(E)-2-chloro-3-methyl-1,1,1-trifluoro-2-nonene | 141583-99-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-2-chloro-3-methyl-1,1,1-trifluoro-2-nonene
• 英文别名: (Z)-2-chloro-1,1,1-trifluoro-3-methylnon-2-ene
• CAS: 141583-99-5
• 化学式: C₁₀H₁₆ClF₃
• 分子量: 228.685
• InChiKey: LACDCBHGPLQLKI-HJWRWDBZSA-N

物化性质

• 沸点：
  213.4±35.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  仲辛酮 在 氢氟酸 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (E)-2-chloro-3-methyl-1,1,1-trifluoro-2-nonene
  参考文献：
  名称：

  A method for synthesis of fluorine compounds using abnormal Grignard reaction of halothane

  摘要：

  The reaction of 2-bromo-2-chloro-1,1,1-trifluoroethane (1) with 2-octanone (3a) in the presence of magnesium did not give 2-chloro-1,1,1-trifluoro-3-methyl-3-nonanol (4a) but 2-bromo-2-chloro-1,1,1-trifluoro-3-methyl-3-nonanol (5a) and 2-chloro-1,1-difluoro-3-methyl-1-nonen-3-ol (6a). This suggested that the primary Grignard reagent, 1-chloro-2,2,2-trifluoroethylmagnesium bromide (2), reacted with excess 1 rather than with the ketone 3a to give 1-bromo-1-chloro-2,2,2-trifluoroethylmagnesium bromide (8), which added to the ketone to give 5a. Detection of 1,1,1-trifluoro-2-chloroethane supported this mechanism. Compound 5a was formed preferentially at -53-degrees-C, and as the reaction mixture was warmed to 0-degrees-C, the amount of 5a decreased, while that of 6a increased. Therefore, compound 6a must be formed by reduction of 5a with excess magnesium. Treatment of 6a with hydrogen fluoride gave 2-chloro-1,1,1-trifluoro-3-methyl-2-nonene (9a). Cyclohexanone and acetophenone reacted similarly to give corresponding products.

  DOI：

  10.1021/jo00040a036

文献信息

• A method for synthesis of fluorine compounds using abnormal Grignard reaction of halothane
  作者：Toshiyuki Takagi、Atsushi Takesue、Mayumi Koyama、Akira Ando、Takuichi Miki、Itsumaro Kumadaki、Tomohiro Sato

  DOI：10.1021/jo00040a036

  日期：1992.7

  The reaction of 2-bromo-2-chloro-1,1,1-trifluoroethane (1) with 2-octanone (3a) in the presence of magnesium did not give 2-chloro-1,1,1-trifluoro-3-methyl-3-nonanol (4a) but 2-bromo-2-chloro-1,1,1-trifluoro-3-methyl-3-nonanol (5a) and 2-chloro-1,1-difluoro-3-methyl-1-nonen-3-ol (6a). This suggested that the primary Grignard reagent, 1-chloro-2,2,2-trifluoroethylmagnesium bromide (2), reacted with excess 1 rather than with the ketone 3a to give 1-bromo-1-chloro-2,2,2-trifluoroethylmagnesium bromide (8), which added to the ketone to give 5a. Detection of 1,1,1-trifluoro-2-chloroethane supported this mechanism. Compound 5a was formed preferentially at -53-degrees-C, and as the reaction mixture was warmed to 0-degrees-C, the amount of 5a decreased, while that of 6a increased. Therefore, compound 6a must be formed by reduction of 5a with excess magnesium. Treatment of 6a with hydrogen fluoride gave 2-chloro-1,1,1-trifluoro-3-methyl-2-nonene (9a). Cyclohexanone and acetophenone reacted similarly to give corresponding products.