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CAS No. : | 5764-85-2 | MDL No. : | MFCD00086891 |
Formula : | C11H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DVIBDQWVFHDBOP-UHFFFAOYSA-N |
M.W : | 194.23 | Pubchem ID : | 99818 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.08 |
TPSA : | 46.53 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) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 2.03 |
Log Po/w (XLOGP3) : | 1.26 |
Log Po/w (WLOGP) : | 1.35 |
Log Po/w (MLOGP) : | 1.7 |
Log Po/w (SILICOS-IT) : | 1.98 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.83 |
Solubility : | 2.91 mg/ml ; 0.015 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.84 |
Solubility : | 2.83 mg/ml ; 0.0146 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.76 |
Solubility : | 0.338 mg/ml ; 0.00174 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
10 g (62.5%) | With potassium hydroxide; In ethanol; water; | A. preparation of 3-Hydroxy-3-phenylpropanoic Acid Ethyl 3-hydroxy-3-phenylpropanoate (19 g, 0.1 mole) was refluxed in a solution of KOH (10 g, 0.2 mole) in ethanol for two hours. The solvent was removed in vacuo and the residue was dissolved in H2 O. The H2 O solution was extracted with ethyl ether, then acidified with 37% hydrochloric acid. The oily product was extracted out with chloroform and the chloroform was removed in vacuo to yield 10 g (62.5%). The residue was crystallized two times from a hexane/benzene mixture to give an analytical sample of 3 g, m.p. 89-91. Anal. Calcd. for C9 H10 O3: C, 65.06; H, 6.07. Found: C, 65.09; H, 6.13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; diisopropylamine; In hexanes; diethyl ether; at -78 - 20℃; for 1.16667h; | Example 11.53; Synthesis of trans-4-4-dimethyl-6-(phenyl)-2-(4-nitrophenoxy)-2-oxo-1,3,2-dioxaphosphorinane; Step A: To a solution of diisopropylamine (58.4 g, 577 mmol) in dry ether (500 mL) at -78 C. under nitrogen was added n-BuLi (215 mL, 2.5 M in hexane, 538 mmol) over 30 min. The reaction was stirred for 10 min before addition of ethyl acetate (55 mL, 558 mmol) over a period 30 min. Freshly distilled benzaldehyde (47 mL, 443 mmol) in ether (50 mL) was slowly added over 30 min and the mixture was allowed to warm to room temperature. The reaction was quenched with saturated ammonium chloride (150 mL) at 0 C. The organic layer was washed, dried (anhydrous Na2SO4) and concentrated to give the crude addition product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cobalt(II) chloride; In acetonitrile; for 8h;Reflux; | Synthesis of ethyl 3-acetoxy-3-phenylpropanoate rac-3 A mixture of the racemic ethyl 3-hydroxy-3-phenylpropanoate rac-2 (50 mmol), acetic anhydride (60 mmol, 9.5 g, 9.55 mL), and anhydrous cobalt(II) chloride (32.4 g, 250 mmol) in acetonitrile (100 mL) was refluxed for 8 h. After cooling to room temperature, the cobalt(II) chloride was filtered off. The filtrate was evaporated in vacuo and the crude product was purified by preparative vacuum-chromatography using dichloromethane as eluent to obtain rac-3 as a light colorless semisolid in 91% yield. The 1H and 13C NMR data were in accordance with those reported in the literature. 32 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium tetrahydroborate; In ethanol; at 20℃; for 2h; | Method B: Into the ethanolic solution of ethyl 3-oxo-3-phenylpropanoate(1, 4.8 g, 25 mmol in 50 mL solvent), NaBH4 (850 mg,25 mmol) was added portionwise at room temperature. After thecompletion of the reaction (checked by TLC, approx. 2 h) the pHwas adjusted to 6.5 with 5% HCl. The ethanol was evaporated in vacuoand the mixture was extracted with CH2Cl2 (3 200 mL). Thecombined organic layer was dried over anhydrous magnesium sulfateand evaporated in vacuo. The crude product was purified bypreparative vacuum-chromatography using dichloromethanemethanol(9:1, v/v) as eluent to yield rac-2 (87%) as a colorlesssemisolid. The 1H and 13C NMR data were in accordance with thosereported in the literature.32 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 10% 2: 78% | With potassium borohydride In ethanol at 40℃; for 4h; | |
