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CAS No. : | 25779-13-9 | MDL No. : | MFCD00066256 |
Formula : | C8H10O2 | Boiling Point : | - |
Linear Structure Formula : | C6H5CH(OH)CH2OH | InChI Key : | PWMWNFMRSKOCEY-MRVPVSSYSA-N |
M.W : | 138.16 | Pubchem ID : | 643312 |
Synonyms : |
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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 |
---|---|---|
95% | In the glove box, add the Mn-Cat.1 catalyst (3.8 mg, 0.005 mmol) and the substrate α-hydroxyacetophenone (136 mg, 1 mmol) into a 5 mL clear glass vial, then potassium carbonate (1.4 mg, 0.01 mmol) and absolute ethanol (3 mL) were added, and the mixture was stirred at room temperature for 5 min. Finally, the hydrogenation bottle was put into the autoclave, the hydrogen was replaced three times and then filled with 30 bar H2, and reacted at 50C for 16h. After the reaction is completed, the hydrogen is released carefully, the solvent is spin-dried under reduced pressure, and the hydrogenated product alcohol is purified by silica gel column, a colorless viscous liquid. The reaction is determined by HPLC, >99% conversion, 95% yield, 80% ee. | |
With hydrogen;dichloro[(R)-N-bis(3,4-difluorophenyl)phosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In ethanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material; | Complex 5A-j from Example 12 (2.8 mg; 0.0025 mmol; 0.005 equiv) and 2hydroxy-acetophenone (68 mg; 0.5 mmol) were placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed ethanol (5 mL) was added and the reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times. Analysis of the reaction mixture by chiral GC indicated 11.2% conversion to (R)-1-phenyl-1,2-ethanediol with 77.6% ee according to chiral GC. Chiral GC [30 m×0.25 mm Cyclosil-B (J&W Scientific), 0.25 μm film thickness, 150 C. isothermal]: tR=12.94 min (2-hydroxy-acetophenone), tR 28.30 min [(S)-1-phenyl-1,2-ethanediol], tR=29.21 min [(R)-1-phenyl-1,2-ethanediol]. | |
With formic acid; triethylamine;Cp*IrCl[(S,S)-MsDPEN]; at 50℃; for 24h;Product distribution / selectivity; | A formic acid-triethylamine mixture (molar ratio of HCOOH:Et3N:substrate=3.1:2.6:1) as the hydrogen source, 1.044 mg (1.6 μmol) of Cp*IrCl[(S,S)-MsDPEN] as the catalyst, and 1.089 g (8.0 mmol) of α-hydroxyphenone were introduced in a 20 mL Schlenk tube, and the mixture was subjected to argon substitution and maintained at 50 C. for 24 hr while stirring. HPLC analysis of the reactant confirmed that 1-phenyl-1,2-ethanediol with optical purity of 66% ee was produced in 12% yield. |
With potassium formate;(1,2,3,4,5-pentamethylcyclopentadienyl)IrCl[(S,S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]; In water; toluene; at 50℃; for 24h;Product distribution / selectivity; | The reaction was performed under the same conditions as those in Example B-1, except that 1.165 mg (1.6 μmol) of Cp*IrCl[(R,R)-TsDPEN] was used as the catalyst. HPLC analysis of the reactant confirmed that 1-phenyl-1,2-ethanediol with optical purity of 28% ee was produced in 30% yield. Comparison with Example B-1 demonstrated that it is superior to have a methyl group as the substituent on the sulfonyl group. | |
With potassium formate;[(1,2,3,4,5-pentamethylcyclopentadienyl)IrCl((S,S)-N-(p-toluenesulfonyl)-1,2-cyclohexanediamine(1-))]; In water; toluene; at 50℃; for 24h;Product distribution / selectivity; | The reaction was performed under the same conditions as those in Example B-1, except that 1.008 mg (1.6 μmol) of Cp*IrCl[(S,S)-TsCYDN] was used as the catalyst. HPLC analysis of the reactant confirmed that 1-phenyl-1,2-ethanediol with optical purity of 68% ee was produced in 10% yield. Comparison with Example B-1 demonstrated the superiority of MsDPEN as the dimaine ligand. | |
With potassium formate;Cp*IrCl[(R,R)-(R)-CsDPEN]; In water; toluene; at 50℃; for 24h;Product distribution / selectivity; | The reaction was performed under the same conditions as those in Example B-1, except that 1.467 mg (1.6 μmol) of Cp*IrCl[(R,R)-(R)-CsDPEN] was used as the catalyst. HPLC analysis of the reactant confirmed that 1-phenyl-1,2-ethanediol with optical purity of 87% ee was produced in 40% yield, showing that the catalytic efficiency of the iridium complex having camphorsulfonyl DPEN as the ligand is insufficient for the asymmetric reduction of ketones having a functional group. | |
