2-amino-5-chloro-3-isopropenylpyridine | 213666-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-5-chloro-3-isopropenylpyridine
• 英文别名: 5-Chloro-3-prop-1-en-2-ylpyridin-2-amine
• CAS: 213666-99-0
• 化学式: C₈H₉ClN₂
• mdl: MFCD18803284
• 分子量: 168.626
• InChiKey: FFWCDZSMMMXGSB-UHFFFAOYSA-N

物化性质

• 沸点：
  272.0±40.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基-4-哌啶酮 、 2-amino-5-chloro-3-isopropenylpyridine 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以92%的产率得到(+/-)-(4aRS,5aRS,10aRS)-7-chloro-3,5a-dimethyl-1,2,3,4,4a,5,5a,10-octahydropyrido<4'',3'':2',3'>cyclobuta<1',2':4,5>pyrrolo<2,3-b>pyridine
  参考文献：
  名称：

  Novel Complex N-Heterocycles via Intramolecular 1,5-Electrocyclizations: 1,2,3,4,4a,5,5a,10-Octahydropyrido-[4",3":2',3']cyclobuta[1',2':4,5]pyrrolo[2,3-b]pyridines

  摘要：

  The synthesis of 2-amino-3-isopropenylpyridine (5) and 2-amino-5-chloro-3-isopropenylpyridine (6) and their toluenesulfonic acid catalyzed reactions in refluxing toluene with some 1-substituted piperidin-4-ones are described. The toluenesulfonic acid catalyzed reaction of the pyridine derivatives (5) and (6) with 1-benzyl-, 1-benzoyl- and 1-methylpiperidin-4-one lead to novel pyrrolo[2,3-b]-pyridines (7-12) in good to excellent yields in diastereoisomeric pure form (Scheme 2, Table 1). An intramolecular 1,5-electrocyclization of the dipolar reactive intermediate (13) as a key step (Scheme 3) is proposed for the formation of the compounds (7-12).

  DOI：

  10.3987/com-98-8190
• 作为产物：
  描述：

  2-氨基-5-氯烟酸甲酯 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-amino-5-chloro-3-isopropenylpyridine
  参考文献：
  名称：

  Novel Complex N-Heterocycles via Intramolecular 1,5-Electrocyclizations: 1,2,3,4,4a,5,5a,10-Octahydropyrido-[4",3":2',3']cyclobuta[1',2':4,5]pyrrolo[2,3-b]pyridines

  摘要：

  The synthesis of 2-amino-3-isopropenylpyridine (5) and 2-amino-5-chloro-3-isopropenylpyridine (6) and their toluenesulfonic acid catalyzed reactions in refluxing toluene with some 1-substituted piperidin-4-ones are described. The toluenesulfonic acid catalyzed reaction of the pyridine derivatives (5) and (6) with 1-benzyl-, 1-benzoyl- and 1-methylpiperidin-4-one lead to novel pyrrolo[2,3-b]-pyridines (7-12) in good to excellent yields in diastereoisomeric pure form (Scheme 2, Table 1). An intramolecular 1,5-electrocyclization of the dipolar reactive intermediate (13) as a key step (Scheme 3) is proposed for the formation of the compounds (7-12).

  DOI：

  10.3987/com-98-8190

文献信息

• Novel Complex N-Heterocycles via Intramolecular 1,5-Electrocyclizations: 1,2,3,4,4a,5,5a,10-Octahydropyrido-[4",3":2',3']cyclobuta[1',2':4,5]pyrrolo[2,3-b]pyridines
  作者：Harald Walter、Carsten Sundermann

  DOI：10.3987/com-98-8190

  日期：——

  The synthesis of 2-amino-3-isopropenylpyridine (5) and 2-amino-5-chloro-3-isopropenylpyridine (6) and their toluenesulfonic acid catalyzed reactions in refluxing toluene with some 1-substituted piperidin-4-ones are described. The toluenesulfonic acid catalyzed reaction of the pyridine derivatives (5) and (6) with 1-benzyl-, 1-benzoyl- and 1-methylpiperidin-4-one lead to novel pyrrolo[2,3-b]-pyridines (7-12) in good to excellent yields in diastereoisomeric pure form (Scheme 2, Table 1). An intramolecular 1,5-electrocyclization of the dipolar reactive intermediate (13) as a key step (Scheme 3) is proposed for the formation of the compounds (7-12).