(S)-3-[(E)-3-(2,6-difluorophenyl)prop-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one | 511268-07-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S)-3-[(E)-3-(2,6-difluorophenyl)prop-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one
• 英文别名: (4S)-3-[(E)-3-(2,6-difluorophenyl)prop-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 511268-07-8
• 化学式: C₁₈H₁₃F₂NO₃
• 分子量: 329.303
• InChiKey: LLORLFLKULIQHO-ZNFPLGDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚甘氨酸 、 (S)-3-[(E)-3-(2,6-difluorophenyl)prop-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one 、 N-(2-benzoylphenyl)-2-(piperidin-1-yl)acetamide 在 氢氧化钾 、 nickel(II) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 生成 (2S,3R)-3-(2,6-difluorophenyl)-5-oxopyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids

  摘要：

  A new series of achiral glycine equivalents have been evaluated with respect to their synthetic utility for the production of beta-substituted pyroglutamic acid derivatives. Among them, the piperidine-de rived complex was found to be a superior glycine derivative for the Michael additions with various (R)-N-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones representing a general and practical synthesis of sterically constrained beta-substituted pyroglutamic acids. In particular, application of complex allowed for the first time preparation of the corresponding isopropyl derivatives thus increasing the synthetic efficiency and expanding generality these Michael addition reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.093
• 作为产物：
  描述：

  反-2,6-二氟苯乙烯甲酸 在 氯化亚砜 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-3-[(E)-3-(2,6-difluorophenyl)prop-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A Convenient, Room-Temperature–Organic Base Protocol for Preparing Chiral 3-(Enoyl)-1,3-oxazolidin-2-ones

  摘要：

  In this study, we developed a new protocol for the preparation of the chiral 3-[(E)-enoyl]-1,3-oxazolidin-2-ones under the ultimately simple reaction conditions starting with the corresponding enoyl chlorides and 1,3-oxazolidin-2-ones with Et3N/LiCl at room temperature. The method generally allows efficient preparation of various derivatives regardless of the steric and electronic nature of the substituents on both the enoyl or the oxazolidinone sites. Excellent yields, combined with the simplicity of the experimental procedures, render the present method immediately useful for preparing the target compounds.

  DOI：

  10.1002/1522-2675(200211)85:11<3616::aid-hlca3616>3.0.co;2-o

文献信息

• A Convenient, Room-Temperature–Organic Base Protocol for Preparing Chiral 3-(Enoyl)-1,3-oxazolidin-2-ones
  作者：Vadim A. Soloshonok、Hisanori Ueki、Changchun Jiang、Chaozhong Cai、Victor J. Hruby

  DOI：10.1002/1522-2675(200211)85:11<3616::aid-hlca3616>3.0.co;2-o

  日期：2002.11

  In this study, we developed a new protocol for the preparation of the chiral 3-[(E)-enoyl]-1,3-oxazolidin-2-ones under the ultimately simple reaction conditions starting with the corresponding enoyl chlorides and 1,3-oxazolidin-2-ones with Et3N/LiCl at room temperature. The method generally allows efficient preparation of various derivatives regardless of the steric and electronic nature of the substituents on both the enoyl or the oxazolidinone sites. Excellent yields, combined with the simplicity of the experimental procedures, render the present method immediately useful for preparing the target compounds.
• Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids
  作者：Vadim A. Soloshonok、Hisanori Ueki、Trevor K. Ellis、Takeshi Yamada、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2004.12.093

  日期：2005.2

  A new series of achiral glycine equivalents have been evaluated with respect to their synthetic utility for the production of beta-substituted pyroglutamic acid derivatives. Among them, the piperidine-de rived complex was found to be a superior glycine derivative for the Michael additions with various (R)-N-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones representing a general and practical synthesis of sterically constrained beta-substituted pyroglutamic acids. In particular, application of complex allowed for the first time preparation of the corresponding isopropyl derivatives thus increasing the synthetic efficiency and expanding generality these Michael addition reactions. (C) 2004 Elsevier Ltd. All rights reserved.