With hydrogen;Ru(trifluoromethanesulfonate)(N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine)(η6-cymene); In methanol; at 50℃; under 76005.1 Torr; for 16h;Product distribution / selectivity; | The hydrogenation reaction of α-hydroxyacetophenone was performed by the same method as in Example 30 except that the sulfonate catalyst was changed to Ru(OTf)[(S,S)-Tsdpen](p-cymene). As a result, 67% ee of optically active 1-phenyl-1,2-ethanediol was produced in a yield of only 3%. | |
With potassium phosphate; Candida parapsilosis aldo-keto reductase CPAR5; NADPH; at 30℃; for 8h;pH 6.5;Enzymatic reaction; | General procedure: Asymmetric reductions of various carbonyl compounds by the purified enzymes were carried out at 30C for 8h with mild shaking in a reaction mixture containing 0.1M potassium phosphate buffer (pH 6.5), 1gL-1 substrate, 10mM NADPH, and the purified enzyme of appropriate amount in a total volume of 2mL. In order to determine the absolute configuration of chiral alcohols, the reaction products were extracted with ethyl acetate or hexane and the organic layer was used for analysis. The optical purity of the reaction products were determined by chiral HPLC (HP 1100, Agilent, USA) equipped with Chiralcel OB-H column (4.6mm×250mm; Daicel Chemical Ind. Ltd., Japan) or chiral GC (7890A, Agilent, USA) equipped with FID detector and Chrompack Chirasil-Dex CB chiral capillary column (25m×0.25mm; Varian, USA) [21]. | |
With silver tetrafluoroborate; diethoxymethylane; C26H29N3O2*Cl(1-)*Ir(1+)*C8H12; at 20℃; for 20h; | General procedure: A flask was charged with azolium salt L12 (0.02 mmol, 9.1 mg),Ag2O (0.01 mmol, 2.4 mg) and CH2Cl2(1 mL). After stirring the resulting mixture at room temperature for 2 h in the dark, CH2Cl2 was removed in vacuo. Then, a THF (1 mL) solution of [IrCl(cod)]2(0.01 mmol, 6.9 mg) was added to the reaction vessel. The resulting mixture was stirred at room temperature for an additional 4 h in the dark, filtered through a membrane filter, and evaporated to dry-ness in vacuo. Subsequently, to the resulting flask containing yellow solid of the unpurified IrCl(cod)(NHC) complex, a solution of AgBF4(0.025 mmol, 4.9 mg) in CPME (2 mL) was added, and then stirred at room temperature for 1 h. Finally, propiophenone (0.5 mmol,66 mg) and (EtO)2MeSiH (2.25 mmol, 294 mg) were added to the resulting CPME solution (see Appendix A. Supplementary data fordetails). After stirring at room temperature for 20 h under open-air conditions, K2CO3(2 mg) and MeOH (2 mL) were added. Then, the resulting mixture was stirred at room temperature for 2 h. Afterevaporation of the solvents, the residue obtained was purified bycolumn chromatography on silica gel (Et2O/n-hexane = 3:7) to give(S)-1-phenyl-1-propanol (61 mg, 91% isolated yield). The ee was measured by chiral GLC. | |
With C. parapsilosis strains containing exogenous gene scrII; In aq. phosphate buffer; at 35℃; for 45h;pH 6.0;Microbiological reaction; | methodsThe asymmetric reduction of 2-HAP to (S)-PED by C. parapsilosiswas conducted as described by Nie et al. [26] with some mod-ifications. After 36 h incubation, cells were collected at 6000 × gcentrifugation and washed twice with saline. For asymmetric reac-tion, 1 mL of the reaction mixture contained 0.2 M acetate (pH4.0-6.0) or 0.2 M phosphate buffer (pH 6.0-7.0), 2-HAP (1 g/L to30 g/L) and 10% (W/V) wet-cells of C. parapsilosis. The productswere extracted with ethyl acetate, and the optical purity andyield were determined by HPLC on a Chiralcel OB-H column (Dai-cel Chemical Ind, Ltd., Japan) as described previously [26]. Theoptical purity and yield were calculated basing on the followingequations | |