1: 25% 2: 55% | With potassium borohydride; fipronilβ-cyclodextrin In ethanol at 40℃; for 4h; | |
1: 39 %Spectr. 2: 61 %Spectr. | With sodium tetrahydroborate In water at 20℃; for 1h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | A solution of ethyl 2-(trimethylsilyl)acetate, 1 (137muL, 0.75 mmol) and benzaldehyde 2a (51 muL, 0.50 mmol) in anhydrous THF (2.5 mL) wastreated with dried Bu4NOAc (15 mg, 0.05 mmol) under N2. The resulting solution was stirred atroom temperature for 1 h. Aqueous HCl (2 M, 10 mL) was added and stirred for 30 min. Theresidue was extracted with diethyl ether (15 mL x 3), organic layers combined, washed withbrine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silicagel chromatography eluting with cyclohexane/ethyl acetate (90:10) afforded 3a as a colorless oil(88 mg, 90%). | |
72% | General procedure: IPr (0.6 mg, 0.0015 mmol) was dissolved in 1.0 mL dry DMF and cooled to 0 C, then aldehyde (0.3 mmol) and alpha-trimethylsilylethylacetate (82.4 muL, 0.45 mmol) were loaded via syringe under N2. Subsequently the reaction solution was stirred at room temperature until full consumption of the starting aldehyde indicated by TLC, 3 mL 1 N HCl was added at this moment and the mixture was continuously stirred for 0.5 h, then the mixture was extracted by ethyl acetate (3×15 mL). The combined organic phase was washed with saturated sodium bicarbonate and H2O, dried by anhydrous Na2SO4, and concentrated under vacuum. The crude product was purified through flash column chromatography (silica gel, PE/EtOAc, 8:1-4:1) to give the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With vinyl acetate; subtilisin In di-isopropyl ether at 10 - 40℃; | ||
In hexane; isopropyl alcohol at 35℃; Resolution of racemate; | 36 1HNMR (400 MHz, CDCl3) δ 1.27 (t, J=2 Hz, 3H, CH3), 2.73 (m, 2H, CHH), 4.16 (m, 2H, CH2CH3), 5.12 (m, 1H, CHOH), 7.26-7.39 (m, 5H, aromatic H); HPLC (CHIRALCEL OD-H; solvent, hexane/2-propanol 99/1; flow rate, 1.0 ml/min; temperature, 35° C.; UV wavelength, 220 nm); tR of both optical isomers of ethyl 3-hydroxy-3-phenylpropionate, 34.2 minutes and 45.3 minutes. In the reaction, the optical isomer detected at 34.2 minutes was a main component, but R and S isomers were not identified. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 66% 2: 10% | With indium(III) chloride In dichloromethane at 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With immobilized Candida parapsilosis ATCC 7330 In ethanol; water at 25℃; for 6h; | |
57% | With immobilised Candida parapsilosis ATCC 7330 whole cells In ethanol; water at 25℃; for 6h; | |
Multi-step reaction with 2 steps 1: 6.5 h / Ambient temperature; lipase PS-30 from Pseudomonas sp. 2: 83 percent / KHCO3 / acetone / 36 h / Heating |
Multi-step reaction with 2 steps 1: sodium hydroxide; water / ethanol / 3 h / 20 °C 2: Novozym 435 / toluene / 40 °C / Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 2.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 3.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 4.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 5.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C 5.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C 6.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C 7.1: 99 percent / HCl / diethyl ether | ||
