(2+)*2F6P(1-); potassium carbonate / chloroform / 16 h / 60 °C / Inert atmosphere; Schlenk technique; Sealed tube 4.1: water; hydrogenchloride / 0.25 h / Inert atmosphere; Schlenk technique; Sealed tube 4.2: 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(4-isobutylphenyl)propan-1-ol; 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 2h; Inert atmosphere; Stage #2: With 1H-imidazole; hydroxylamine hydrochloride In acetonitrile at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With [Mn(HN(C2H4PiPr2)2)(CO)2Br]; hydrogen; sodium t-butanolate In toluene at 150℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: iodine; triphenylphosphine; 1H-imidazole / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: dimanganese decacarbonyl / dichloromethane / 12 h / 20 °C / Inert atmosphere; Irradiation; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5h; | 3.1.4. General Synthesis of Compounds 14-17 General procedure: To a cooled (0 C) solution of 1 mmol of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid in dry dichloromethane, 3 mmol of the corresponding alcohol b, d, f or n,1.1 mmol N,N-dicyclohexylcarbodiimide and a catalytic amount of dimethylaminopyridinewere added. The reaction mixture was stirred at 0 C for 5 min and at room temperaturefor 5 h (or 3 days for compound 17) and then filtered. The filtrate was diluted withdichloromethane, washed with 0.5N HCl solution and NaHCO3 5% solution, dried overanhydrous sodium sulfate and evaporated to dryness. The crude product was purified byflash chromatography to yield the final compounds 14-17.2-(4-isobutylphenyl)propyl6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylate (14) Yield:94%, white solid. m.p.: 69.2-70.0 C. 1H NMR (400 MHz, CDCl3), (ppm): 0.94 (d, 6H,-CH(CH3)2)), 1.21 (d, 3H, -CH(CH3)), 1.33 (dd, J = 9.0, 5.7 Hz, 1H, -CH(CH3)2), 1.56 (d,J = 3.8 Hz, 3H, 2-CH3), 1.78-1.93 (m, J = 19.3, 8.6, 4.5 Hz, 2H, 3-CH2), 2.06 (d, J = 5.4 Hz, 3H,8-CH3), 2.20 (d, J = 7.8 Hz, 6H, 5,7-CH3), 2.30-2.42 (m, 1H, 1/2x 4-CH2), 2.47 (d, J = 10.7 Hz,2H, -CH2CH(CH3)2), 2.52-2.64 (m, 1H, 1/2 4-CH2), 3.04 (sex, 1H, -CH(CH3)), 4.07-4.16(m, J = 8.8, 6.5, 2.5 Hz, 1H, 1/2 -OCH2-), 4.19-4.30 (m, 1H, 1/2 -OCH2-), 4.36 (brs, 1H,-OH), 7.09 (d, J = 2.4 Hz, 4H, aromatic). 13C NMR (101 MHz, CDCl3), (ppm): 11.22 (5-CH3),11.82 (7-CH3), 12.21 (8-CH3), 17.74 (-CH(CH3)), 20.84 (-C(CH3)), 22.38 (-CH(CH3)2), 25.50(3-CH2), 30.23 ((-CH(CH3)2), 30.60 (4-CH2), 38.55 (-CH(CH3)), 45.04 (-CH2CH(CH3)2), 70.04(-OCH2-), 77.00 (-C(CH3)), 116.89 (4a-chromane), 118.35 (5-chromane), 121.13 (7-chromane),122.49 (8-chromane), 126.96 (3,5-phenyl), 129.14 (2,6-phenyl), 139.99 (4-phenyl), 140.26(1-phenyl), 145.24 (6-chromane), 145.64 (8a-chromane), 173.83 (C=O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | 3.1.3. General Synthesis of Compounds 1-13 General procedure: To a cooled (0 C) solution of 1 mmol of the respective carboxylic acid and 1.3 mmol ofthe corresponding alcohol in dry dichloromethane, 1.1 mmol of N,N-dicyclohexylcarbodiimide and a catalytic amount of dimethylaminopyridine were added. The reaction mixturewas stirred at room temperature for 24 h and then filtered. The filtrate was diluted withdichloromethane and washed with water. The organic phase was dried over anhydroussodium sulfate and evaporated to dryness. The crude product was purified by flashchromatography, to give the final compounds 1-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 1.5 h / Inert atmosphere; Schlenk technique 2: zinc dibromide / dichloromethane / 2 h / 0 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 66 % ee 2: 77 % ee | With (S)-2-((1-methylpyrrolidin-2-yl)methyl)-2,3-dihydro-1H-benzo[de]isoquinoline; triethylamine In dichloromethane at -78℃; for 3h; Molecular sieve; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With bis(1,5-cyclooctadiene)nickel (0); 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 22h; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere; | 5 Intermediate 5g Referring to the synthesis procedure of intermediate 1d in Example 1, white solid 5d was obtained, and then compound 5d (358 mg, 1.58 mmol) and compound 5f (288.4 mg, 1.5 mmol) were added to anhydrous DCM (10 mL) under ice bath condition To the solution, DMAP (37 mg, 0.3 mmol) and DCC (464 mg, 2.25 mmol) were sequentially added and stirred overnight.The DCM was evaporated under reduced pressure, an aqueous solution (40 mL) was added to the residue, which was then extracted with ethyl acetate (3 x 20 mL).The combined organic phases were washed with saturated brine (2×20 mL), and then dried over anhydrous sodium sulfate.The desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluted with ethyl acetate/petroleum ether (0.5%) system) to obtain 5 g (581 mg, yield 97%) of a white solid ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 0.33 h / 0 - 20 °C 2: diethyl ether / 3 h / 0 - 20 °C / Inert atmosphere 3: pyridinium chlorochromate; mesoporous silica / dichloromethane / 3 h / 20 °C / Inert atmosphere |