2-benzoyl-3-phenylcyclopropanecarbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyl-3-phenylcyclopropanecarbaldehyde
• 英文别名: 2-benzoyl-3-phenylcyclopropane-1-carbaldehyde
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: JAWHAAIAYFZUPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-phenylcyclopropanecarbaldehyde 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 [(1R,2S,3R)-2-benzoyl-3-phenylcyclopropyl]methanol 、
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives

  摘要：

  N-Heterocyclic carbene catalyzed ring expansion of readily accessible 2-acyl-l-formylcyclopropanes was developed. With 5 mol % of triazoliurn salt 5 and 30 mol % of DBU, ring expansion of various 2-acyl-l-formylcyclopropanes led to 3,4-dihydro-alpha-pyrones in good to excellent yields.

  DOI：

  10.1021/ol9002898
• 作为产物：
  描述：

  反式肉桂醛 、 (benzoylmethylene)dimethylsulfurane 在 (-)-5-[(S)-indoline-2-yl]tetrazole 作用下， 以 氯仿 为溶剂， 生成 2-benzoyl-3-phenyl-cyclopropanecarbaldehyde 、 2-benzoyl-3-phenylcyclopropanecarbaldehyde
  参考文献：
  名称：

  Tetrazolic Acid Functionalized Dihydroindol:  Rational Design of a Highly Selective Cyclopropanation Organocatalyst

  摘要：

  Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of alpha,beta-unsaturated aldehydes with sulfur ylides. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized product in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted alpha,beta-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.

  DOI：

  10.1021/jo070519e

文献信息

• Organocatalytic asymmetric cyclopropanation of α,β-unsaturated aldehydes with arsonium ylides
  作者：Yun-Hui Zhao、Gang Zhao、Wei-Guo Cao

  DOI：10.1016/j.tetasy.2007.10.007

  日期：2007.10

  A novel organocatalytic asymmetric cyclopropanation of alpha,beta-unsaturated aldehydes with arsonium ylides using diphenylprolinol silylether as a catalyst is described. A variety of chiral cyclopropyl aldehydes are obtained in moderate to good yields with up to 99:1 dr (diastereomeric ratio) and 99% ee under simple and mild reaction conditions. (c) 2007 Elsevier Ltd. All rights reserved.