2-oxo-1-(penta-3,4-dienyl)cyclohexanecarboxylic acid ethyl ester

• 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-oxo-1-(penta-3,4-dienyl)cyclohexanecarboxylic acid ethyl ester
• 英文别名: ethyl 2-oxo-1-(penta-3,4-dienyl)cyclohexanecarboxylate
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: BUVHESYGYPNCSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-1-(penta-3,4-dienyl)cyclohexanecarboxylic acid ethyl ester 、 1-丙炔溴化镁 以 四氢呋喃 为溶剂， 反应 4.0h， 以97%的产率得到ethyl 2-hydroxy-1-(penta-3,4-dienyl)-2-(prop-1-ynyl)cyclohexanecarboxylate
  参考文献：
  名称：

  A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction

  摘要：

  Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.

  DOI：

  10.1021/jo8007258
• 作为产物：
  描述：

  5-碘-戊-1,2-二烯 、 2-环己酮甲酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以60%的产率得到2-oxo-1-(penta-3,4-dienyl)cyclohexanecarboxylic acid ethyl ester
  参考文献：
  名称：

  A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction

  摘要：

  Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.

  DOI：

  10.1021/jo8007258

文献信息

• Ketyl−Allene Cyclizations Promoted by Samarium(II) Iodide
  作者：Gary A. Molander、Elizabeth Pollina Cormier

  DOI：10.1021/jo047887s

  日期：2005.4.1

  Samarium(II) iodide has proven to be an effective reagent for intramolecular reductive coupling reactions. Previous investigations of intramolecular ketyl−olefin coupling reactions provided carbocycles in excellent yield and good diastereoselectivity. This method has been extended to ketyl cyclizations with allenes. Substrates leading to both carbocycles and heterocycles in a selective manner are explored

  碘化已被证明是分子内还原偶联反应的有效试剂。分子内酮基-烯烃偶联反应的先前研究提供了具有优异收率和良好非对映选择性的碳环。该方法已扩展到用烯丙基环进行酮基环化反应。探索了以选择性方式导致碳环和杂环的底物。
• A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction
  作者：Kay M. Brummond、Daitao Chen、Matthew M. Davis

  DOI：10.1021/jo8007258

  日期：2008.7.1

  Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.