ethyl hydroxy(phenyl)methyl(phenyl)phosphinate | 1019777-12-8

• 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 hydroxy(phenyl)methyl(phenyl)phosphinate
• 英文别名: ethyl (R(P),R)-1-hydroxy(phenyl)methane(P-phenyl)phosphinate；(R)-[ethoxy(phenyl)phosphoryl]-phenylmethanol
• CAS: 1019777-12-8
• 化学式: C₁₅H₁₇O₃P
• 分子量: 276.272
• InChiKey: ZSXYYFGHGVAOPG-BEFAXECRSA-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

• 作为产物：
  描述：

  ethyl 1-butyryloxy-1-phenylmethane(P-phenyl)phosphinate 在 Candida cylinracea lipase 、 水 、 lithium chloride 作用下， 以 异丙醚 为溶剂， 反应 48.0h， 生成 ethyl (S_P,S)-hydroxy(phenyl)methane(P-phenyl)phosphinate 、 ethyl (R_P,R)-butyryloxy(phenyl)methane(P-phenyl)phosphinate 、 ethyl hydroxy(phenyl)methyl(phenyl)phosphinate
  参考文献：
  名称：

  Enzymatic Resolution of Ethyl α-Hydroxyphosphinates in a Modified Reaction Environment

  摘要：

  The enzymatic resolutions of two racemic ethyl hydroxyalkane(P-phenyl)phosphinates were performed by both esterification and hydrolysis approaches. The first reaction was performed in anhydrous diisopropyl ether with triethylamine or pyridine as additives by using lipases from three different sources (Candida cylindracea, Aspergillus niger, and Mucor javanicus). The increase in enantioselectivity was observed when NEt3 was applied. The second reactionlipase-catalysed hydrolysis of ethyl butyryloxyalkane(P-phenyl)phosphinateswas carried out by Candida cylindracea lipase in diisopropyl ether saturated with water or in aqueous solutions containing MgCl2, LiCl, or Triton X-100. The usefulness of biphasic systems consisting of diisopropyl ether and water or aqueous solution of MgCl2, LiCl, or Triton X-100 also were tested. The use of biphasic system in the presence of Triton X-100 resulted in the higher conversion of the substrates.

  DOI：

  10.1080/10426500903365595

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
• Enzymatic Resolution of Ethyl α-Hydroxyphosphinates in a Modified Reaction Environment
  作者：Paulina Majewska、Barbara Lejczak、Paweł Kafarski

  DOI：10.1080/10426500903365595

  日期：2010.8.25

  The enzymatic resolutions of two racemic ethyl hydroxyalkane(P-phenyl)phosphinates were performed by both esterification and hydrolysis approaches. The first reaction was performed in anhydrous diisopropyl ether with triethylamine or pyridine as additives by using lipases from three different sources (Candida cylindracea, Aspergillus niger, and Mucor javanicus). The increase in enantioselectivity was observed when NEt3 was applied. The second reactionlipase-catalysed hydrolysis of ethyl butyryloxyalkane(P-phenyl)phosphinateswas carried out by Candida cylindracea lipase in diisopropyl ether saturated with water or in aqueous solutions containing MgCl2, LiCl, or Triton X-100. The usefulness of biphasic systems consisting of diisopropyl ether and water or aqueous solution of MgCl2, LiCl, or Triton X-100 also were tested. The use of biphasic system in the presence of Triton X-100 resulted in the higher conversion of the substrates.