1-(3-phenoxypropyl)azepane hydrochloride | 1402604-28-7

• 英文名称: 1-(3-phenoxypropyl)azepane hydrochloride
• CAS: 1402604-28-7
• 化学式: C₁₅H₂₃NO*ClH
• 分子量: 269.815
• InChiKey: ZRJOMJDLULEROC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(3-phenoxypropyl)azepane hydrochloride 、 4-氯丁酰氯 在 aluminum (III) chloride 、 三乙基硅烷 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.17h， 以962 g的产率得到1-(3-(4-(4-chlorobutyl)phenoxy)propyl)azepane hydrochloride
  参考文献：
  名称：

  Development of a Selective Friedel–Crafts Alkylation Surrogate: Safe Operating Conditions through Mechanistic Understanding

  摘要：

  This article describes a selective one-pot, Friedel-Crafts acylation/ketone reduction protocol, effectively a surrogate for the Friedel-Crafts alkylation reaction with a primary alkyl halide. A potentially dangerous failure mode was identified, resulting in the uncontrolled evolution of hydrogen. A series of mechanistic experiments, including analysis by Al-27 NMR, was undertaken, and the reaction mechanism elucidated. Finally, the use of React IR to ensure real-time reaction safety was demonstrated.

  DOI：

  10.1021/op300257z
• 作为产物：
  描述：

  环己亚胺 、 3-苯氧基溴丙烷 在 potassium carbonate 、 丁二酸酐 、 盐酸 作用下， 以 甲醇 、 甲基叔丁基醚 、 水 、 异丙醇 为溶剂， 反应 19.17h， 以90%的产率得到1-(3-phenoxypropyl)azepane hydrochloride
  参考文献：
  名称：

  Development of a Selective Friedel–Crafts Alkylation Surrogate: Safe Operating Conditions through Mechanistic Understanding

  摘要：

  This article describes a selective one-pot, Friedel-Crafts acylation/ketone reduction protocol, effectively a surrogate for the Friedel-Crafts alkylation reaction with a primary alkyl halide. A potentially dangerous failure mode was identified, resulting in the uncontrolled evolution of hydrogen. A series of mechanistic experiments, including analysis by Al-27 NMR, was undertaken, and the reaction mechanism elucidated. Finally, the use of React IR to ensure real-time reaction safety was demonstrated.

  DOI：

  10.1021/op300257z