ethyl (R_P,S)-hydroxy(phenyl)methane(P-phenyl)phosphinate | 918154-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (R_P,S)-hydroxy(phenyl)methane(P-phenyl)phosphinate
• 英文别名: ethyl hydroxy(phenyl)methyl(phenyl)phosphinate；ethyl (R(P)-S)-1-hydroxy(phenyl)methane(P-phenyl)phosphinate；(S)-[ethoxy(phenyl)phosphoryl]-phenylmethanol
• CAS: 918154-55-9
• 化学式: C₁₅H₁₇O₃P
• 分子量: 276.272
• InChiKey: ZSXYYFGHGVAOPG-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (R_P,S)-hydroxy(phenyl)methane(P-phenyl)phosphinate 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-((R)-ethoxy-phenyl-phosphinoyl)-phenyl-methyl ester
  参考文献：
  名称：

  An approach to the synthesis and assignment of the absolute configuration of all enantiomers of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate

  摘要：

  Ethyl butyryl oxy(phenyl)methane(P-phenyl)phosphinate was hydrolyzed using four bacterial species as biocatalysts. In all cases the reaction was stereoselective and isomers bearing an alpha-carbon atom with an (S)-configuration were hydrolyzed preferentially. Also a lack of stereo selectivity toward the phosphorus atom was observed. Hydrolysis of one enantiomeric mixture, namely mixture of (S-p,R) and (R-p,S) configuration afforded enantiomerically pure ethyl (R-p,S)-hydrox (phenyl)methane(P-phenyl)phosphinate, configuration of which was established by X-ray crystallography. The observed H-1 and P-31 NMR chemical shifts of Mosher esters of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate were correlated with the configurations of both stereogenic centers of all four stereoisomers. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.021
• 作为产物：
  描述：

  ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate 在 phosphate buffer 、 Bacillus subtilis whole cells 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 41.0h， 生成 ethyl (R_P,S)-hydroxy(phenyl)methane(P-phenyl)phosphinate
  参考文献：
  名称：

  An approach to the synthesis and assignment of the absolute configuration of all enantiomers of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate

  摘要：

  Ethyl butyryl oxy(phenyl)methane(P-phenyl)phosphinate was hydrolyzed using four bacterial species as biocatalysts. In all cases the reaction was stereoselective and isomers bearing an alpha-carbon atom with an (S)-configuration were hydrolyzed preferentially. Also a lack of stereo selectivity toward the phosphorus atom was observed. Hydrolysis of one enantiomeric mixture, namely mixture of (S-p,R) and (R-p,S) configuration afforded enantiomerically pure ethyl (R-p,S)-hydrox (phenyl)methane(P-phenyl)phosphinate, configuration of which was established by X-ray crystallography. The observed H-1 and P-31 NMR chemical shifts of Mosher esters of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate were correlated with the configurations of both stereogenic centers of all four stereoisomers. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.021

文献信息

• The new way to synthesize ethyl 1-butyryloxy-1-phenylmethane(<i>P</i>-phenyl)phosphinate and whole-cell biocatalysis by <i>Escherichia coli</i> and <i>Pseudomonas fluorescens</i>
  作者：Paulina Majewska

  DOI：10.1080/10426507.2019.1599890

  日期：2019.11.2

  enantioselectivity of 25.8 for one pair of enantiomers. Better results were obtained when the biocatalytic reaction was carrying out for a longer period and the conversion degree reached 71%, the enantiomeric excess of unreacted substrate was >99% and enantioselectivity increased to 32.1. In all cases, isomers bearing α–carbon atom of S configuration were hydrolyzed preferentially. Graphical Abstract

  摘要 合成了一种新化合物1-羧基-1-羟基-1-苯基甲烷(P-苯基)次膦酸乙酯，并利用核磁共振谱描述了其非对映异构体的构型。用丁酰氯酰化得到意想不到的产物，丁酰氧基（苯基）甲烷（对苯基）次膦酸乙酯，然后使用两种细菌物种作为生物催化剂进行水解。由大肠杆菌细胞进行的生物催化水解取得了良好的结果，得到了对映体过量 84% 的光学活性产物，一对对映体的对映选择性为 25.8。生物催化反应时间越长，转化率达到71%，未反应底物对映体过量>99%，对映选择性提高到32.1，效果越好。在所有情况下，带有 S 构型的 α-碳原子的异构体被优先水解。图形概要
• An approach to the synthesis and assignment of the absolute configuration of all enantiomers of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate
  作者：Paulina Majewska、Paweł Kafarski、Barbara Lejczak、Iwona Bryndal、Tadeusz Lis

  DOI：10.1016/j.tetasy.2006.09.021

  日期：2006.10

  Ethyl butyryl oxy(phenyl)methane(P-phenyl)phosphinate was hydrolyzed using four bacterial species as biocatalysts. In all cases the reaction was stereoselective and isomers bearing an alpha-carbon atom with an (S)-configuration were hydrolyzed preferentially. Also a lack of stereo selectivity toward the phosphorus atom was observed. Hydrolysis of one enantiomeric mixture, namely mixture of (S-p,R) and (R-p,S) configuration afforded enantiomerically pure ethyl (R-p,S)-hydrox (phenyl)methane(P-phenyl)phosphinate, configuration of which was established by X-ray crystallography. The observed H-1 and P-31 NMR chemical shifts of Mosher esters of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate were correlated with the configurations of both stereogenic centers of all four stereoisomers. (c) 2006 Elsevier Ltd. All rights reserved.