2-(2-amino-5-chloropyridin-3-yl)propan-2-ol | 213666-97-8

• 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-(2-amino-5-chloropyridin-3-yl)propan-2-ol
• CAS: 213666-97-8
• 化学式: C₈H₁₁ClN₂O
• 分子量: 186.641
• InChiKey: AJNNZXOSKHZOTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-amino-5-chloropyridin-3-yl)propan-2-ol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 (+/-)-(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：

  甲基氯化镁 、 2-氨基-5-氯烟酸甲酯 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-(2-amino-5-chloropyridin-3-yl)propan-2-ol
  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

• PROCESS FOR THE MANUFACTURE OF PHARMACEUTICALLY ACTIVE COMPOUNDS
  申请人：Hildbrand Stefan

  公开号：US20110028511A1

  公开（公告）日：2011-02-03

  According to the present invention there are provided novel processes for the manufacture of the compound of formula 1 as well as novel synthesis routes for key intermediates used in those processes.

  根据本发明提供了制备化合物1的新工艺，以及用于这些工艺中的关键中间体的新合成路线。
• US8329724B2
  申请人：——

  公开号：US8329724B2

  公开（公告）日：2012-12-11
• [EN] PROCESS FOR THE MANUFACTURE OF PHARMACEUTICALLY ACTIVE COMPOUNDS<br/>[FR] PROCÉDÉ DE FABRICATION DE COMPOSÉS PHARMACEUTIQUEMENT ACTIFS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011015522A2

  公开（公告）日：2011-02-10

  According to the present invention there are provided novel processes for the manufacture of the compound of formula (1) as well as novel synthesis routes for key intermediates used in those processes.
• 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).