[(4S)-4-benzyl-2-oxo-5,5-diphenyl-oxazolidin-3-yl]-phosphonic acid diethyl ester

• 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: [(4S)-4-benzyl-2-oxo-5,5-diphenyl-oxazolidin-3-yl]-phosphonic acid diethyl ester
• 英文别名: (4S)-4-benzyl-3-[diethoxy(oxido)phosphaniumyl]-5,5-diphenyl-1,3-oxazolidin-2-one
• 化学式: C₂₆H₂₈NO₅P
• 分子量: 465.486
• InChiKey: HFOXBTVFSISCMV-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(4S)-4-benzyl-2-oxo-5,5-diphenyl-oxazolidin-3-yl]-phosphonic acid diethyl ester 、 苏合香醇 在 甲基氯化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 以14%的产率得到
  参考文献：
  名称：

  Examining the origin of selectivity in the reaction of racemic alcohols with chiral N-phosphoryl oxazolidinones

  摘要：

  A range of known and novel N-phosphoryl oxazolidinones and imidazolidinones were prepared and screened in the kinetic resolution of a range of racemic magnesium chloroalkoxides. Models are proposed to account for the enantioselectivity achieved based on a combination of chiral relay effects, generation of transient stereochemistry and the structure of the intermediate magnesium alkoxide. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/3.0/).

  DOI：

  10.1016/j.tetasy.2014.08.003
• 作为产物：
  描述：

  氯磷酸二乙酯 、 (4S)-4-苄基-5,5-二苯基-2-恶唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到[(4S)-4-benzyl-2-oxo-5,5-diphenyl-oxazolidin-3-yl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Stereochemical consequences of the use of chiral N-phosphoryl oxazolidinones in the attempted kinetic resolution of bromomagnesium alkoxides

  摘要：

  A number of chiral N-phosphoryl oxazolidinones have been prepared and evaluated as asymmetric phosphoryl transfer agents with the magnesium alkoxide of 1-phenyl ethanol. The reaction proceeded with little stereo selection, which was shown to be a consequence of the reaction mechanism that occurs with inversion of configuration at phosphorus consistent with in-line attack opposite the leaving group. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.025

文献信息

• Examining the origin of selectivity in the reaction of racemic alcohols with chiral N-phosphoryl oxazolidinones
  作者：Samuel Crook、Nigel J. Parr、Jonathan Simmons、Simon Jones

  DOI：10.1016/j.tetasy.2014.08.003

  日期：2014.10

  A range of known and novel N-phosphoryl oxazolidinones and imidazolidinones were prepared and screened in the kinetic resolution of a range of racemic magnesium chloroalkoxides. Models are proposed to account for the enantioselectivity achieved based on a combination of chiral relay effects, generation of transient stereochemistry and the structure of the intermediate magnesium alkoxide. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/3.0/).
• Stereochemical consequences of the use of chiral N-phosphoryl oxazolidinones in the attempted kinetic resolution of bromomagnesium alkoxides
  作者：Simon Jones、Dimitrios Selitsianos

  DOI：10.1016/j.tetasy.2005.08.025

  日期：2005.9

  A number of chiral N-phosphoryl oxazolidinones have been prepared and evaluated as asymmetric phosphoryl transfer agents with the magnesium alkoxide of 1-phenyl ethanol. The reaction proceeded with little stereo selection, which was shown to be a consequence of the reaction mechanism that occurs with inversion of configuration at phosphorus consistent with in-line attack opposite the leaving group. (C) 2005 Elsevier Ltd. All rights reserved.