ethyl butyryloxy(phenyl)methane(P-phenyl)phosphinate | 866612-47-7

• 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 butyryloxy(phenyl)methane(P-phenyl)phosphinate
• 英文别名: ethyl 1-butyryloxy-1-phenylmethane(P-phenyl)phosphinate；[Ethoxy(phenyl)phosphoryl](phenyl)methyl butanoate；[[ethoxy(phenyl)phosphoryl]-phenylmethyl] butanoate
• CAS: 866612-47-7
• 化学式: C₁₉H₂₃O₄P
• 分子量: 346.363
• InChiKey: UTMIEVSZSOVTTB-UHFFFAOYSA-N

物化性质

• 沸点：
  452.9±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl butyryloxy(phenyl)methane(P-phenyl)phosphinate 在 Porcine Pancreas Lipase dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 水 作用下， 以 正己烷 、 异丙醚 为溶剂， 反应 1.0h， 生成 ((R)-Hydroxy-phenyl-methyl)-phenyl-phosphinic acid ethyl ester 、 Butyric acid (S)-(ethoxy-phenyl-phosphinoyl)-phenyl-methyl ester
  参考文献：
  名称：

  Majewska; Kafarski; Lejczak, Polish Journal of Chemistry, 2005, vol. 79, # 3, p. 561 - 566

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl Phenylphosphinate 在 aluminum oxide 、 potassium fluoride 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 ethyl butyryloxy(phenyl)methane(P-phenyl)phosphinate
  参考文献：
  名称：

  Majewska; Kafarski; Lejczak, Polish Journal of Chemistry, 2005, vol. 79, # 3, p. 561 - 566

  摘要：

  DOI：

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.