2-(2-Cyclohexylidene-ethyl)-4,4,4-trifluoro-2-methyl-3-oxo-butyric acid ethyl ester | 136425-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-(2-Cyclohexylidene-ethyl)-4,4,4-trifluoro-2-methyl-3-oxo-butyric acid ethyl ester
• 英文别名: ethyl 2-(2-cyclohexylideneethyl)-4,4,4-trifluoro-2-methyl-3-oxobutanoate
• CAS: 136425-04-2
• 化学式: C₁₅H₂₁F₃O₃
• 分子量: 306.325
• InChiKey: SRQHSYOGUTURLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-Cyclohexylidene-ethyl)-4,4,4-trifluoro-2-methyl-3-oxo-butyric acid ethyl ester 在 sodium ethanolate 、 二氯乙基铝 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 101.0h， 生成 Ethyl 1-hydroxy-1-(trifluoromethyl)-2-methyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Lewis acid induced ene cyclization of .omega.-olefinic trifluoromethyl ketones: access to bicyclic compounds bearing a trifluoromethyl group

  摘要：

  Lewis acid induced ene cyclization of omega-olefinic trifluoromethyl ketones provides (trifluoromethyl)decalins and (trifluoromethyl)hydrindans in high yield. delta-(1-Cyclohexenyl) trifluoromethyl ketone 1a leads stereoselectively to 1-(trifluoromethyl)-1-hydroxy-DELTA-5,10-octalin 3a or 10-chloro-1-(trifluoromethyl)-1-hydroxydecalin 6a, depending on the choice of Lewis acid. gamma-(1-Cyclohexenyl) trifluoromethyl ketone 2a leads to a mixture of 9-chloro-1-(trifluoromethyl)-1-hydroxyhydrindans 10a and 11a. Similar reactions were performed successfully with the corresponding beta-keto esters 1b and 2b.

  DOI：

  10.1021/jo00020a021
• 作为产物：
  描述：

  2-甲基-4,4,4-三氟乙酰乙酸乙酯 、 (2-溴乙亚基)环己烷 在 六甲基磷酰三胺 、 sodium hydride 、 potassium iodide 作用下， 生成 2-(2-Cyclohexylidene-ethyl)-4,4,4-trifluoro-2-methyl-3-oxo-butyric acid ethyl ester
  参考文献：
  名称：

  Lewis acid induced ene cyclization of .omega.-olefinic trifluoromethyl ketones: access to bicyclic compounds bearing a trifluoromethyl group

  摘要：

  Lewis acid induced ene cyclization of omega-olefinic trifluoromethyl ketones provides (trifluoromethyl)decalins and (trifluoromethyl)hydrindans in high yield. delta-(1-Cyclohexenyl) trifluoromethyl ketone 1a leads stereoselectively to 1-(trifluoromethyl)-1-hydroxy-DELTA-5,10-octalin 3a or 10-chloro-1-(trifluoromethyl)-1-hydroxydecalin 6a, depending on the choice of Lewis acid. gamma-(1-Cyclohexenyl) trifluoromethyl ketone 2a leads to a mixture of 9-chloro-1-(trifluoromethyl)-1-hydroxyhydrindans 10a and 11a. Similar reactions were performed successfully with the corresponding beta-keto esters 1b and 2b.

  DOI：

  10.1021/jo00020a021

文献信息

• Lewis acid induced ene cyclization of .omega.-olefinic trifluoromethyl ketones: access to bicyclic compounds bearing a trifluoromethyl group
  作者：Ahmed Abouabdellah、Jean Pierre Begue、Daniele Bonnet-Delpon、Thierry Lequeux

  DOI：10.1021/jo00020a021

  日期：1991.9

  Lewis acid induced ene cyclization of omega-olefinic trifluoromethyl ketones provides (trifluoromethyl)decalins and (trifluoromethyl)hydrindans in high yield. delta-(1-Cyclohexenyl) trifluoromethyl ketone 1a leads stereoselectively to 1-(trifluoromethyl)-1-hydroxy-DELTA-5,10-octalin 3a or 10-chloro-1-(trifluoromethyl)-1-hydroxydecalin 6a, depending on the choice of Lewis acid. gamma-(1-Cyclohexenyl) trifluoromethyl ketone 2a leads to a mixture of 9-chloro-1-(trifluoromethyl)-1-hydroxyhydrindans 10a and 11a. Similar reactions were performed successfully with the corresponding beta-keto esters 1b and 2b.