Multi-step reaction with 3 steps 1.1: 85 percent / lithium aluminum hydride / tetrahydrofuran / 2 h 2.1: 95 percent / Et3N / CH2Cl2 / 0 h / -10 °C 3.1: O2; (-)-sparteine; 3 Angstroem sieves / Pd(OAc)2 / toluene / 36 h / 80 °C / 760 Torr 3.2: H2O / tetrahydrofuran / 65 °C 3.3: PPh3; DEAD; HCl (g) / diethyl ether / -10 - 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Under nitrogen atmosphere, 30 ML of THF was added to 3.96 g (6.50 mmol, 0.65 equivalent (equivalent relative to a carbonyl compound as a starting raw material; the same, hereinafter)) of (BrZnCH2COOEt·THF)2.. Under argon atmosphere, a solution of 1.06 g (10 mmol) of benzaldehyde in 5 ML of THF was added dropwise while stirring at 0?5C. The mixture was stirred at 0?5C for 3 hours. 25 ML of 1N hydrochloric acid was added dropwise at 20C or lower, followed by dilution with 50 ML of ethyl acetate.. Then, the layers were separated.. The organic layer was washed successively with 10 ML (*2) of 1N hydrochloric acid, 20 ML of an aqueous saturated sodium chloride solution, 20 ML (*2) of an aqueous saturated sodium bicarbonate solution and 20 ML of an aqueous saturated sodium chloride solution.. After washing, the organic layer was dried with anhydrous magnesium sulfate.. Concentration under reduced pressure afforded 1.76 g of the desired product (yield 91%).1H NMR (CDCl3), (ppm): delta 1.27 (3H, t, J=7.1 Hz), 2.67-2.82 (2H, m), 3.26 (1H, d, J=3.4 Hz), 4.19 (2H, q, J=7.1 Hz), 5.14 (1H, quint, J=4.0 Hz), 7.27-7.40 (5H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium perborate tetrahydrate; at 20℃; for 4h; | General procedure: CS(at)Cu(OH)2 (6.7 mg, 5 mol% Cu loading) and L4 (2.4 mg, 6 mol%) were mixed in water (2 mL). The mixture was stirred for 1 h at room temperature, followed by successive addition of chalcone 1a (41.0 mg,0.2 mmol) and B2(pin)2 (60.9 mg, 0.24 mmol). After stirring for 12 h at room temperature, the reaction mixture was filtered and washed with THF (3 mL). Excess amount of NaBO3·4H2O (244 mg) was then added to filtrate and the mixture was stirred at room temperature for 4 h. The aqueous layer was extracted with EtOAc (20 mL) three times, and the combined organic layers were dried over anhydrous Na2SO4. After concentrated under reduced pressure, the crude mixture was purified by preparative TLC (nhexane/EtOAc = 4/1) to afford the desired product 3a (45.3 mg, quant.). |
79% | With sodium peroxoborate tetrahydrate; at 20℃; for 4h; | 15 mg of chitosan supported copper hydroxide catalyst (CS Cu (OH) 2) and ligand L4 (2.4 mg, 0.012 mmol, 6 mol%) were added to a 2.5 mL reaction tube, 2.0 mL of water was added, and the mixture was stirred at room temperature 1 hour. To the above system, the starting materials I-14 (35.2 mg, 0.2 mmol) and the boron ester (B2 (pin 2)) (60.9 mg, 2.4 mmol) were successively added successively. The whole reaction was stirred at room temperature for 12 hours to carry out the reaction. After completion of the reaction, the whole reaction system was filtered, washed with 3 mL of tetrahydrofuran, and sodium perborate tetrahydrate (244 mg, 0.8 mmol) was directly added to the residue, and the whole system was stirred at room temperature for 4 hours. To the above system, 3 mL of ethyl acetate was added and the mixture was extracted with ethyl acetate (3 x 10 mL). The organic phase was separated, dried over anhydrous Na2SO4, filtered and the solvent was removed by rotary evaporation. The residue was purified by column chromatography on ethyl acetate / petroleum ether mixed solvent = 3: 1 to give 30.7 mg of III-14 in 79% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Burkholderia cepacia lipase D at 23 - 24℃; for 20h; Neat (no solvent); Enzymatic reaction; | 4.4.1. Analytical scale kinetic resolution of rac-2a and rac-2e General procedure: One of the lipases (50 mg/mL) and an acyl donor (vinyl acetate or butanoate, 5 equiv) were added into a solution of substrate (rac-2a or rac-2e, 0.25 M) in an organic solvent (1 mL) or