2-ethoxy-5,5,5-trifluoro-4,4-dihydroxypentanenitrile | 303767-87-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2-ethoxy-5,5,5-trifluoro-4,4-dihydroxypentanenitrile
• CAS: 303767-87-5
• 化学式: C₇H₁₀F₃NO₃
• 分子量: 213.157
• InChiKey: DLVGSORJMCNTTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-ethoxy-5,5,5-trifluoro-4,4-dihydroxypentanenitrile 在 phosphorus pentoxide 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以81%的产率得到2-ethoxy-5,5,5-trifluoro-4-oxopentanenitrile
  参考文献：
  名称：

  Regioselective Addition of Trimethylsilyl Cyanide to β-Alkoxyvinyl Alkyl Ketones

  摘要：

  The 1,2- and 1,4-addition reactions of trimethylsilyl cyanide to alkyl vinyl ketones were studied. Regioselectivity of this reaction depends on the structure of alkyl vinyl ketones, the reaction temperature and the nature of catalyst. The presence of alkoxy group in beta-position of alpha,beta-enone is the important condition for realization of 1,4-addition. Ambient temperature (25 degrees C) or base catalyst (NEt3) directed the reaction predominantly into 1,2-addition; higher temperature, electrophilic catalyst (I-2) and bulky alkyl substituents near the carbonyl group directed the reaction in 1,4-addition route. Hydrolysis of 1,4-adducts yields saturated fluorine-containing ketones containing CN- and ethoxy groups at the beta-position. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)00603-7
• 作为产物：
  描述：

  1-乙氧基-3-三氟甲基-1,3-丁二烯 在 水 、 碘 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 2-ethoxy-5,5,5-trifluoro-4,4-dihydroxypentanenitrile
  参考文献：
  名称：

  Regioselective Addition of Trimethylsilyl Cyanide to β-Alkoxyvinyl Alkyl Ketones

  摘要：

  The 1,2- and 1,4-addition reactions of trimethylsilyl cyanide to alkyl vinyl ketones were studied. Regioselectivity of this reaction depends on the structure of alkyl vinyl ketones, the reaction temperature and the nature of catalyst. The presence of alkoxy group in beta-position of alpha,beta-enone is the important condition for realization of 1,4-addition. Ambient temperature (25 degrees C) or base catalyst (NEt3) directed the reaction predominantly into 1,2-addition; higher temperature, electrophilic catalyst (I-2) and bulky alkyl substituents near the carbonyl group directed the reaction in 1,4-addition route. Hydrolysis of 1,4-adducts yields saturated fluorine-containing ketones containing CN- and ethoxy groups at the beta-position. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)00603-7

文献信息

• Regioselective Addition of Trimethylsilyl Cyanide to β-Alkoxyvinyl Alkyl Ketones
  作者：Igor S. Kruchok、Igor I. Gerus、Valery P. Kukhar

  DOI：10.1016/s0040-4020(00)00603-7

  日期：2000.8

  The 1,2- and 1,4-addition reactions of trimethylsilyl cyanide to alkyl vinyl ketones were studied. Regioselectivity of this reaction depends on the structure of alkyl vinyl ketones, the reaction temperature and the nature of catalyst. The presence of alkoxy group in beta-position of alpha,beta-enone is the important condition for realization of 1,4-addition. Ambient temperature (25 degrees C) or base catalyst (NEt3) directed the reaction predominantly into 1,2-addition; higher temperature, electrophilic catalyst (I-2) and bulky alkyl substituents near the carbonyl group directed the reaction in 1,4-addition route. Hydrolysis of 1,4-adducts yields saturated fluorine-containing ketones containing CN- and ethoxy groups at the beta-position. (C) 2000 Published by Elsevier Science Ltd.