(S)-3-dichloroaminomethyl-5-methylhexanoic acid | 1402746-76-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-dichloroaminomethyl-5-methylhexanoic acid
• CAS: 1402746-76-2
• 化学式: C₈H₁₅Cl₂NO₂
• 分子量: 228.119
• InChiKey: ODAJXPFDYRPRET-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-3-dichloroaminomethyl-5-methylhexanoic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以1.65 g的产率得到(3S)-3-氰基-5-甲基己酸
  参考文献：
  名称：

  From pregabalin to rac-3-cyano-5-methylhexanoic acid: an easy conversion which valorizes waste pregabalin enantiomer

  摘要：

  (S)-(+)-3-Aminomethyl-5-methylhexanoic acid (pregabalin) was converted in one-pot to (S)-(-)-3-cyano-5-methylhexanoic acid (pregabalin nitrile) by N-dichlorination and double dehydrochlorination. The (S) beta-cyanoacid was racemized under mild conditions by treatment with a base. This very simple and efficient procedure, applied to (R)-(-)-3-aminomethyl-5-methylhexanoic acid, would enable the recycling of the undesired enantiomer of pregabalin, an anticonvulsant drug manufactured by the synthesis of roc-3-aminomethyl-5-methylhexanoic acid and subsequent classical resolution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.128
• 作为产物：
  描述：

  普瑞巴林 在 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-3-dichloroaminomethyl-5-methylhexanoic acid
  参考文献：
  名称：

  From pregabalin to rac-3-cyano-5-methylhexanoic acid: an easy conversion which valorizes waste pregabalin enantiomer

  摘要：

  (S)-(+)-3-Aminomethyl-5-methylhexanoic acid (pregabalin) was converted in one-pot to (S)-(-)-3-cyano-5-methylhexanoic acid (pregabalin nitrile) by N-dichlorination and double dehydrochlorination. The (S) beta-cyanoacid was racemized under mild conditions by treatment with a base. This very simple and efficient procedure, applied to (R)-(-)-3-aminomethyl-5-methylhexanoic acid, would enable the recycling of the undesired enantiomer of pregabalin, an anticonvulsant drug manufactured by the synthesis of roc-3-aminomethyl-5-methylhexanoic acid and subsequent classical resolution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.128