diethyl (1Z,3E)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)buta-1,3-dienylphosphonate | 1449782-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (1Z,3E)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)buta-1,3-dienylphosphonate
• 英文别名: (4S)-4-[(1E,3Z)-4-[diethoxy(oxido)phosphaniumyl]buta-1,3-dienyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 1449782-75-5
• 化学式: C₁₃H₂₃O₅P
• 分子量: 290.296
• InChiKey: HGPKQTSXCLVWQY-SJPFIRGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol 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 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 2.0h， 生成 diethyl (1Z,3E)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)buta-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

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.