(E)-3-((1R,2R,3R)-2-(4-bromobenzoyl)-3-phenylcyclopropyl)-1-(4-bromophenyl)prop-2-en-1-one | 1027804-22-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-3-((1R,2R,3R)-2-(4-bromobenzoyl)-3-phenylcyclopropyl)-1-(4-bromophenyl)prop-2-en-1-one
• 英文别名: (E)-3-[(1R,2R,3R)-2-(4-bromobenzoyl)-3-phenylcyclopropyl]-1-(4-bromophenyl)prop-2-en-1-one
• CAS: 1027804-22-3
• 化学式: C₂₅H₁₈Br₂O₂
• 分子量: 510.225
• InChiKey: YWECUFUNTZCMOW-LYHNGNHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-bromo-phenacyl)-triphenyl-arsonium; bromide 、 肉桂醛 在 L-prolinol-derived dendritic catalyst sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 3-(2-(4-bromobenzoyl)-3-phenylcyclopropyl)-1-(4-bromophenyl)prop-2-en-1-one 、 (E)-3-((1R,2R,3R)-2-(4-bromobenzoyl)-3-phenylcyclopropyl)-1-(4-bromophenyl)prop-2-en-1-one 、 (E)-3-((1S,2S,3S)-2-(4-bromobenzoyl)-3-phenylcyclopropyl)-1-(4-bromophenyl)prop-2-en-1-one
  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