7-Chloro-4-ethyl-hept-2-ynoic acid tert-butyl ester | 151860-36-5

• 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: 7-Chloro-4-ethyl-hept-2-ynoic acid tert-butyl ester
• 英文别名: Tert-butyl 7-chloro-4-ethylhept-2-ynoate
• CAS: 151860-36-5
• 化学式: C₁₃H₂₁ClO₂
• 分子量: 244.762
• InChiKey: FDDMFIFYVANTPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  7-Chloro-4-ethyl-hept-2-ynoic acid tert-butyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 丙酮 、 苯 为溶剂， 反应 20.5h， 生成 [2-Ethyl-cyclopent-(Z)-ylidene]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Metal-halogen exchange-initiated intramolecular conjugate addition reactions of conjugated acetylenic esters

  摘要：

  The lithium-iodine exchange-initiated intramolecular conjugate addition reactions of some model gamma-iodo-alpha,beta-acetylenic esters have been examined. Product mixtures arising from proton abstraction reactions were observed in reactions leading to 5-membered ring formation. More efficient cyclizations resulted when reactions were conducted in the presence of trimethylsilyl chloride to trap intermediate allenolate ions. Allenolate ion trapping by an internal electrophilic center in 26 resulted in the highly efficient formation of bicyclic ester 27.

  DOI：

  10.1021/jo00076a053
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1,1-dibromo-6-chloro-3-ethyl-1-hexene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到7-Chloro-4-ethyl-hept-2-ynoic acid tert-butyl ester
  参考文献：
  名称：

  Metal-halogen exchange-initiated intramolecular conjugate addition reactions of conjugated acetylenic esters

  摘要：

  The lithium-iodine exchange-initiated intramolecular conjugate addition reactions of some model gamma-iodo-alpha,beta-acetylenic esters have been examined. Product mixtures arising from proton abstraction reactions were observed in reactions leading to 5-membered ring formation. More efficient cyclizations resulted when reactions were conducted in the presence of trimethylsilyl chloride to trap intermediate allenolate ions. Allenolate ion trapping by an internal electrophilic center in 26 resulted in the highly efficient formation of bicyclic ester 27.

  DOI：

  10.1021/jo00076a053