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CAS No. : | 2605-68-7 | MDL No. : | MFCD08062441 |
Formula : | C22H21O2P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WCXPAYJKBTVUBC-UHFFFAOYSA-N |
M.W : | 348.38 | Pubchem ID : | 10569721 |
Synonyms : |
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.09 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 107.97 |
TPSA : | 36.11 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.61 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.96 |
Log Po/w (WLOGP) : | 3.35 |
Log Po/w (MLOGP) : | 4.73 |
Log Po/w (SILICOS-IT) : | 5.42 |
Consensus Log Po/w : | 3.49 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.7 |
Solubility : | 0.00699 mg/ml ; 0.0000201 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.42 |
Solubility : | 0.0133 mg/ml ; 0.0000381 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.02 |
Solubility : | 0.00000337 mg/ml ; 0.0000000097 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.97 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
91% | With potassium iodide In water; toluene at 70℃; for 20 h; | After dissolving 5 g (19.06 mmol) of triphenylphosphine in 15 ml of toluene, an aqueous solution of 0.32 g (1.90 mmol) of potassium iodide in 15 ml of distilled water and 3.2 ml (28.6 mmol) of methyl 2-bromopropionate were added thereto. And the mixture was stirred at 70 ° C for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, basified (pH 9) with 10 N aqueous sodium hydroxide solution, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, filtered under reduced pressure, and distilled under reduced pressure. The obtained solid was washed with hexane and then filtered under reduced pressure and dried under reduced pressure to give 6.0 g (yield: 91percent) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium iodide; In water; toluene; at 70℃; for 20h; | After dissolving 5 g (19.06 mmol) of triphenylphosphine in 15 ml of toluene, an aqueous solution of 0.32 g (1.90 mmol) of potassium iodide in 15 ml of distilled water and 3.2 ml (28.6 mmol) of <strong>[5445-17-0]methyl 2-bromopropionate</strong> were added thereto. And the mixture was stirred at 70 C for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, basified (pH 9) with 10 N aqueous sodium hydroxide solution, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, filtered under reduced pressure, and distilled under reduced pressure. The obtained solid was washed with hexane and then filtered under reduced pressure and dried under reduced pressure to give 6.0 g (yield: 91%) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In dichloromethane; water; at 20℃; for 0.25h;Inert atmosphere; | Sodium hydroxideaq. (2 M, 85 mL, 170mmol) was added to a solution ofcarbomethoxy methyl triphenylphosphonium bromide (5.15 g,12.0mmol) and CH2Cl2 (20 mL) at room temperature. Afterstirring for 15min at room temperature, the solution wasextracted with CHCl3 (2 15 mL), washed with brine (15 mL),dried over Na2SO4 and concentrated. The resulting ylide wasused without further purification. A solution of the ylide and CH2Cl2 (30 mL) was added to asolution of lactol 36 (1.00 g, 5.98mmol) and CH2Cl2 (30 mL) atroom temperature. After maintaining for 19 h at room temperature,diisopropylethylamine (5.2 mL, 30mmol) and BOMCl(3.3 mL, 24mmol) were added to the yellow solution at roomtemperature. The solution was maintained for 2 d at roomtemperature, quenched with H2O (40 mL) and extracted withCHCl3 (3 30 mL). The combined organic extracts werewashed with brine (30 mL), dried over Na2SO4 and concentrated.The residue was purified by silica gel column chromatography(EtOAc/hexane 1:24 to 1:7) to give 2.27 g of a mixtureof the unsaturated methylester 37 and benzyl alcohol, whichwas used in the next step without further purification. Foran analytical sample, the mixture was purified by HPLC(PEGASIL Silica 1205250 20 mm, UV 254 nm, EtOAc/hexane 1:3, 10mL/min, TR = 12min) to afford the pureunsaturated methylester 37 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In tetrahydrofuran; at 70℃; for 3h; | Preparation of polyene 43, (E)-9-phenyl-2,6-dimethyl-2,6-nonadienyl]-l-oxy-(feri'.