(E)-1-(2-(3,4,5-trimethoxybenzylidene)cyclopropyl)-2-phenylethanone | 1195847-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-(2-(3,4,5-trimethoxybenzylidene)cyclopropyl)-2-phenylethanone
• CAS: 1195847-47-2
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: XLCKSJFDLMDLDK-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-(3,4,5-trimethoxybenzylidene)cyclopropyl)-2-phenylethanone 在 palladium diacetate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以88%的产率得到(3E,5E)-1-phenyl-6-(3,4,5-trimethoxyphenyl)hexa-3,5-dien-2-one
  参考文献：
  名称：

  Pd(0) or Pd(II)-catalyzed ring-opening reactions of benzylidene- and alkylidenecyclopropyl ketones and aldehydes

  摘要：

  Pd(0) catalyzed reactions of methylenecyclopropyl carbonyl compounds afforded a convenient method for the synthesis of conjugate (E,E)-1,3-diene derivatives 2 in good to excellent yields. Moreover, we also found that Pd(II)-catalyzed reactions of methylenecyclopropyl carbonyl compounds with water gave 1,5-diketones in good to high yields via a carbene-palladium intermediate. The plausible reaction mechanisms have also been provided on the basis of control and O-18-labeling experiments. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.044

文献信息

• Pd(0) or Pd(II)-catalyzed ring-opening reactions of benzylidene- and alkylidenecyclopropyl ketones and aldehydes
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1016/j.tet.2009.08.044

  日期：2009.10

  Pd(0) catalyzed reactions of methylenecyclopropyl carbonyl compounds afforded a convenient method for the synthesis of conjugate (E,E)-1,3-diene derivatives 2 in good to excellent yields. Moreover, we also found that Pd(II)-catalyzed reactions of methylenecyclopropyl carbonyl compounds with water gave 1,5-diketones in good to high yields via a carbene-palladium intermediate. The plausible reaction mechanisms have also been provided on the basis of control and O-18-labeling experiments. (c) 2009 Elsevier Ltd. All rights reserved.