N-(4-trifluoromethylphenyl)-2-vinylazetidine | 1606993-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: N-(4-trifluoromethylphenyl)-2-vinylazetidine
• 英文别名: 2-Ethenyl-1-[4-(trifluoromethyl)phenyl]azetidine；2-ethenyl-1-[4-(trifluoromethyl)phenyl]azetidine
• CAS: 1606993-64-9
• 化学式: C₁₂H₁₂F₃N
• 分子量: 227.229
• InChiKey: FFBILOIYQUQWKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 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：
  3.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-trifluoromethylphenyl)-2-vinylazetidine 在 硫酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.17h， 生成
  参考文献：
  名称：

  Acid-Mediated Ring-Expansion Reaction of N-Aryl-2-vinylazetidines: Synthesis and Unanticipated Reactivity of Tetrahydrobenzazocines

  摘要：

  The aza-Clasen rearrangement of N-aryl-2-vinylazetidines has been explored. N-Aryl-2-vinylazetidines were transformed to corresponding tetrahydrobenzazocines in good yields. Unexpectedly, the tetrahydrobenzazocine was unstable and readily isomerized to vinyltetrahydroquinoline in the presence of acid. The mechanism of this ring contraction was studied in detail.

  DOI：

  10.1021/jo500249c
• 作为产物：
  描述：

  对三氟甲基苯胺 在 六甲基磷酰三胺 、 二异丁基氢化铝 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 N-(4-trifluoromethylphenyl)-2-vinylazetidine
  参考文献：
  名称：

  Acid-Mediated Ring-Expansion Reaction of N-Aryl-2-vinylazetidines: Synthesis and Unanticipated Reactivity of Tetrahydrobenzazocines

  摘要：

  The aza-Clasen rearrangement of N-aryl-2-vinylazetidines has been explored. N-Aryl-2-vinylazetidines were transformed to corresponding tetrahydrobenzazocines in good yields. Unexpectedly, the tetrahydrobenzazocine was unstable and readily isomerized to vinyltetrahydroquinoline in the presence of acid. The mechanism of this ring contraction was studied in detail.

  DOI：

  10.1021/jo500249c

文献信息

• Synthesis of Tricyclic Benzazocines by Aza-Prins Reaction
  作者：Tomohiro Katamura、Tomoaki Shimizu、Yuichiro Mutoh、Shinichi Saito

  DOI：10.1021/acs.orglett.6b03577

  日期：2017.1.6

  The aza-Prins reaction of 3-vinyltetrahydroquinolines with aldehydes proceeded smoothly in the presence of hydrogen halides, and the tricyclic benzazocine derivatives were isolated in good to high yields. The reaction would proceed through the formation and cyclization of the iminium ion intermediate.

  3-乙烯基四氢喹啉与醛的aza-Prins反应在卤化氢存在下进行得很顺利，并且以高收率或高收率分离出了三环苯并偶氮衍生物。反应将通过亚胺离子中间体的形成和环化进行。