ethyl 1-(cyclohex-1-enylethynyl)-2-oxocyclopentanecarboxylate | 121721-19-5

• 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: ethyl 1-(cyclohex-1-enylethynyl)-2-oxocyclopentanecarboxylate
• 英文别名: 1-(cyclohex-1-enylethynyl)-2-oxo-cyclopentanecar boxylic acid ethyl ester；Ethyl 1-[2-(cyclohexen-1-yl)ethynyl]-2-oxocyclopentane-1-carboxylate
• CAS: 121721-19-5
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: UQFUBTIHTKFOJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  ethyl 1-(cyclohex-1-enylethynyl)-2-oxocyclopentanecarboxylate 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以83%的产率得到2-Cyclohex-1-enylvinylidene-hexanedioic acid 1-ethyl ester
  参考文献：
  名称：

  Facile generation method for conjugated allenyl esters based on retro-Dieckmann-type ring-opening reactions

  摘要：

  alpha-Alkynyl-alpha-ethoxycarbonyl cyclopentanones 1a-c and cyclohexanones 2a-c were readily synthesized by the reaction of ethyl 2-oxocyclopentanonecarboxylate 6 and ethyl 2-oxocyclohexanonecarboxylate 7 with alkynyllead triacetates 5a-c obtained from lithium acetylides 4a-c and lead tetraacetate. Treatment of 1a-c and 2a-c with 1 N KOH in THF or with n-Bu4N+OEt+ in EtOH and THF gave the corresponding conjugated allenyl esters 8a-c, 9a-c, 10a-c, and 11a-c in good to excellent yields, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.138
• 作为产物：
  描述：

  1-乙炔基环己烷 、 2-氧代环戊羧酸乙酯 在 lead(IV) acetate 、 正丁基锂 、 三甲基氯化锡 作用下， 生成 ethyl 1-(cyclohex-1-enylethynyl)-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Moloney, Mark G.; Pinhey, John T.; Roche, Eric G., Journal of the Chemical Society. Perkin transactions I, 1989, p. 333 - 341

  摘要：

  DOI：

文献信息

• Moloney, Mark G.; Pinhey, John T.; Roche, Eric G., Journal of the Chemical Society. Perkin transactions I, 1989, p. 333 - 341
  作者：Moloney, Mark G.、Pinhey, John T.、Roche, Eric G.

  DOI：——

  日期：——
• MOLONEY, MARK G.;PINHEY, JOHN T.;ROCHE, ERIC G., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 333-341
  作者：MOLONEY, MARK G.、PINHEY, JOHN T.、ROCHE, ERIC G.

  DOI：——

  日期：——
• Facile generation method for conjugated allenyl esters based on retro-Dieckmann-type ring-opening reactions
  作者：Shigeki Sano、Hisashi Shimizu、Yoshimitsu Nagao

  DOI：10.1016/j.tetlet.2005.02.138

  日期：2005.4

  alpha-Alkynyl-alpha-ethoxycarbonyl cyclopentanones 1a-c and cyclohexanones 2a-c were readily synthesized by the reaction of ethyl 2-oxocyclopentanonecarboxylate 6 and ethyl 2-oxocyclohexanonecarboxylate 7 with alkynyllead triacetates 5a-c obtained from lithium acetylides 4a-c and lead tetraacetate. Treatment of 1a-c and 2a-c with 1 N KOH in THF or with n-Bu4N+OEt+ in EtOH and THF gave the corresponding conjugated allenyl esters 8a-c, 9a-c, 10a-c, and 11a-c in good to excellent yields, respectively. (c) 2005 Elsevier Ltd. All rights reserved.