N-1-naphthyl-2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazide | 143681-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-1-naphthyl-2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazide
• 英文别名: 2,2,2-trifluoro-N'-naphthalen-1-yl-N-(propan-2-ylideneamino)ethanimidamide
• CAS: 143681-48-5
• 化学式: C₁₅H₁₄F₃N₃
• 分子量: 293.291
• InChiKey: UGFZOKPARHVFQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-1-naphthyl-2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazide 在 次氯酸叔丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以76%的产率得到3-(trifluoromethyl)naphtho-1,2,4-triazine
  参考文献：
  名称：

  N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides as synthetic blocks for trifluoromethylated nitrogen heterocycles: syntheses and oxidative cyclizations

  摘要：

  N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides have been prepared and allowed to react with tert-butyl hypochlorite in CH2Cl2. N-Aryl-, N-alkyl-, and N-(methoxycarbonyl)amidrazones 2-4 undergo three types of cyclizations via the initially formed N-chloro intermediates leading to 3-(trifluoromethyl)-1,2,4-benzotriazines, 5, 3-(trifluoromethyl)-5-alkyltriazoles 8 and 9, and 3-chloro-3-(trifluoromethyl)-4-N-(methoxycarbonyl)-5,5-dimethyltriazoline (11), respectively. Reaction mechanisms for the cyclizations are discussed.

  DOI：

  10.1021/jo00048a042
• 作为产物：
  描述：

  2,2,2-trifluoro-N-naphthalen-1-ylethanimidoyl chloride 、 二丙酮腙 在 一水合肼 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以72%的产率得到N-1-naphthyl-2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazide
  参考文献：
  名称：

  N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides as synthetic blocks for trifluoromethylated nitrogen heterocycles: syntheses and oxidative cyclizations

  摘要：

  N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides have been prepared and allowed to react with tert-butyl hypochlorite in CH2Cl2. N-Aryl-, N-alkyl-, and N-(methoxycarbonyl)amidrazones 2-4 undergo three types of cyclizations via the initially formed N-chloro intermediates leading to 3-(trifluoromethyl)-1,2,4-benzotriazines, 5, 3-(trifluoromethyl)-5-alkyltriazoles 8 and 9, and 3-chloro-3-(trifluoromethyl)-4-N-(methoxycarbonyl)-5,5-dimethyltriazoline (11), respectively. Reaction mechanisms for the cyclizations are discussed.

  DOI：

  10.1021/jo00048a042

文献信息

• N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides as synthetic blocks for trifluoromethylated nitrogen heterocycles: syntheses and oxidative cyclizations
  作者：Kenji Uneyama、Kouji Sugimoto

  DOI：10.1021/jo00048a042

  日期：1992.10

  N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides have been prepared and allowed to react with tert-butyl hypochlorite in CH2Cl2. N-Aryl-, N-alkyl-, and N-(methoxycarbonyl)amidrazones 2-4 undergo three types of cyclizations via the initially formed N-chloro intermediates leading to 3-(trifluoromethyl)-1,2,4-benzotriazines, 5, 3-(trifluoromethyl)-5-alkyltriazoles 8 and 9, and 3-chloro-3-(trifluoromethyl)-4-N-(methoxycarbonyl)-5,5-dimethyltriazoline (11), respectively. Reaction mechanisms for the cyclizations are discussed.