- butyl)diphenyldimethyl-silane[0159] The synthesis route used in this example is shown schematically in Fig. 24 (see the appended figures). Hydrocinnamaldehyde (5.0 mmol, 1.0 eq, compound 81) in THF solution was subject to prop-l-en-2-ylmagnesium bromide (7.5 mmol, 1.5 eq) in THF solution at 0 C. The reaction was allowed to proceed 12 hours before quenching by pouring into water. The aqueous layer was extracted with dichloromethane (2 x 30 mL), and the <n="58"/>combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residual crude product was purified by column chromatography to afford the desired allylic alcohol product 82.[0160] The obtained 2-methyl-5-phenyl-l-penten-3-ol (5.0 mmol, 1.0 eq, compound 82) was subsequently mixed with triethyl orthoacetate (35.0 mmol, 7.0 eq) and catalytic amount of propionic acid (0.30 mmol, 0.06 eq) at room temperature. The mixture was refluxed at 150 0C for 12 hours, whereafter EtOH was distilled off from reaction mixture. The residual crude product was purified by column chromatography to afford the desired product ester 83. [0161] (E)-4-methyl-7-phenyl-4-heptenoic acid ethyl ester (compound 83, 2.0 mmol,1.0 eq.) was dissolved in toluene and cooled down to -78 C. Diisobutylaluminium hydride (DIBAL-H, 1.0 M in hexane, 3.0 mmol, 1.5 eq.) was added by means of a dry syringe. The reaction was allowed to proceed for 12 hours before quenching by adding MeOH at -78 C. A saturated aqueous solution of potassium sodium tartrate was added and warmed up to room temperature (rt). The aqueous layer was extracted with dichloromethane (2 x 30 mL), and the combined organic extracts were washed with water (30 mL) and brine (30 mL) and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residual crude product was purified by column chromatography to afford the desired product aldehyde 84.[0162] The obtained (4E)-4-methyl-7-phenyl-4-heptenal (compound 84, 2.0 mmol, 1.0 eq) was mixed together with ylide (6.0 mmol, 3.0eq) in THF. After refluxing for 4 hours, the solvent was removed in vacuo. The residual crude product was purified by column chromatography to afford (E)-2,6-dimethyl-9-phenyl-2,6-nonadienoic acid methyl ester (compound 85).[0163] Ester 85 (2.0 mmol, 1.0 eq) was dissolved in toluene and cooled down to -78 C. Diisobutylaluminium hydride (DIBAL-H5LO M in hexane, 4.0 mmol, 2.0 eq) was added by means of a dry syringe. The reaction was warmed upto room temperature and allowed to proceed for 12 hours before quenching by adding methanol at room temperature. Saturated potassium sodium tartrate aqueous solution was added and the mixture stirred for 1 hour. The aqueous layer was extracted with dichloromethane (2 x 30 mL), and the combined organic extracts were washed with water (30 mL) and brine (30 mL) and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residual crude product was purified by column chromatography to afford the desired product alcohol 86.[0164] (2E,6E)-2,6-dimethyl-9-phenyl-2,6-nonadien-l-ol (compound 86, 1.0 mmol, 1.0 eq ) was dissolved in THF together with imidazole (1.5 mmol, 1.5 eq) at room teperature. <n="59"/>(tert.