Ethyl 4,4,4-trifluoro-2-methyl-2-<(1-cyclohexenyl)methyl>-3-oxobutanoate | 136425-06-4

• 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: Ethyl 4,4,4-trifluoro-2-methyl-2-<(1-cyclohexenyl)methyl>-3-oxobutanoate
• 英文别名: Ethyl 2-(cyclohexen-1-ylmethyl)-4,4,4-trifluoro-2-methyl-3-oxobutanoate
• CAS: 136425-06-4
• 化学式: C₁₄H₁₉F₃O₃
• 分子量: 292.298
• InChiKey: VXZQZTJCQLMFPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4,4,4-trifluoro-2-methyl-2-<(1-cyclohexenyl)methyl>-3-oxobutanoate 在 吡啶 、 氢氧化钾 、 四氯化钛 、 苯磺酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-(Trifluoromethyl)-2-methyl-4,5,6,7-tetrahydroindene
  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 、 1-溴甲基环已烯 在 六甲基磷酰三胺 、 sodium hydride 、 potassium iodide 作用下， 生成 Ethyl 4,4,4-trifluoro-2-methyl-2-<(1-cyclohexenyl)methyl>-3-oxobutanoate
  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

• Perfluoroalkyl ketones and perfluoroalkyl enol ethers from perfluoroalkyl esters by Wittig reaction
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Gérard Née、Shen-Weng Wu

  DOI：10.1016/s0022-1139(00)83789-6

  日期：1991.9
• 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.