[L-(cis)]-N-(t-butoxycarbonyl)-2-[1'-ethenyl-2'-fluoro-2'-ethoxycarbonyl]pyrrolidine | 356788-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: [L-(cis)]-N-(t-butoxycarbonyl)-2-[1'-ethenyl-2'-fluoro-2'-ethoxycarbonyl]pyrrolidine
• 英文别名: tert-butyl (2S)-2-[(E)-3-ethoxy-2-fluoro-3-oxoprop-1-enyl]pyrrolidine-1-carboxylate
• CAS: 356788-88-0
• 化学式: C₁₄H₂₂FNO₄
• 分子量: 287.331
• InChiKey: QBUNZCYJXUNMJO-SPQRFVMMSA-N

物化性质

• 沸点：
  353.8±37.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [L-(cis)]-N-(t-butoxycarbonyl)-2-[1'-ethenyl-2'-fluoro-2'-ethoxycarbonyl]pyrrolidine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以92%的产率得到ethyl (E)-2-fluoro-3-[(2S)-pyrrolidin-1-ium-2-yl]prop-2-enoate;chloride
  参考文献：
  名称：

  Enantioselective synthesis of α,β-unsaturated γ- and δ-lactams

  摘要：

  An enantioselective synthesis of alpha,beta -unsaturated gamma- and delta -lactams was proposed based on a simple strategy using the initial preparation of c is vinylogous aminoesters by the Horner reaction followed by a mild intramolecular cyclisation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00561-5
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 、 ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate lithium salt 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到[L-(cis)]-N-(t-butoxycarbonyl)-2-[1'-ethenyl-2'-fluoro-2'-ethoxycarbonyl]pyrrolidine
  参考文献：
  名称：

  Enantioselective synthesis of α,β-unsaturated γ- and δ-lactams

  摘要：

  An enantioselective synthesis of alpha,beta -unsaturated gamma- and delta -lactams was proposed based on a simple strategy using the initial preparation of c is vinylogous aminoesters by the Horner reaction followed by a mild intramolecular cyclisation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00561-5

文献信息

• Stereoselective synthesis of vinylogous peptides
  作者：Claude Grison、Stéphane Genève、Etienne Halbin、Philippe Coutrot

  DOI：10.1016/s0040-4020(01)00433-1

  日期：2001.6

  A trans or cis ethenyl group has been inserted between the α-carbon and the carboxyl group of α-aminoacids by Horner stereoselective olefination of α-aminoaldehydes. Numerous pure cis and trans vinylogous α-aminoacids have been obtained thus and coupled with aminopartners by classical methods. The versatility of the method was illustrated by the preparation of a [trans vinylogous-Gly3]Leu-enkephalin

  通过α-氨基醛的霍纳立体选择性烯化，将反式或顺式乙烯基插入α-氨基酸的α-碳和羧基之间。因此已经获得了许多纯的顺式和反式乙烯基α-氨基酸，并通过经典方法与氨基配偶体偶联。该方法的多功能性通过制备[反式乙烯基-Gly 3 ]亮脑啡肽来说明。
• Enantioselective synthesis of α,β-unsaturated γ- and δ-lactams
  作者：Claude Grison、Stéphane Genève、Philippe Coutrot

  DOI：10.1016/s0040-4039(01)00561-5

  日期：2001.6

  An enantioselective synthesis of alpha,beta -unsaturated gamma- and delta -lactams was proposed based on a simple strategy using the initial preparation of c is vinylogous aminoesters by the Horner reaction followed by a mild intramolecular cyclisation. (C) 2001 Elsevier Science Ltd. All rights reserved.