(S)-4-amino-4-(pyridin-3-yl)butan-1-ol | 231288-23-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-4-amino-4-(pyridin-3-yl)butan-1-ol
• 英文别名: (S)-4-amino-4-(3-pyridyl)-1-butanol；(4S)-4-amino-4-pyridin-3-ylbutan-1-ol
• CAS: 231288-23-6
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: KGHCMNWTCFZSDK-VIFPVBQESA-N

物化性质

• 沸点：
  333.1±37.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (S)-4-amino-4-(pyridin-3-yl)butan-1-ol 、 硫酸二甲酯 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以92.2 %的产率得到(S)-4-(methylamino)-4-(3-pyridyl)-1-butanol
  参考文献：
  名称：

  Method for synthesizing (S)-nicotine and intermediate thereof

  摘要：

  Disclosed is a method for synthesizing (S)-nicotine and an intermediate thereof, which belongs to the field of synthesizing a heterocyclic compound. A chiral amino group is introduced into 4-hydroxy-1-(3-pyridyl)-1-butanone by transaminase chiral catalysis in the presence of an amino donor to obtain (S)-4-amino-4-(3-pyridyl)-1-butanol. An N-methylation reaction is performed on (S)-4-amino-4-(3-pyridyl)-1-butanol with a methylating agent to obtain (S)-4-(methylamino)-4-(3-pyridyl)-1-butanol. The intermediate is reacted with an acylating agent or a halogenating agent to convert an alcoholic hydroxyl group into a sulfonate group or a halogen. Finally, a ring closure reaction is performed to obtain (S)-nicotine in an alkaline condition. The raw materials are cheap and readily available, the reaction conditions are mild, the operation is simple, and the cost is low. A single configuration of (S)-nicotine can be obtained with high selectivity, and thus the method is particularly suitable for industrial production of (S)-nicotine.

  公开号：

  US11884644B1
• 作为产物：
  描述：

  4-羟基-1-(3-吡啶基)-1-丁酮 在 盐酸 、 磷酸吡哆醛 、 异丙胺 作用下， 以 aq. phosphate buffer 、 水 为溶剂， 以91 %的产率得到(S)-4-amino-4-(pyridin-3-yl)butan-1-ol
  参考文献：
  名称：

  Method for synthesizing (S)-nicotine and intermediate thereof

  摘要：

  Disclosed is a method for synthesizing (S)-nicotine and an intermediate thereof, which belongs to the field of synthesizing a heterocyclic compound. A chiral amino group is introduced into 4-hydroxy-1-(3-pyridyl)-1-butanone by transaminase chiral catalysis in the presence of an amino donor to obtain (S)-4-amino-4-(3-pyridyl)-1-butanol. An N-methylation reaction is performed on (S)-4-amino-4-(3-pyridyl)-1-butanol with a methylating agent to obtain (S)-4-(methylamino)-4-(3-pyridyl)-1-butanol. The intermediate is reacted with an acylating agent or a halogenating agent to convert an alcoholic hydroxyl group into a sulfonate group or a halogen. Finally, a ring closure reaction is performed to obtain (S)-nicotine in an alkaline condition. The raw materials are cheap and readily available, the reaction conditions are mild, the operation is simple, and the cost is low. A single configuration of (S)-nicotine can be obtained with high selectivity, and thus the method is particularly suitable for industrial production of (S)-nicotine.

  公开号：

  US11884644B1