-butyl)dimethyl-silylchloride (TBSCl, 1.2 mmol, 1.2 eq) was added. The reaction was allowed to proceed for 24 hours before quenching with water. The aqueous layer was extracted with dichloromethane (2 x 30 mL), and the combined organic extracts were washed with water (30 mL) and brine (30 mL) and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residual crude product was purified by column chromatography to afford (E)-9-phenyl-2,6-dimethyl-2,6-nonadienyl]-l-oxy-(fert.-butyl)dimethyl-silane (compound 43). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 150℃; for 48h; | EXAMPLE 58; A mixture of the commercially available ketone (1.64 g), methyl triphenylphosphoranylidene acetate (2.8 g), and 20 mL of toluene was heated at 150 0C for 2 days. The mixture was purified by Biotage (5% ethyl acetate in hexane) to afford the enoate (cis:trans=l:l) as a white solid. The hydrolysis of this enoate, and the subsequent amide formation, followed the procedures described in the Examples above to provide a yellow oil. A solution of the bromide (1.24 g), hexamethyl ditin (1.6 g) in 10 mL of THF was degassed with argon, and to this solution was added Pd(PPh3)4 (151 mg). The mixture was heated at 80 0C overnight. The resulting stannane mixture was used directly for the subsequent Stille coupling, following procedures described in the above Examples. Following similar procedures as described in EXAMPLE 54, after hydrogenation, conversion of the amino group to the hydroxyl group, and hydrolysis, the desired product was obtained as a brown oil. 1H NMR (acetone-d6, 500 MHz) δ 11.3 (IH, s), 8.75 (IH, d), 8.13 (IH, d), 8.10 (IH, d), 7.63 (IH, d), 7.60 (IH, t), 7.33 (IH, d), 7.25 (IH, dd), 7.16 (IH, t), 6.91 (IH, d), 3.68 (IH, m), 2.83 (IH, dd), 2.75 (IH, dd), 1.45 (3H, d); LCMS m/z 383 (M++l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In xylenes; at 170℃; for 4h;Heating / reflux; | EXAMPLE 7; To a xylenes solution of 6-methoxy-2-naphthaldehyde (0.855g, 4.585 mmol) was added the stabilized ylide shown in Scheme 2 (2.16g, 5.96 mmol, 1.3 eq.) at room temperature. The solution was heated to reflux for 4 h. The solvent was removed under vacuum, and the residue was chromatographed with AcOEt/Hexanes (4 to 1) to obtain the ethyl enoate intermediate. To a methanol solution of this intermediate (5.73 g) was added Pd/C (0-3 g), and the mixture was subjected to <n="33"/>hydrogenation under a balloon atmosphere of H2 gas, at room temperature for 16 h. The solution was filtered, and the solvent was removed in vacuo to obtain the saturated ester. The methoxy naphthyl ester (5.73 g) was treated with NCS (0.82g, 6.11 mmol, 1.1 eq) in DMF solvent at room temperature, and the solution was stirred for 16 h. Removal of the DMF in vacuo provided a residue which was recrystalized from methanol/methylene chloride to obtain the chlorinated intermediate. The racemic mixture of this chloride (1.5 g, 3.69 mmol) was separated into its single enantiomers using chiral HPLC with a Chiralcel OJ column, and isocratic elution with 35% isopropanol-heptane. The ethyl ester intermediate (65 mg, 0.21 mmol) was dissolved in (1:1) acetic acid-HCl (2 mL) and heated to 110 0C for 10 min. Then 5 mL of water was added, and the solution cooled to 0 0C to obtain the acid intermediate after filtration. Oxalyl chloride (0.3 mmol) was then added to a CH2CI2 (2 mL) solution of this acid intermediate (45 mg, 0.1 mmol), and one drop of DMF was added at 0 0C. The solvent was removed in vacuo after the solution was sirred for 1 h at room temperature. The residue was dissolved in THF (2 mL), and this solution was added to a THF (2 mL) solution of 3-amino-2-carboxylthiophene (0.11 mmol) and Et3N (0.3 mmol) at 0 0C. The pure thiophene methyl ester intermediate was obtained after HPLC purification. Potassium trimethylsilanolate (4 eq, 0.4 mmol) was added to a THF solution of this methyl ester intermediate (0.09 mmol) at 0 0C. The solution was stirred at room temperature for 2 h, and the desired product was obtained by preparative RPHPLC purification. 