(3R,5aS,6aR,6bS)-3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-one | 241466-62-6

• 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: (3R,5aS,6aR,6bS)-3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-one
• 英文别名: (1S,2R,4S,7R)-7-phenyl-9-oxa-6-azatricyclo[4.3.0.02,4]nonan-5-one
• CAS: 241466-62-6
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: HIBRYNKZJGWSTF-NOHGZBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,5aS,6aR,6bS)-3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-one 在 四氯化钛 、 potassium hydride 、 calcium 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 为溶剂， 反应 21.0h， 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
• 作为产物：
  描述：

  (3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮 在 苯甲砜 、 potassium hydride 作用下， 以 甲苯 为溶剂， 生成 (3R,5aS,6aR,6bS)-3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-one
  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

• Diastereospecific Intramolecular Cyclopropanation of Enantiopure 8-Bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-ones
  作者：María L. Orea、Dino Gnecco、Anna Vargas、David M. Aparicio、Joel L. Terán、Jorge R. Juárez

  DOI：10.3987/com-17-13834

  日期：——

  stereospecificity of the reaction with respect to the double bond geometry and its compatibility with a wide range of functional groups. The chemoselectivity of the reaction toward some olefins is excellent and very few side reactions are observed with functionalized substrates.2,3 Many of these reactions proceed in a cheletropic manner and several methods exist for converting alkenes to cyclopropane rings

  (3R,8R,8aS)-8-bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-one 1 和 (3R,8S,8aS)-8-bromo-3-phenylhexahydrooxazolo[描述了 3,2-a]pyridin-5-one 2 以高产率生成相应的对映纯 3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-ones 3 和 4 . 手性环丙烷的合成仍然是一个相当大的挑战，特别是由于环丙烷环经常存在于各种天然产物和生物活性化合物中。有机化学家一直对环丙烷亚基着迷，它已经并将继续在有机化学中发挥重要作用。其应变结构、有趣的键合特性和作为内部机械探针的价值引起了物理有机界的关注。1 Simmons-Smith 环丙烷化反应是有机化学家将烯烃转化为环丙烷的最广泛使用的反应之一。这种流