ethyl 2-ethynyl-2-hydroxy-1-(penta-3,4-dienyl)cyclohexanecarboxylate | 1037667-62-1

• 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: ethyl 2-ethynyl-2-hydroxy-1-(penta-3,4-dienyl)cyclohexanecarboxylate
• CAS: 1037667-62-1
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: IQTKLSUTOSYNOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  ethyl 2-ethynyl-2-hydroxy-1-(penta-3,4-dienyl)cyclohexanecarboxylate 、 一氧化碳 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 甲苯 为溶剂， 反应 3.17h， 以32%的产率得到ethyl 3,3a,4,5,5a,6,7,8,9,9a-decahydro-9a-hydroxy-3-methylene-2-oxo-2H-cyclopenta[a]naphthalene-5a-carboxylate
  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：

  2-oxo-1-(penta-3,4-dienyl)cyclohexanecarboxylic acid ethyl ester 、 乙炔基溴化镁 以 四氢呋喃 为溶剂， 反应 5.0h， 以89%的产率得到ethyl 2-ethynyl-2-hydroxy-1-(penta-3,4-dienyl)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