1H NMR (CD3OD, 500 MHz) delta 8.07 (d, IH), 7.99 (d, IH), 7.74 (d,lH), 7.66 (s, IH), 7.64(d, IH), 7.47 (dd IH), 7.40(d, IH), 4.00 (s, 3H), 3.17(m, IH), 2.97 (m, 2H), 1.30 (d, 3H); LCMS m/z 402 (M-I). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In dichloromethane; at 20℃; for 24h; | To a solution of lactol 18 (1.04 g, 4.29 mmol) in CH2Cl2 (10 mL, 0.43 M) was added <strong>[2605-68-7]methyl 2-(triphenylphosphoranylidene)propionate</strong> (4.48 g, 12.87 mmol) at room temperature. After being stirred at the same temperature for 24 h, the reaction mixture was diluted with a small amount of hexanes. This mixture was purified by column chromatography (silica gel, hexanes/ethyl acetate, 1:1) to give the mixture of α,β-unsaturated ester 19 as a colorless oil (1.26 g, E:Z = 95:5, total 94%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In dichloromethane; at 50℃; for 21h;Inert atmosphere; | A higher yielding alternative was the Wittig olefination with phosphorane 28:8.8 mg (28 μmol, 1.0 equiv) of olefin 12 were subjected to olefin cross metathesiswith crotonaldehyde and second generation Grubbs catalyst and purified asdescribed previously. The resulting unsaturated aldehyde 11 was solved in 2 mLCH2Cl2 and 11 mg (31 μmol, 1.1 equiv) of 26 were added. The resulting solution wasstirred at 50 C for 21 h. The solvent was removed under reduced pressure, and thecrude product was purified by flash chromatography on C18-reversed phase silica gel(MeCN/H2O 2:3). After drying in vacuo, 7.4 mg (18 μmol) of the colorless oil 10a wereobtained (64% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.7% | In toluene; at 90 - 100℃;Inert atmosphere; | 10103] Compound A- 1-1(2.0 g, 6.14 mmol), phosphonium ylide (3.21 g, 9.21 mmol) and methylbenzene 40 ml were charged successively into a 100 ml one-neck round-bottom flask. The mixture was heated to 90.-A 00 C. under nitrogen and maintained at this temperature. The reaction was monitored by TLC until all start raw materials were consumed. Afier the reaction was complete, the reaction mixture was concentrated under reduced pressure to give a residue which was then purified by column chromatography to afford 1.96 g the compound of formula A-2-i,with a molar yield of 80.7%. |
1.96 g | In toluene;Inert atmosphere; Heating; | Compound A-1-1(2.0g, 6.14mmol), phosphonium ylide(3.21g, 9.21mmol) and methylbenzene 40ml werecharged successively into a 100 ml one-neck round-bottom flask. The mixture was heated to 90~100C under nitrogenand maintained at this temperature. The reaction was monitored by TLC until all start raw materials were consumed.After the reaction was complete, the reaction mixture was concentrated under reduced pressure to give a residue whichwas then purified by column chromatography to afford 1.96g the compound of formula A-2-1, with a molar yield of 80.7% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In dichloromethane; at 0 - 20℃; for 13h;Inert atmosphere; | Sodium hydroxide aq. (1 M, 6.9 mL, 6.9 mmol) was added to a solution of carbomethoxy methyltriphenylphosphonium bromide (1.72 g, 4.01 mmol) and CH2Cl2 (10 mL) at room temperature. After stirringfor 20 min at room temperature, the solution was extracted with CH2Cl2 (2x 10 mL), washed with saturatedaqueous NH4Cl (10 mL) and brine (10 mL), dried over Na2SO4 and concentrated. The resulting ylide was usedwithout further purification.A solution of the ylide and CH2Cl2 (10 mL) was added to a solution of aldehyde 492 (504 mg, 2.68 mmol)and CH2Cl2 (17 mL) at 0 C. The solution was allowed to warm to room temperature, stirred at room temperaturefor 13 