ethyl oct-1-en-3-yl allylphosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: ethyl oct-1-en-3-yl allylphosphonate
• 英文别名: 3-(Ethoxy-oxido-prop-2-enylphosphaniumyl)oxyoct-1-ene；3-(ethoxy-oxido-prop-2-enylphosphaniumyl)oxyoct-1-ene
• 化学式: C₁₃H₂₅O₃P
• 分子量: 260.313
• InChiKey: NDBVCJFRLOLRIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  41.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl oct-1-en-3-yl allylphosphonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 生成 diethyl (1Z,3E)-nona-1,3-dienylphosphonate
  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
• 作为产物：
  描述：

  1-辛烯-3-醇 、 2-propenyl-phosphonochloridic acid, ethyl ester 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到ethyl oct-1-en-3-yl allylphosphonate
  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.