The N. corallina cells were incubated in 50 mL phosphate buffer (0.1 mol L-1, pH 7.00),30 min, at 28-30 C in an orbital shaker (150 rpm), and 2a or 2b was added to the whole cellsat a substrate:cells mass ratio of 1:100 for 2a and 1:400 for 2b, using 0.6 vol. % of N,N--dimethylformamide and shaken under the same conditions. The experiments were performedin triplicate at different final pH values of the culture media and times. The sample was centrifugedat 4500 rpm for 15 min and then extracted with ethyl acetate (4×15 mL), and the organiclayer was concentrated to dryness. The product was dissolved in 0.5 mL of HPLC grade2-propanol. The GC analysis was performed with a HP-5 column (30 m×0.33 mm, 0.25 μm)(Hewlett-Packard, Germany) at 80-200 C, with N2 as the carrier gas at 1.0 mL min-1. Theoven temperature was ramped from 80-200 C at 10 C min-1, held for 3 min, decreased to 80C at 25 C min-1 and held for 2 min. The retention times were tR(2a) = 4.90 min and tR(2b) == 5.79 min. Then, the analyse was realized by HPLC using a chiracel OB-H (25.0 cm×0.46cm, 0.5 μm) column (Daicel Chemical Industries, Tokyo, Japan). The mobile phase washexane:2-propanol (90:10), 0.5 mL min-1, λ = 220 nm, 24 C. For the reduction of 2a, theretention times were tR(R)-2b = 15.10 min, tR(S)-2b= 18.90 min and tR(2a) = 28.90 min. Forthe oxidation of 2b, the mobile phase was hexane:2-propanol (90:10), 0.8 mL min-1, λ = 260nm, 24 C. The retention times were tR(R)-2b = 9.04 min, tR(S)-2b = 11.38 min and tR(2a) == 17.12 min, The absolute configuration of 2b was assigned according to the literature.23 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In methanol; at 20℃; for 4h; | General procedure: In order to determine the enantiomeric excesses in the cases of styrene derivatives as starting materials, the pure product was dissolved in MeOH (0.1 M). Addition of K2CO3 (1.5 equiv) was followed by stirring at r.t. for 4 h. MeOH was removed under reduced pressure after acidification with aq 1 M HCl. Extraction of the aqueous layer with CH2Cl2 (3 ×), drying the combined organic layers over Na2SO4, and evaporation of the solvent yielded the corresponding diol, which was submitted to HPLC analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With Aspergillus niger epoxide hydrolases; In aq. phosphate buffer; dimethyl sulfoxide; at 25℃; for 4h;pH 7.0;Enzymatic reaction;Kinetics; | General procedure: Asymmetric hydrolysis of (R/S)-SO, (R/S)-PO and (R/S)-ECH were examined in a batch type reactor (1.1 cm × 5 cm). To 1.5 mL of 100 mM phosphate buffer (pH = 7.0 for the free and EHIL; pH = 6.5 for EHIF and EHIE), 100 L of the free EH solution (1 mg mL-1) or 30 mg of each immobilized EH was loaded and the mixture kept at 25 C for 2 min. The reaction was initiated by the addition 0.4 mL of each racemic epoxide solution (0.5 M in DMSO). A hundred microliters of aliquots withdrawn at different time intervals (15, 30,60, 90, 120, 180 and 240 min) were mixed with 400 L of diethylether and analyzed by a Shodex ORpak CDC-453 HQ chiral HPLC column (4.6 mm × 150 mm) according to Yildirim et al. [23]. The enantiomers of styrene oxide and their vicinal diols were detected at 220 nm. The enantiomers of propylene oxide, epichlorohydrin and their vicinal diols were detected using a refractive index detector (Shimadzu RID-10A). The optical configurations of remaining epoxides and formed diols were identified by comparing the retention time of these compounds with their optically active standard forms. The enantiomeric excess (ee) values of formed vicinal diol and remaining epoxide were calculated from the equations: eeepoxide=([S-R]epoxide)/([S+R]epoxide) and eediol=([R-S]diol)/([R+S]diol) The enantiomeric ratio values (E) of free and immobilized EHs were calculated from the equation proposed by Chen et al. [27]. E=(Vmax(R)/Km(R))/(Vmax(S)/Km(S)) where Vmax(R) and Km(R) values are maximum velocity and Michealis-Menten constant of free and immobilized EH preparations toward (R)-enantiomer of epoxide and Vmax(S) and Km(S) are corresponding values toward (S)-enantiomer of epoxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; isopropyl alcohol; at 35℃;Resolution of racemate;Product distribution / selectivity; | 1HNMR (400 MHz, CD3COCD3) δ 3.53 (dd, J=2 Hz, 4 Hz, 1H, CHHOH), 3.64 (dd, J=2 Hz, 10 Hz, 1H, CHHOH), 4.04 (br, H, OH), 4.43 (br, 1H, OH), 4.73 (dd, J=4 Hz, 10 Hz, 1H, CHOH), 7.21-7.40 (m, 5H, aromatic H); HPLC (CHIRALCEL OB; solvent, hexane/2-propanol=98/2; flow rate, 1.0 ml/min; temperature, 35 C.; UV wavelength, 220 nm); tR of both optical isomers of 1-phenyl-1,2-ethanediol, 26.0 minutes and 36.2 minutes. In the reaction, the optical isomer detected at 26.0 minutes was a main component, but R and S isomers were not identified. |
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