h, and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane 1:40)to give 519 mg of 50 (75%): a colorless oil; []26D 0.1 (c 1.07, CHCl3); IR (film) 2955, 2931, 2891, 2858,1721, 1253, 1072, 833 cm1; 1H NMR (500 MHz, CDCl3) 6.68 (dq, J = 8.0, 1.2 Hz, 1H), 4.61 (dq, J = 8.0, 6.6Hz, 1H), 3.74 (s, 3H), 1.83 (d, J = 1.2 Hz, 3H), 1.22 (d, J = 6.6 Hz, 3H), 0.88 (s, 9H), 0.05 (s, 3H), 0.03 (s, 3H);13C NMR (125 MHz, CDCl3) 168.8 (C), 146.2 (CH), 125.3 (C), 66.0 (CH), 52.0 (CH3), 26.0 (CH3), 23.5 (CH3),18.3 (C), 12.7 (CH3), 4.5 (CH3), 4.6 (CH3); HRMS (ESI), calcd for C13H26O3NaSi+ (M+Na)+ 281.1549, found281.1557. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
537 mg | In dichloromethane; at 20℃; for 17h;Inert atmosphere; | Oxalyl chloride (544 L, 6.24 mmol) was added dropwise to a solution of DMSO (664 L, 9.36 mmol) andCH2Cl2 (16 mL) at -78 C. The resulting solution was maintained for 30 min at -78 C. A solution of alcoholS12676 (429 mg, 2.08 mmol) and CH2Cl2 (5.0 mL) was then added dropwise via cannula at -78 C. After thesolution was maintained at -78 C for 1 h, Et3N (1.7 mL, 13 mmol) was added dropwise to the solution. Theresulting mixture was stirred at -78 C for 1 h, allowed to warm to room temperature, stirred for 10 min,quenched with H2O (10 mL), and extracted with EtOAc (7x 10 mL). The combined organic extracts werewashed with brine (50 mL), dried over Na2SO4, and concentrated to give the corresponding aldehyde 68 as ayellow oil, which was immediately used in the next reaction without further purification.Sodium hydroxide aq. (1 M, 8.0 mL, 8.0 mmol) was added to a solution of carbomethoxy methyltriphenylphosphonium bromide (1.34 g, 3.12 mmol) and CH2Cl2 (10 mL) at room temperature. After stirringfor 15 min at room temperature, the solution was extracted with CH2Cl2 (2x 10 mL), washed with brine (15mL), dried over Na2SO4 and concentrated. The resulting ylide was used without further purification.A solution of the ylide and CH2Cl2 (11 mL) was added to a solution of aldehyde 68 and CH2Cl2 (10 mL)at room temperature. The solution was stirred at room temperature for 17 h, and concentrated. The residue waspurified by silica gel column chromatography (EtOAc/hexane 1:9) to give 537 mg of unsaturated ester 69 (91%,2 steps): a colorless oil; []25D -28.7 (c 1.05, CHCl3); IR (film) 2936, 1720, 1254, 1238, 1152, 1041 cm-1; 1HNMR (500 MHz, CDCl3) 6.66 (dd, J = 8.6, 1.2 Hz, 1H), 4.65 (dd, J = 8.6, 8.6 Hz, 1H), 4.65 (s, 2H), 3.96 (ddd,J = 8.6, 5.5, 3.2 Hz, 1H), 3.75 (s, 3H), 3.67 (dd, J = 10.9, 3.2 Hz, 1H), 3.58 (dd, J = 10.9, 5.5 Hz, 1H), 3.36 (s,3H), 1.92 (d, J = 1.2 Hz, 3H), 1.45 (s, 6H); 13C NMR (125 MHz, CDCl3) 167.9 (C), 137.2 (CH), 132.2 (C),110.3 (C), 96.9 (CH2), 79.9 (CH), 74.3 (CH), 66.6 (CH2), 55.6 (CH3), 52.2 (CH3), 27.10 (CH3), 27.07 (CH3),13.2 (CH3); HMRS (ESI) calcd for C13H22O6Na (M+Na)+ 297.1314, found 297.1312. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 100℃; | A mixture of methyl 2-(triphenylphosphoranylidene)propanoate (2.5 g, 7.18 mmol) and cyclohexane-1,4-dione (1.609 g, 14.35 mmol) in toluene (25 mL) was stirred at 100 C. overnight and then concentrated in vacuo. The residue was triturated with a mixture of hexanes (100 mL) and ethyl acetate (100 mL), and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on Analogix IntelliFlash280 eluting with 0 to 50% ethyl acetate/hexanes to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.85 (p, J=1.5 Hz, 3H), 2.27-2.35 (m, 2H), 2.41 (dd, J=8.0, 5.8 Hz, 2H), 2.55-2.65 (m, 2H), 2.81-2.90 (m, 2H), 3.66 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In dichloromethane; at 0 - 25℃; for 12h; | To a mixture of (2R, 3S) -tert-butyl 3-formyl-2-methylmorpholine-4-carboxylate (2.29 g, 10 mmol) and DCM (100 mL) was added methyl 2- (triphenylphoranylidene) propanoate (3.48 g, 10 mmol) at 0 . The mixture was stirred at 25 for 12 hours, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) 1/16) ) to give the title compound as colourless oil (1.59 g, 53) . The compound was characterized by the following spectroscopic data: [0413] MS (ESI, Pos. ion) m/z: 200.1 [M+H-100] +. |
