2-(E)-benzylidene-6-trifluoroacetylcyclohexanone | 479499-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(E)-benzylidene-6-trifluoroacetylcyclohexanone
• 英文别名: 2-[(e)-Benzylidene]-6-(2,2,2-trifluoroacetyl)cyclohexanone；(2E)-2-benzylidene-6-(2,2,2-trifluoroacetyl)cyclohexan-1-one
• CAS: 479499-02-0
• 化学式: C₁₅H₁₃F₃O₂
• 分子量: 282.262
• InChiKey: SGWBMTTZEOAUDY-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(E)-benzylidene-6-trifluoroacetylcyclohexanone 在 三氟化硼乙醚 、 羟胺 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以58%的产率得到(7E)-7-benzylidene-3-(trifluoromethyl)-3,3a,4,5,6,7-hexahydro-2,1-benzisoxazol-3-ol
  参考文献：
  名称：

  2-(多氟酰基)环烷酮与羟胺的反应

  摘要：

  The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group. react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(200207)85:7<1960::aid-hlca1960>3.0.co;2-6
• 作为产物：
  描述：

  2-(三氟乙酰基)环己酮 、 苯甲醛 在 三氟化硼乙醚 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以95%的产率得到2-(E)-benzylidene-6-trifluoroacetylcyclohexanone
  参考文献：
  名称：

  摘要：

  Polyfluorinated 1,3-diketones containing carbocycles react with aldehydes under Lewis-acid catalysis and also with dimethylformamide-dimetylacetal without catalysis, yielding exclusively (E)-configured condensation products involving the methylene group of the carbocycle. Novel trifluoromethylated chromenes are prepared from 2-trifluoroacetylcycloalkanones and salicylaldehyde. The structures of two new compounds, 2-(E)-benzylidene-6-trifluoroacetylcyclohexanone and 4-trifluoroacetyl-2,3-dihydro-1H-xantene, are confirmed by X-ray structure analysis.

  DOI：

  10.1071/ch01027

文献信息

• ——
  作者：D. V. Sevenard、O. G. Khomutov、M. I. Kodess、K. I. Pashkevich、I. Loop、E. Lork、G.-V. Röschenthaler

  DOI：10.1071/ch01027

  日期：——

  Polyfluorinated 1,3-diketones containing carbocycles react with aldehydes under Lewis-acid catalysis and also with dimethylformamide-dimetylacetal without catalysis, yielding exclusively (E)-configured condensation products involving the methylene group of the carbocycle. Novel trifluoromethylated chromenes are prepared from 2-trifluoroacetylcycloalkanones and salicylaldehyde. The structures of two new compounds, 2-(E)-benzylidene-6-trifluoroacetylcyclohexanone and 4-trifluoroacetyl-2,3-dihydro-1H-xantene, are confirmed by X-ray structure analysis.
• Reaction of 2-(Polyfluoroacyl)cycloalkanones with Hydroxylamine
  作者：Dmitri V. Sevenard、Oleg G. Khomutov、Kazimir I. Pashkevich、Enno Lork、Gerd-Volker Röschenthaler

  DOI：10.1002/1522-2675(200207)85:7<1960::aid-hlca1960>3.0.co;2-6

  日期：2002.7

  The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group. react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis.