(1α,2α,5α)-(-)-2-(2-propenyl)-4-oxo-3-azabicyclo[3.1.0]hexane-3-propanoic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1α,2α,5α)-(-)-2-(2-propenyl)-4-oxo-3-azabicyclo[3.1.0]hexane-3-propanoic acid methyl ester
• 英文别名: methyl 3-[(1S,4S,5R)-2-oxo-4-prop-2-enyl-3-azabicyclo[3.1.0]hexan-3-yl]propanoate
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: UMEJEEIPTPHPLL-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S,4S,5R)-3-[(1R)-2-hydroxy-1-phenylethyl]-4-prop-2-enyl-3-azabicyclo[3.1.0]hexan-2-one 在 potassium hydride 、 calcium 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 16.0h， 生成 (1α,2α,5α)-(-)-2-(2-propenyl)-4-oxo-3-azabicyclo[3.1.0]hexane-3-propanoic acid methyl ester
  参考文献：
  名称：

  An asymmetric synthesis of the key precursor to (−)-indolizomycin

  摘要：

  Using chiral bicyclic lactams, containing an alpha,beta-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00728-5

文献信息

• An asymmetric synthesis of the key precursor to (−)-indolizomycin
  作者：Michael D. Groaning、A.I. Meyers

  DOI：10.1016/s0040-4039(99)00728-5

  日期：1999.6

  Using chiral bicyclic lactams, containing an alpha,beta-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.