in neat vinyl acetate. The reaction mixture was shaken (300 rpm) at room temperature (23-24 °C). For HPLC or GC analysis, the samples taken from the reaction mixture (10 μL) were diluted to 500 μL with 2-propanol or TBME and filtered before injection |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With dmap; triethylamine; In dichloromethane; at 20℃; | General procedure: Method A. At first, Et3N (6.17 mmol, 624 mg, 860 muL), acetyl chloride (6.17 mmol, 485 mg, 440 muL), and DMAP (0.16 mmol, 20 mg) were added into a solution of racemic 2a-e (5.61 mmol) in dry CH2Cl2 (15 mL). The mixture was stirred at room temperature for 2-3 h and then quenched with water (15 mL). The isolated organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off by rotatory evaporation. The crude product was purified by vacuum-chromatography on silica gel using hexane-EtOAc (3:1, v/v) as eluent to give the product as a semisolid with 60-70% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Candida rugose type VII lipase In octane at 20℃; for 15h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Candida rugose type VII lipase In octane at 20℃; for 15h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Candida rugose type VII lipase In octane at 20℃; for 15h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49%; 46% | With Candida rugose type VII lipase; In octane; at 25℃;Molecular sieve; Enzymatic reaction; | General procedure: At first, CrL (AYS Amano, 1 g) and 4 A molecular sieves (100 mg) were added into a solution of the substrate (rac-1a-m, 2.5 mmol) in n-octane (100 mL) and the reaction was started by the addition of vinyl decanoate (10 mmol, 1.98 g, 2.23 mL). The reaction mixture was shaken (1350 rpm) at room temperature until the conversion slightly exceeded 50%. The enzyme was removed by filtration and the reaction mixture was concentrated by vacuum distillation. The crude products were separated by column chromatography on silica gel using n-hexane/EtOAc (different ratio, depending on the substrate) as eluent to give the enantiomerically enriched product (R)-2a-m and the residual alcohol (S)-1a-m as a semisolid. The yield and enantiomeric excess of the products are listed in Table 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72 % ee | With Pseudomonas cepacia lipase immobilized on gold nanoparticles In aq. phosphate buffer at 23℃; for 8h; Resolution of racemate; Enzymatic reaction; | Kinetic resolution General procedure: 10 mg of selected enzyme was incubated 45 min at 23 °C with 0.2 mL solution of 3.5 nm AuNPs, 0.1 mL solution of 20 nm AuNPs or 0.2 mL of water. Enzyme prepared in this way was added to 1 mL of PBS with 0.1 mmol of 3-hydroxy-3-phenylpropanoate. The mixture was shaking at 23 °C until conversion was about 50% (monitored with TLC). The mixture was extracted with diethyl ether and washed with saturated solution of sodium bicarbonate. Extract was dried with anhydrous magnesium sulfate, filtered and solvent was evaporated under reduced pressure. Recovered substrate was purified with column chromatography.(0013)In case of immobilized enzymes 0.3 mL of enzyme on AuNPs in PBS was added instead of 10 mg of enzyme incubated with AuNPs.(0014)Selected experiments were performed 5 times. Differences in conversion and enantiomeric excess were less than 5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With hydroxylamine hydrochloride; sodium methylate; In methanol; at 0℃; | General procedure: To a stirred solution of sodium methoxide (10mmol) and 6mmol of hydroxylamine hydrochloride at 0C is added an ester (9 or 10, 3mmol). The reaction is monitored by TLC, and upon completion the reaction mixture is brought to pH 7-8 with 1M hydrochloric acid. The resulted mixture is extracted thrice with AcOEt, and the combined organic layer