2-methyl-4-penten-2-yl 3-butenoate | 1092695-27-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-methyl-4-penten-2-yl 3-butenoate
• 英文别名: 2-Methylpent-4-en-2-yl but-3-enoate
• CAS: 1092695-27-6
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: HGOHNVWVIMGDGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-4-penten-2-yl 3-butenoate 在 aluminum tris(2,6-diphenylphenoxide) 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 以76%的产率得到6,6-dimethyl-3,4-dehydro ε-lactone
  参考文献：
  名称：

  Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones

  摘要：

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

  DOI：

  10.1021/ol8022227
• 作为产物：
  描述：

  2-甲-4-戊烯-2-醇 、 丁-3-烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-4-penten-2-yl 3-butenoate
  参考文献：
  名称：

  Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones

  摘要：

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

  DOI：

  10.1021/ol8022227