ethyl (E)-3-((1R,2R,3R)-2-benzoyl-3-phenylcyclopropyl)acrylate | 1027804-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (E)-3-((1R,2R,3R)-2-benzoyl-3-phenylcyclopropyl)acrylate
• 英文别名: ethyl (E)-3-[(1R,2R,3R)-2-benzoyl-3-phenylcyclopropyl]prop-2-enoate
• CAS: 1027804-31-4
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: UMBCBVXXVJYFLD-VSVQKKNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-benzoyl-3-phenyl-cyclopropanecarbaldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 生成 ethyl (Z)-3-((1R,2R,3R)-2-benzoyl-3-phenylcyclopropyl)acrylate 、 ethyl (E)-3-((1R,2R,3R)-2-benzoyl-3-phenylcyclopropyl)acrylate 、 ethyl (Z)-3-((1S,2S,3S)-2-benzoyl-3-phenylcyclopropyl)acrylate 、 ethyl (E)-3-((1S,2S,3S)-2-benzoyl-3-phenylcyclopropyl)acrylate
  参考文献：
  名称：

  Highly enantioselective tandem cyclopropanation/Wittig reaction of α,β-unsaturated aldehydes with arsonium ylides catalyzed by recyclable dendritic catalyst

  摘要：

  A novel tandem cyclopropanation/Wittig reaction of alpha,beta-unsaturated aldehydes with arsonium ylides using a chiral 2-trimethylsilanyloxy-methyl-pyrrolidine-based dendritic catalyst is described. Good yields (up to 86%), and high diastereoselectivities (up to dr = 99: 1) and enantioselectivities (up to 99% ee) were obtained under simple and mild reaction conditions. The catalyst can be recycled without any loss in activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.022

文献信息

• Highly enantioselective tandem cyclopropanation/Wittig reaction of α,β-unsaturated aldehydes with arsonium ylides catalyzed by recyclable dendritic catalyst
  作者：Yun-Hui Zhao、Chang-Wu Zheng、Gang Zhao、Wei-Guo Cao

  DOI：10.1016/j.tetasy.2008.02.022

  日期：2008.4

  A novel tandem cyclopropanation/Wittig reaction of alpha,beta-unsaturated aldehydes with arsonium ylides using a chiral 2-trimethylsilanyloxy-methyl-pyrrolidine-based dendritic catalyst is described. Good yields (up to 86%), and high diastereoselectivities (up to dr = 99: 1) and enantioselectivities (up to 99% ee) were obtained under simple and mild reaction conditions. The catalyst can be recycled without any loss in activity. (c) 2008 Elsevier Ltd. All rights reserved.