washes with brine. After drying over MgSO4, removement of the solvent under reduced pressure give a slight yellow oil. Compound 6 is obtained after purification with column chromatography on silica gel, eluting with AcOEt-petroleum ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With (((CH3)2N)(CCHCHN)(C5H3))Fe(C5(C6H5)5); In tert-Amyl alcohol; at 0℃; for 24h;Resolution of racemate; | General procedure: Catalyst (-)-1 (3.3 mg, 0.005 mmol), beta-hydroxy ester 2a-i (0.25 mmol) and t-amyl alcohol (1.0 mL) were sequentially added to a vial. The vial was capped and stirred at room temperature to help dissolve the catalyst. The reaction mixture was cooled to 0 C, and then acetic anhydride (18 muL, 0.19 mmol) was added. After the appropriate amount of time, the reaction mixture was quenched by the addition of a large excess of methanol. The resulting solution was concentrated, and the unreactive alcohol, the acetate and the catalyst were separated by flash chromatography using increasing polarity mixtures of pentane/ethyl acetate as eluent. The enantiomeric excess of the unreactive alcohol and the acetate were determined by HPLC (Table 2). The chromatograms are attached in Supplementary section 2. Chemical shifts and literature NMR shifts were used as references in identification and characterization of the optically pure synthesized compounds 2a-i. The 1H and 13C{1H}-NMR spectra are attached in Supplementary section 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 32.4 % ee 2: 95.4 % ee | Stage #1: Ethyl 3-hydroxy-3-phenylpropanoate With (((CH3)2N)(CCHCHN)(C5H3))Fe(C5(C6H5)5) In tert-Amyl alcohol at 0℃; for 0.25h; Stage #2: acetic anhydride In tert-Amyl alcohol at 0℃; for 3h; Resolution of racemate; enantioselective reaction; | Selectivity Factor for the KR of 2a-i after 3 h Catalyst (-)-1 (2.0 mg, 0.003 mmol), β-hydroxy ester 2a-i (0.15 mmol) and t-amyl alcohol (0.6 mL) were sequentially added to a vial. The vial was capped and stirred at room temperature to help dissolve the catalyst. The reaction mixture was cooled to 0 °C in an ice-water bath and stirred for 15 min. Then, acetic anhydride (11 μL, 0.11 mmol) was added. After 3 h, a sample (0.2-0.3 mL) was quenched by the addition of methanol. The resulting solution was filtered through a short plug of silica using ether as eluent and then it was concentrated. The enantiomeric excess of the unreactive alcohol and the acetate were determined by HPLC (Table 1) using the appropriate chiral column and conditions. The chromatograms are attached in Supplementary section 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With bismuth(lll) trifluoromethanesulfonate; In dichloromethane; at 20℃; for 3h; | General procedure: Bi(OTf)3 (1.0 mol%) was added to a solution of the appropriate secbenzylalcohol (1.0 equiv) and TMSN3 (1.2 equiv) in CH2Cl2 (4.0mL/mmol) at r.t. When the reaction was complete (TLC), the solventwas removed and the crude material was purified by column chromatography. |
34% | With bismuth(lll) trifluoromethanesulfonate; In dichloromethane; at 20℃; for 3h; | General procedure: Bi(OTf)3 (1.0 mol%) was added to a solution of the appropriate secbenzylalcohol (1.0 equiv) and TMSN3 (1.2 equiv) in CH2Cl2 (4.0mL/mmol) at r.t. When the reaction was complete (TLC), the solventwas removed and the crude material was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 84 % ee 2: 66 % ee | With (R)-9-methyl-2-phenyl-9-hydro-2-imidazolino[1,2-a]benzimidazole In diethyl ether at 20℃; for 24h; Resolution of racemate; Inert atmosphere; | Typical procedure for the acylative kinetic resolution of racemic β-hydroxy ester (±)-9f(Table 2, entry 15): General procedure: To a solution of β-hydroxy ester (±)-9f (55.7 mg, 0.25 mmol) in Et2O (1.25 mL) were successively added (R)-N-methylbenzoguanidine ((R)-NMBG; 3) (3.2 mg, 12.8 μmol) and cyclohexanecarboxylic anhydride (8b) (46.2 μL, 0.19 mmol). The reaction mixture was stirred for 24 h at room temperature and then it was quenched with saturated aqueous NaHCO3 at 0 °C. