diethyl (Z)-2-[(E)-1-(3-bromo-4-methoxyphenyl)prop-1-en-2-yl]but-2-enedioate | 1236067-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (Z)-2-[(E)-1-(3-bromo-4-methoxyphenyl)prop-1-en-2-yl]but-2-enedioate
• CAS: 1236067-06-3
• 化学式: C₁₈H₂₁BrO₅
• 分子量: 397.266
• InChiKey: UDQKFUPTLAFWDN-NTVQHCSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-vinylidenesuccinic acid diethyl ester 、 3-溴-4-甲氧基苯甲醛 在 三丁基膦 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以88%的产率得到diethyl (Z)-2-[(E)-1-(3-bromo-4-methoxyphenyl)prop-1-en-2-yl]but-2-enedioate
  参考文献：
  名称：

  Stereoselective Synthesis of 1,2,3,4-Tetrasubstituted Dienes from Allenoates and Aldehydes: An Observation of Phosphine-Induced Chemoselectivity

  摘要：

  Phosphine-mediated olefination between a-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo- and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.

  DOI：

  10.1021/ol101429z

文献信息

• Stereoselective Synthesis of 1,2,3,4-Tetrasubstituted Dienes from Allenoates and Aldehydes: An Observation of Phosphine-Induced Chemoselectivity
  作者：Silong Xu、Wen Zou、Guiping Wu、Haibin Song、Zhengjie He

  DOI：10.1021/ol101429z

  日期：2010.8.6

  Phosphine-mediated olefination between a-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo- and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.