1-(2,4-Dimethoxyphenyl)-2-ethenylazetidine | 1606993-61-6

• 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: 1-(2,4-Dimethoxyphenyl)-2-ethenylazetidine
• 英文别名: 1-(2,4-dimethoxyphenyl)-2-ethenylazetidine
• CAS: 1606993-61-6
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: XYQSBOGDPRFLOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,4-Dimethoxyphenyl)-2-ethenylazetidine 在 硫酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 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：

  2,4-二甲氧基苯胺 在 六甲基磷酰三胺 、 二异丁基氢化铝 、 碳酸氢钠 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 1-(2,4-Dimethoxyphenyl)-2-ethenylazetidine
  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

• Acid-Mediated Ring-Expansion Reaction of <i>N</i>-Aryl-2-vinylazetidines: Synthesis and Unanticipated Reactivity of Tetrahydrobenzazocines
  作者：Tomoaki Shimizu、Shunsuke Koya、Ryu Yamasaki、Yuichiro Mutoh、Isao Azumaya、Kosuke Katagiri、Shinichi Saito

  DOI：10.1021/jo500249c

  日期：2014.5.16

  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.