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4. After filtration of the mixture and evaporation of the solvent, the crude product was purified preparative thin layer chromatography on silica (hexane/EtOAc = 4/1) to afford the corresponding optically active ether 11f (40.1 mg, 48%yield, 89% ee) and the recovered optically active alcohol 9f (24.0 mg, 43% yield, 91% ee) [s =54]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (R)-9-methyl-2-phenyl-9-hydro-2-imidazolino[1,2-a]benzimidazole; In diethyl ether; at 20℃; for 24h;Resolution of racemate; Inert atmosphere; | General procedure: To a solution of β-hydroxy ester (±)-9f (55.7 mg, 0.25 mmol) in Et2O (1.25 mL) were successively added (R)-N-methylbenzoguanidine ((R)-NMBG; 3) (3.2 mg, 12.8 μmol) and <strong>[22651-87-2]cyclohexanecarboxylic anhydride</strong> (8b) (46.2 μL, 0.19 mmol). The reaction mixture was stirred for 24 h at room temperature and then it was quenched with saturated aqueous NaHCO3 at 0 C. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4. After filtration of the mixture and evaporation of the solvent, the crude product was purified preparative thin layer chromatography on silica (hexane/EtOAc = 4/1) to afford the corresponding optically active ether 11f (40.1 mg, 48%yield, 89% ee) and the recovered optically active alcohol 9f (24.0 mg, 43% yield, 91% ee) [s =54]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 32 % ee 2: 57 % ee | With (R)-9-methyl-2-phenyl-9-hydro-2-imidazolino[1,2-a]benzimidazole In diethyl ether at 20℃; for 24h; Resolution of racemate; Inert atmosphere; | Typical procedure for the acylative kinetic resolution of racemic β-hydroxy ester (±)-9f(Table 2, entry 15): General procedure: To a solution of β-hydroxy ester (±)-9f (55.7 mg, 0.25 mmol) in Et2O (1.25 mL) were successively added (R)-N-methylbenzoguanidine ((R)-NMBG; 3) (3.2 mg, 12.8 μmol) and cyclohexanecarboxylic anhydride (8b) (46.2 μL, 0.19 mmol). The reaction mixture was stirred for 24 h at room temperature and then it was quenched with saturated aqueous NaHCO3 at 0 °C. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4. After filtration of the mixture and evaporation of the solvent, the crude product was purified preparative thin layer chromatography on silica (hexane/EtOAc = 4/1) to afford the corresponding optically active ether 11f (40.1 mg, 48%yield, 89% ee) and the recovered optically active alcohol 9f (24.0 mg, 43% yield, 91% ee) [s =54]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 44 % ee 2: 33 % ee | With (R)-9-methyl-2-phenyl-9-hydro-2-imidazolino[1,2-a]benzimidazole In diethyl ether at 20℃; for 24h; Resolution of racemate; Inert atmosphere; | Typical procedure for the acylative kinetic resolution of racemic β-hydroxy ester (±)-9f(Table 2, entry 15): General procedure: To a solution of β-hydroxy ester (±)-9f (55.7 mg, 0.25 mmol) in Et2O (1.25 mL) were successively added (R)-N-methylbenzoguanidine ((R)-NMBG; 3) (3.2 mg, 12.8 μmol) and cyclohexanecarboxylic anhydride (8b) (46.2 μL, 0.19 mmol). The reaction mixture was stirred for 24 h at room temperature and then it was quenched with saturated aqueous NaHCO3 at 0 °C. