[(R)-2-Benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-phenethyl-phosphinic acid | 439800-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: [(R)-2-Benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-phenethyl-phosphinic acid
• 英文别名: [(2R)-2-benzyl-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl]-(2-phenylethyl)phosphinic acid
• CAS: 439800-07-4
• 化学式: C₂₈H₃₀NO₅P
• 分子量: 491.524
• InChiKey: ZVRJCXKEKYGZBG-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(R)-2-Benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-phenethyl-phosphinic acid 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphinic acids with acrylate derivatives

  摘要：

  Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipepti-domimetics in excellent yields ( > 90%). Chiral induction of substituents at the alpha-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastercomeric and enantiorneric excesses (50-98%). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16-19 were also successfully separated by HPLC. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01388-2
• 作为产物：
  描述：

  苄基丙二酸 在 N-甲基吗啉 、 正丁基锂 、 二乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.0h， 生成 [(R)-2-Benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-phenethyl-phosphinic acid
  参考文献：
  名称：

  Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphinic acids with acrylate derivatives

  摘要：

  Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipepti-domimetics in excellent yields ( > 90%). Chiral induction of substituents at the alpha-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastercomeric and enantiorneric excesses (50-98%). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16-19 were also successfully separated by HPLC. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01388-2

文献信息

• Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphinic acids with acrylate derivatives
  作者：Xuewei Liu、X.Eric Hu、Xinrong Tian、Adam Mazur、Frank H Ebetino

  DOI：10.1016/s0022-328x(01)01388-2

  日期：2002.3

  Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipepti-domimetics in excellent yields ( > 90%). Chiral induction of substituents at the alpha-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastercomeric and enantiorneric excesses (50-98%). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16-19 were also successfully separated by HPLC. (C) 2002 Elsevier Science B.V. All rights reserved.