(1Z,3E)-4-phenylbuta-1,3-dienylphosphonic acid monoethyl ester | 1449782-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1Z,3E)-4-phenylbuta-1,3-dienylphosphonic acid monoethyl ester
• 英文别名: ethoxy-[(1Z,3E)-4-phenylbuta-1,3-dienyl]phosphinic acid
• CAS: 1449782-62-0
• 化学式: C₁₂H₁₅O₃P
• 分子量: 238.223
• InChiKey: XBPMDHLCWIVKFM-QZTBCQRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯基-2-丙烯-1-醇 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 17.0h， 生成 (1Z,3E)-4-phenylbuta-1,3-dienylphosphonic acid monoethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Dienyl Phosphonates via Extended Tethered Ring-Closing Metathesis

  摘要：

  Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring-opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1Z,3E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the diastereoselectivity of the sequence.

  DOI：

  10.1021/ol4020078

文献信息

• Stereoselective Synthesis of Dienyl Phosphonates via Extended Tethered Ring-Closing Metathesis
  作者：Bernd Schmidt、Oliver Kunz

  DOI：10.1021/ol4020078

  日期：2013.9.6

  Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring-opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1Z,3E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the diastereoselectivity of the sequence.