4-Hydroxy-7-methyl-oct-7-en-2-ynoic acid ethyl ester | 147165-29-5

• 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: 4-Hydroxy-7-methyl-oct-7-en-2-ynoic acid ethyl ester
• 英文别名: Ethyl 4-hydroxy-7-methyloct-7-en-2-ynoate
• CAS: 147165-29-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: HWULVJLQLPIUFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-7-methyl-oct-7-en-2-ynoic acid ethyl ester 在 三甲基氯硅烷 、 N,N-二异丙基乙胺 、 lithium chloride 、 zinc(II) chloride 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (3aS,4aR,7S,7aR)-7-Methoxymethoxy-4a-methyl-3-oxo-hexahydro-cyclobuta[1,2:1,4]dicyclopentene-3a-carboxylic acid ethyl ester
  参考文献：
  名称：

  环丁烷的自由基裂解：中环稠合碳环的一种制备方法

  摘要：

  锌-铜介导的共轭加成环化，分子内[2 + 2]光环加成和自由基断裂反应的结合提供了以良好的总收率使用各种中环稠合碳环系统的途径。

  DOI：

  10.1016/0040-4039(96)01433-5
• 作为产物：
  描述：

  4-甲基-4-戊烯醛 、 丙炔酸乙酯 在 lithium diisopropyl amide 作用下， 生成 4-Hydroxy-7-methyl-oct-7-en-2-ynoic acid ethyl ester
  参考文献：
  名称：

  Addition of zinc homoenolates to acetylenic esters and amides: a formal [3 + 2] cycloaddition

  摘要：

  The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described. The zinc homoenolate is prepared from [(ethoxycyclopropyl)oxy]trimethylsilane and zinc chloride in ether. Addition of an acetylenic amide or ester provides 2-carboxamido-or 2-carboalkoxy-3-alkylcyclopent-2-en-1-ones in good to excellent yields. The reaction can be carried out in the presence of a variety of sensitive functional groups including epoxides, alpha,beta-unsaturated esters, acetals, silyl ethers, and furans.

  DOI：

  10.1021/jo00057a013

文献信息

• Addition of zinc homoenolates to acetylenic esters and amides: a formal [3 + 2] cycloaddition
  作者：Michael T. Crimmins、Philippe G. Nantermet、B. Wesley Trotter、Isabelle M. Vallin、Paul S. Watson、Lynne A. McKerlie、Tracy L. Reinhold、Adrian Wai Hing Cheung、Katherine A. Stetson

  DOI：10.1021/jo00057a013

  日期：1993.2

  The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described. The zinc homoenolate is prepared from [(ethoxycyclopropyl)oxy]trimethylsilane and zinc chloride in ether. Addition of an acetylenic amide or ester provides 2-carboxamido-or 2-carboalkoxy-3-alkylcyclopent-2-en-1-ones in good to excellent yields. The reaction can be carried out in the presence of a variety of sensitive functional groups including epoxides, alpha,beta-unsaturated esters, acetals, silyl ethers, and furans.
• Radical fragmentation of cyclobutanes: An approach to medium ring fused carbocycles
  作者：Michael T. Crimmins、Sujuan Huang、Lisa E. Guise-Zawacki

  DOI：10.1016/0040-4039(96)01433-5

  日期：1996.9

  The combination of a zinc-copper mediated conjugate addition-cyclization, an intramolecular [2+2] photocycloaddition, and a radical fragmentation reaction provides access to a variety of medium ring fused carbocyclic systems in good overall yields.

  锌-铜介导的共轭加成环化，分子内[2 + 2]光环加成和自由基断裂反应的结合提供了以良好的总收率使用各种中环稠合碳环系统的途径。