5-Oxo-2-pent-4-enyl-cyclopent-1-enecarboxylic acid cyclohexyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-Oxo-2-pent-4-enyl-cyclopent-1-enecarboxylic acid cyclohexyl ester
• 英文别名: Cyclohexyl 5-oxo-2-pent-4-enylcyclopentene-1-carboxylate
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: MEDHQYIERBLHFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-乙氧基-1-三甲硅氧基环丙烷 、 Oct-7-en-2-ynoic acid cyclohexyl ester 在 copper(I) bromide dimethylsulfide complex zinc(II) chloride 作用下， 生成 5-Oxo-2-pent-4-enyl-cyclopent-1-enecarboxylic acid cyclohexyl 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.