53% | In dichloromethane; at 0 - 25℃; for 12h; | (2R,3S)-3-Formyl-2-methylmorpholine-4-carboxylic acid tert-butyl ester (2.29 g, 10 mmol) was dissolved in DCM(100 mL), methyl 2-(triphenylphosphino)propanoate (3.48 g, 10 mmol) was added at 0 C.Reaction at 25 C for 12 hours, concentration reactionThe residue was purified by column chromatography (Et0Ac/PE (ν/ν) =1/16)Obtained a colorless oil(1.59g, 53%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In tetrahydrofuran; at 60℃; for 16h; | 130 mg (0.49 mmol) of the compound obtained in the above step 3) was diluted in 10 ml of tetrahydrofuran, 1.03 g (2.96 mmol) of the compound obtained in Example 1) was added, and the mixture was stirred at 60 C for 14 hours. After completion of the reaction, the residue obtained by distillation under reduced pressure was separated by column chromatography (dichloromethane: methanol = 20: 1, volume ratio) to give 180 mg (yield: 90%) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With lithium hydroxide; In tetrahydrofuran; for 10h;Reflux; | After 5.0 g (14.3 mmol) of the compound prepared in the above step 1) was dissolved in 40 ml of tetrahydrofuran, 0.6 g (4.78 mmol) of benzene-1,4-dicarbaldehyde was added and the mixture was refluxed with stirring at 60 C for 10 hours . After completion of the reaction, the reaction mixture was cooled to room temperature, and the residue obtained by distillation under reduced pressure was separated by column chromatography (hexane: ethyl acetate = 3: 1, volume ratio) to obtain 1.1 g of the title compound (yield: 83% . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In tetrahydrofuran; for 7h;Reflux; | Methyl (triphenylphosphoranylidene) propionate 21 (10.00g, 28.7mmol) was added to a solution of dodecyl aldehyde 22 (4mL, 18.1mmol) in THF (50mL) stirred at ambient temperature. Stirring was then continued for 7hat reflux temperature (when TLC showed completion of the reaction). The solvent was removed under reduced pressure. Et2O (20mL) was added. The solids were filtered off. The filtrate was concentrated by rotary evaporation. The residue was purified by flash chromatography (20:1 n-hexane/EtOAc) on silica gel to afford 23 as light yellow oil (4.4g, 17.4mmol, 96%, (E)/(Z)=97:3): 1H NMR (400MHz, CDCl3): δ 6.76 (tq, J=7.5, 1.3Hz, 1H), 3.73 (s, 3H), 2.16 (q, J=7.5Hz, 2H), 1.82 (s, 3H), 1.42 (quint, J=7.1Hz, 2H), 1.35-1.20 (m, 16H), 0.88 (t, J=6.9Hz, 3H); 13C NMR (100MHz, CDCl3): δ 168.7, 142.8, 127.3, 51.6, 31.9, 29.61, 29.59, 29.5, 29.4, 29.33, 29.30, 28.6, 28.5, 22.7, 14.1, 12.3; FT-IR (film): 2925, 2854, 1718, 1651, 1464, 1435, 1263, 1192, 1139, 1103cm-1. ESI-MS: m/z 255.4 ([M+H]+); ESI-HRMS calcd for C16H31O2 ([M+H]+): 255.2319, found 255.2315. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With manganese(IV) oxide; In dichloromethane; at 20℃; for 72h; | A mixture of 0.47 mL of propane-1,3-diol (0.5 g,6.57 mmol) and 5.0 g of the ylene Methyl-2-(triphenylphosphoranyliden)propanoate [54] was dissolvedin 17 mL of dichloromethane and 10.4 g of activated MnO2 were added. The mixture was stirredfor 3 days at r.t. and filtered. The solid residue was washed with methylene chloride and, aftersolvent evaporation, purified by column chromatography (hexane/EtOAc 1:4, Rf = 0.52) to give 447 mg (3.10 mmol, 47%) 12 as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ = 1.81 (s, 3H), 2.40 (q, J = 