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4. After filtration of the mixture and evaporation of the solvent, the crude product was purified preparative thin layer chromatography on silica (hexane/EtOAc = 4/1) to afford the corresponding optically active ether 11f (40.1 mg, 48%yield, 89% ee) and the recovered optically active alcohol 9f (24.0 mg, 43% yield, 91% ee) [s =54]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 19 % ee 2: 69 % ee | With (R)-9-methyl-2-phenyl-9-hydro-2-imidazolino[1,2-a]benzimidazole In diethyl ether at 20℃; for 24h; Resolution of racemate; Inert atmosphere; | Typical procedure for the acylative kinetic resolution of racemic β-hydroxy ester (±)-9f(Table 2, entry 15): General procedure: To a solution of β-hydroxy ester (±)-9f (55.7 mg, 0.25 mmol) in Et2O (1.25 mL) were successively added (R)-N-methylbenzoguanidine ((R)-NMBG; 3) (3.2 mg, 12.8 μmol) and cyclohexanecarboxylic anhydride (8b) (46.2 μL, 0.19 mmol). The reaction mixture was stirred for 24 h at room temperature and then it was quenched with saturated aqueous NaHCO3 at 0 °C. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4. After filtration of the mixture and evaporation of the solvent, the crude product was purified preparative thin layer chromatography on silica (hexane/EtOAc = 4/1) to afford the corresponding optically active ether 11f (40.1 mg, 48%yield, 89% ee) and the recovered optically active alcohol 9f (24.0 mg, 43% yield, 91% ee) [s =54]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With toluene-4-sulfonic acid; In dichloromethane; at 20℃; for 16h; | General procedure: A mixture of the alcohol 1 (1 mmol), isopropenyl acetate (0.45 mL, 4 mmol) and p-TsOH (4 mg, 0.02 mmol) in dichloromethane or acetonitrile (4 mL) was stirred the indicated temperature (see Tables 1 and 2). Reaction times ranged from 16 to 36 h. After completion of the reaction (TLC monitoring) the mixture was poured into 10 mL of 10% aqueous sodium hydrogen carbonate solution. The aqueous phase was extracted with ethyl acetate (3 × 10 mL) and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate and then evaporated under vacuum. Purification by silica gel column chromatography afforded the pure acetyl ester 2. Physical and spectral data of known compounds were consistent with the ones reported in literature. Physical and spectral data of not previously described compounds are reported below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 1,1-dimethyl-3,3-diethylguanidinecarbonylcobalt; at 80℃; under 45004.5 Torr; for 24h;Autoclave; | General procedure: The reaction was conducted in a 50-mL stainless steel autoclave equipped with a stirring magnet. The reactor was charged with ethanol (3.0 mL), epoxide (5.0 mmol), and catalyst 3a (3 mol%). Then, the reactor was pressurized with 6.0 MPa CO and heated to 80 C. After completion of the reaction, the autoclave was cooled with ice water and slowly depressurized to atmospheric pressure. The product mixture underwent simple flash column chromatography to dispose of the ILs catalyst and was then analyzed using gas chromatography (GC) and GC-MS. |
40% | With 1,1-dimethyl-3,3-diethylguanidinecarbonylcobalt; at 80℃; under 45004.5 Torr; for 24h;Autoclave; Schlenk technique; | In an autoclave having a volume of 50 mL was added 3 mL of absolute ethanol, 5 mmol of styrene oxide, 3 mol% of cobalt carbonyl 1,1,3,3-tetraalkylguanidine Metal organic ionic liquid catalyst a.Airtight reactor, the reactor replaced with carbon monoxide 3 times, closed reactor.In the Schlenk vacuum line, the reaction system was replaced with carbon monoxide gas at room temperature three times, charged with CO gas pressure of 6.0 MPa, the temperature was slowly raised to 80 oC by a temperature control instrument, the reaction 24 hours,The mixture was cooled to room temperature, unloaded and the reaction mixture was subjected to column chromatography to obtain the target product Ethyl-3-Hydroxy-3-Phenyl Propionate, 0.39g, yield 40%. |
Tags: 5764-85-2 synthesis path| 5764-85-2 SDS| 5764-85-2 COA| 5764-85-2 purity| 5764-85-2 application| 5764-85-2 NMR| 5764-85-2 COA| 5764-85-2 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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