4-Acetoxy-5-methyl-hex-2-ynoic acid ethyl ester | 128114-06-7

• 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-Acetoxy-5-methyl-hex-2-ynoic acid ethyl ester
• 英文别名: Ethyl 4-acetyloxy-5-methylhex-2-ynoate
• CAS: 128114-06-7
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: WITYHXUMEAWYHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(2-carboethoxyethyl)zinc 、 4-Acetoxy-5-methyl-hex-2-ynoic acid ethyl ester 在 六甲基磷酰三胺 、 三甲基氯硅烷 作用下， 以 乙醚 为溶剂， 以49%的产率得到2-(1-Acetoxy-2-methyl-propyl)-5-oxo-cyclopent-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

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

  摘要：

  DOI：

  10.1021/jo00301a003
• 作为产物：
  描述：

  ethyl 4-hydroxy-5-methyl-2-hexynoate 、 乙酰氯 在 4-二甲氨基吡啶 、 2-丙炔-1-醇 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-Acetoxy-5-methyl-hex-2-ynoic acid ethyl ester
  参考文献：
  名称：

  Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes

  摘要：

  In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.

  DOI：

  10.1021/jo900102w

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.
• CRIMMINS, MICHAEL T.;NANTERMET, PHILIPPE G., J. ORG. CHEM., 55,(1990) N4, C. 4235-4237
  作者：CRIMMINS, MICHAEL T.、NANTERMET, PHILIPPE G.

  DOI：——

  日期：——
• Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes
  作者：C. Wade Downey、Brian D. Mahoney、Vincent R. Lipari

  DOI：10.1021/jo900102w

  日期：2009.4.3

  In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.
• Addition of zinc homoenolates to acetylenic esters: a formal [3+2] cycloaddition
  作者：Michael T. Crimmins、Philippe G. Nantermet

  DOI：10.1021/jo00301a003

  日期：1990.7