6.7 Hz,2H), 3.68 (m, 5H), 6.74 (t, J = 7.3 Hz, 1H); 13C-NMR (75 MHz, CDCl3): δ = 12.6 (q), 32.1 (t), 51.9 (q), 61.2 (t), 129.6 (s), 138.7 (d), 168.6 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Ozone in oxygen was bubbled through the solution of the alkene (1g, 6.65 mmol) inCH2Cl2 (20 mL) at -78 C. The reaction was monitored by TLC. When the starting material was consumed, the mixture was flushed with O2 for 10 min. After warming toroom temperature, the ylide (2.32g, 6.65 mmol ) was added and the mixture was heated atreflux for 4 hr. The reaction was cooled down to room temperature, and the solvent wasremoved under reduced pressure. The residue was taken up in the minimum amount ofCH2Cl2, and excess hexane was added. The precipitate was removed by filtration throughcelite, the filtrate was concentrated in vaccuo and purified via column chromatography. methyl (E)-2,6-dimethylnon-2-en-8-ynoate (2)Overall yield: 77%. Colorless oil.1H NMR (400 MHz, CDCl3) δ 6.75 (t, J= 7.3 Hz, 1H), 2.20-2.14 (m, 4H), 1.96 (s, 1H),1.84 (s, 3H), 1.72-1.60 (m, 3H), 1.00 (d, J= 6.4 Hz, 3H)13C NMR (100 MHz, CDCl3) δ 168.8, 142.4, 127.9, 83.0, 69.7, 51.9, 34.7, 32.2, 26.4,25.8, 19.5, 12.6.IR(neat) cm-1 : 3302, 2114, 1713, 1651, 1381, 1265, 1096, 934, 818, 741, 633.HRMS: (EI) Calcd. C12H19O2 (M+H)+ For 195.1385, Found: 195.1383; MS: (ESI) 217.99(M+Na)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In dichloromethane; at 20℃; for 2h;Inert atmosphere; | A solution of substrate 5 (2.3 g, 6.6 mmol) and 4 (1.3 g, 5.3 mmol) in 25 ml CH2Cl2was stirred for 2 h at room temperature. Then the solvents were removed underreduced pressure and the crude product was purified by flash column chromatographyto afford 6 (pure compound 1.6 g, 96%) as a light yellow liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Sodium hydroxideaq. (2 M, 85 mL, 170mmol) was added to a solution ofcarbomethoxy methyl triphenylphosphonium bromide (5.15 g,12.0mmol) and CH2Cl2 (20 mL) at room temperature. Afterstirring for 15min at room temperature, the solution wasextracted with CHCl3 (2 15 mL), washed with brine (15 mL),dried over Na2SO4 and concentrated. The resulting ylide wasused without further purification.A solution of the ylide and CH2Cl2 (30 mL) was added to asolution of lactol 36 (1.00 g, 5.98mmol) and CH2Cl2 (30 mL) atroom temperature. After maintaining for 19 h at room temperature,diisopropylethylamine (5.2 mL, 30mmol) and BOMCl(3.3 mL, 24mmol) were added to the yellow solution at roomtemperature. The solution was maintained for 2 d at roomtemperature, quenched with H2O (40 mL) and extracted withCHCl3 (3 30 mL). The combined organic extracts werewashed with brine (30 mL), dried over Na2SO4 and concentrated.The residue was purified by silica gel column chromatography(EtOAc/hexane 1:24 to 1:7) to give 2.27 g of a mixtureof the unsaturated methylester 37 and benzyl alcohol, whichwas used in the next step without further purification. Foran analytical sample, the mixture was purified by HPLC(PEGASIL Silica 1205250 20 mm, UV 254 nm, EtOAc/hexane 1:3, 10mL/min, TR = 12min) to afford the pureunsaturated methylester 37: a colorless oil; [α]24D 6.5 (c 1.06,CHCl3); IR (film) 2988, 2936, 2885, 1719, 1248, 1048, 1028cm1; 1HNMR (500 MHz, CDCl3) δ 7.367.27(m, 5H), 6.69(dq, J = 8.9, 1.7 Hz, 1H), 4.98 (dd, J = 8.9, 6.6 Hz, 1H), 4.77(d, J = 8.1 Hz, 1H), 4.75 (d, J = 8.1 Hz, 1H), 4.60 (d, J = 14.9Hz, 1H), 4.58 (d, J = 14.9 Hz, 1H), 4.42 (ddd, J = 7.5, 6.6,4.6 Hz, 1H), 3.72 (s, 3H), 3.57 (dd, J = 10.6, 7.5 Hz, 1H), 3.51(dd, J = 10.6, 4.6 Hz, 1H), 1.90 (d, J = 1.7 Hz, 3H), 1.53(s, 3H), 1.41 (s, 3H); 13CNMR (125 MHz, CDCl3) δ 167.7 (C),137.8 (C), 136.4 (CH), 131.0 (C), 128.6 (CH), 128.0 (CH),127.9 (CH), 109.7 (C), 95.1 (CH2), 77.2 (CH), 73.9 (CH),69.7 (CH2), 67.2 (CH2), 52.2 (CH3), 28.0 (CH3), 25.5 (CH3),13.2 (CH3); HMRS (ESI) calcd for C19H26O6Na+ (M + Na)+373.1627, found 373.1618. A mixture of unsaturated methylester 37 (2.27 g) was dissolvedin AcOH/H2O (4:1, 20 mL) at room temperature. Thissolution was warmed to 40 C, and stirred for 1 d at 40 C. Thesolution was cooled to room temperature, and concentrated.Acetic acid and H2O were azeotropically removed from EtOH(4 40 mL) and toluene (20 mL) under reduced pressure. Theresidue was purified by silica gel column chromatography(EtOAc/hexane 3:1) to give 1.62 g of allylic vicinal diol 38(87%, 2 steps): a colorless oil; [α]27D +9.6 (c 1.16, CHCl3); IR(film) 3435, 2951, 2886, 1715, 1245, 1122, 1042, 750 cm1;1HNMR (500 MHz, CDCl3) δ 7.397.28(m, 5H), 6.71 (dd,J = 8.6, 1.5 Hz, 1H), 4.79 (d, J = 8.9 Hz, 1H), 4.78 (d, J = 8.9Hz, 1H), 4.64 (d, J = 12.1 Hz, 1H), 4.61 (d, J = 12.1 Hz, 1H),4.57 (ddd, J = 8.6, 5.2, 5.2 Hz, 1H), 3.82 (dddd, J = 6.3, 5.2,4.6, 3.8 Hz, 1H), 3.74 (s, 3H), 3.72 (dd, J = 10.6, 3.8 Hz, 1H),3.70 (dd, J = 10.6, 6.3 Hz, 1H), 3.02 (d, J = 4.6 Hz, 1H), 2.67(d, J = 5.2 Hz, 1H), 1.90 (d, J = 1.5 Hz, 3H); 13CNMR (125MHz, CDCl3) δ 168.1 (C), 138.7 (CH), 137.5 (C), 130.8 (C),128.6 (CH), 128.1 (CH), 128.0 (CH), 95.5 (CH2), 72.5 (CH),70.1 (CH2), 69.9 (CH), 69.7 (CH2), 52.2 (CH3), 13.3 (CH3);HMRS (ESI) calcd for C16H22O6Na+ (M + Na)+ 333.1314,found 333.1313. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Sodium hydroxideaq. (2 M, 85 mL, 170mmol) was added to a solution ofcarbomethoxy methyl triphenylphosphonium bromide (5.15 g,12.0mmol) and CH2Cl2 (20 mL) at room temperature. Afterstirring for 15min at room temperature, the solution wasextracted with CHCl3 (2 15 mL), washed with brine (15 mL),dried over Na2SO4 and concentrated. The resulting ylide wasused without further purification.A solution of the ylide and CH2Cl2 (30 mL) was added to asolution of lactol 36 (1.00 g, 5.98mmol) and CH2Cl2 (30 mL) atroom temperature. After maintaining for 19 h at room temperature,diisopropylethylamine (5.2 mL, 30mmol) and BOMCl(3.3 mL, 24mmol) were added to the yellow solution at roomtemperature. The solution was maintained for 2 d at roomtemperature, quenched with H2O (40 mL) and extracted withCHCl3 (3 30 mL). The combined organic extracts werewashed with brine (30 mL), dried over Na2SO4 and concentrated.The residue was purified by silica gel column chromatography(EtOAc/hexane 1:24 to 1:7) to give 2.27 g of a mixtureof the unsaturated methylester 37 and benzyl alcohol, whichwas used in the next step without further purification. Foran analytical sample, the mixture was purified by HPLC(PEGASIL Silica 1205250 20 mm, UV 254 nm, EtOAc/hexane 1:3, 10mL/min, TR = 12min) to afford the pureunsaturated methylester 37: a colorless oil; [α]24D 6.5 (c 1.06,CHCl3); IR (film) 2988, 2936, 2885, 1719, 1248, 1048, 1028cm1; 1HNMR (500 MHz, CDCl3) δ 7.367.27(m, 5H), 6.69(dq, J = 8.9, 1.7 Hz, 1H), 4.98 (dd, J = 8.9, 6.6 Hz, 1H), 4.77(d, J = 8.1 Hz, 1H), 4.75 (d, J = 8.1 Hz, 1H), 4.60 (d, J = 14.9Hz, 1H), 4.58 (d, J = 14.9 Hz, 1H), 4.42 (ddd, J = 7.5, 6.6,4.6 Hz, 1H), 3.72 (s, 3H), 3.57 (dd, J = 10.6, 7.5 Hz, 1H), 3.51(dd, J = 10.6, 4.6 Hz, 1H), 1.90 (d, J = 1.7 Hz, 3H), 1.53(s, 3H), 1.41 (s, 3H); 13CNMR (125 MHz, CDCl3) δ 167.7 (C),137.8 (C), 136.4 (CH), 131.0 (C), 128.6 (CH), 128.0 (CH),127.9 (CH), 109.7 (C), 95.1 (CH2), 77.2 (CH), 73.9 (CH),69.7 (CH2), 67.2 (CH2), 52.2 (CH3), 28.0 (CH3), 25.5 (CH3),13.2 (CH3); HMRS (ESI) calcd for C19H26O6Na+ (M + Na)+373.1627, found 373.1618 |
Tags: 2605-68-7 synthesis path| 2605-68-7 SDS| 2605-68-7 COA| 2605-68-7 purity| 2605-68-7 application| 2605-68-7 NMR| 2605-68-7 COA| 2605-68-7 structure
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