diethyl (1S,2S)-1,2-dihydroxy-2-(4-chlorophenyl)ethylphosphonate

• 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: diethyl (1S,2S)-1,2-dihydroxy-2-(4-chlorophenyl)ethylphosphonate
• 英文别名: diethyl (1S,2S)-dihydroxy-2-(p-chlorophenyl)ethanephosphonate；(1S,2S)-1-(4-chlorophenyl)-2-diethoxyphosphorylethane-1,2-diol
• 化学式: C₁₂H₁₈ClO₅P
• 分子量: 308.699
• InChiKey: IQZJIJBMIHGELO-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 在 potassium osmate(VI) AD-mix-α 、 正丁基锂 、 甲基磺酰胺 作用下， 以 正己烷 、 水 、 叔丁醇 为溶剂， 反应 55.2h， 生成 diethyl (1S,2S)-1,2-dihydroxy-2-(4-chlorophenyl)ethylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6

文献信息

• Quinine as chiral discriminator for determination of enantiomeric excess of diethyl 1,2-dihydroxyalkanephosphonates
  作者：Alina Maly、Barbara Lejczak、Pawel Kafarski

  DOI：10.1016/s0957-4166(03)00177-0

  日期：2003.4

  2-dihydroxyethanephosphonates obtained either by chemical or biocatalytic synthesis. Sharpless asymmetric dihydroxylation of diethyl trans-vinylphosphonates enabled differentiation of threo and erythro isomers of 1,2-dihydroxyphosphonates, and provided standards for the determination of the absolute configuration of each of enantiomeric pair of threo isomers.

  奎宁用作31 P NMR变换试剂，用于测定通过化学或生物催化合成获得的对映体过量的1,2-二羟基乙烷膦酸二乙酯。二乙基反式乙烯基膦酸酯的不尖锐的不对称二羟基化使得能够区分1,2-二羟基膦酸酯的苏式和赤型异构体，并为确定每个对映体对苏式异构体的绝对构型提供了标准。
• Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents
  作者：Tsutomu Yokomatsu、Takehiro Yamagishi、Kenji Suemune、Yoshinori Yoshida、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(97)10341-6

  日期：1998.1

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.