N-methyl-N-(naphthalen-1-yl)trifluoropropanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-methyl-N-(naphthalen-1-yl)trifluoropropanamide
• 英文别名: 3,3,3-trifluoro-N-methyl-N-naphthalen-1-ylpropanamide
• 化学式: C₁₄H₁₂F₃NO
• 分子量: 267.251
• InChiKey: GNXDLFMYECGETE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(naphthalen-1-yl)trifluoropropanamide 在 亚硝酸特丁酯 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以67%的产率得到methyl(naphthalen-1-yl)carbamoyl cyanide
  参考文献：
  名称：

  Transition-Metal-Free Conversion of Trifluoropropanamides into Cyanoformamides through C–CF₃ Bond Cleavage and Nitrogenation

  摘要：

  w A new transition-metal-free transformation of trifluoropropanamides into cyanoformamides through a sequence of C-CF3 bond cleavage and nitrogenation using tert-butyl nitrite as the nitrogen source,is described. The method features direct detrifluoromethylation, broad substrate scopes, and excellent selectivity control, representing a new shortcut for constructing the nitrile group involving C-CF3 sigma-bond cleavage.

  DOI：

  10.1021/acs.joc.7b00626
• 作为产物：
  描述：

  3,3,3-三氟丙酸 、 N-甲基-1-萘胺 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-methyl-N-(naphthalen-1-yl)trifluoropropanamide
  参考文献：
  名称：

  Transition-Metal-Free Conversion of Trifluoropropanamides into Cyanoformamides through C–CF₃ Bond Cleavage and Nitrogenation

  摘要：

  w A new transition-metal-free transformation of trifluoropropanamides into cyanoformamides through a sequence of C-CF3 bond cleavage and nitrogenation using tert-butyl nitrite as the nitrogen source,is described. The method features direct detrifluoromethylation, broad substrate scopes, and excellent selectivity control, representing a new shortcut for constructing the nitrile group involving C-CF3 sigma-bond cleavage.

  DOI：

  10.1021/acs.joc.7b00626

文献信息

• Transition-Metal-Free Conversion of Trifluoropropanamides into Cyanoformamides through C–CF₃ Bond Cleavage and Nitrogenation
  作者：Fang Wang、Tao Zhang、Hai-Yong Tu、Xing-Guo Zhang

  DOI：10.1021/acs.joc.7b00626

  日期：2017.5.19

  w A new transition-metal-free transformation of trifluoropropanamides into cyanoformamides through a sequence of C-CF3 bond cleavage and nitrogenation using tert-butyl nitrite as the nitrogen source,is described. The method features direct detrifluoromethylation, broad substrate scopes, and excellent selectivity control, representing a new shortcut for constructing the nitrile group involving C-CF3 sigma-bond cleavage.