(S)-2-Azido-3,3-dimethyl-butyronitrile | 175790-73-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-2-Azido-3,3-dimethyl-butyronitrile
• 英文别名: (2S)-2-azido-3,3-dimethylbutanenitrile
• CAS: 175790-73-5
• 化学式: C₆H₁₀N₄
• 分子量: 138.172
• InChiKey: LKMHZIXHNWCRTA-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Azido-3,3-dimethyl-butyronitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (+)-3,3-Dimethyl-1,2-diamin
  参考文献：
  名称：

  A convenient synthesis of (S)-2-Azidonitriles, (S)-2-aminonitriles and (S)-1,2-diamines

  摘要：

  (S)-2-Azidonitriles (S)-4 are easily accessible from (R)-2-(sulfonyloxy)nitriles (R)-2 by nucleophilic substitution with alkali azides 3 under complete inversion of configuration. The azidonitriles (S)-4 can be converted by catalytic hydrogenation into (S)-2-aminonitriles (S)-8 and by hydrogenation using LiAlH4 into (S)-1, 2-diaminoalkanes (S)-9, respectively, both, (S)-8 and (S)-9, isolated as hydrochlorides. Hydrolysis of the aminonitrile hydrochlorides (S)-8 HCl in a saturated solution of HC1 in alcohol gives (S)-2-amino carboxamide hydrochlorides(S)-10 . HCl with enantiomeric excesses >99% after recrystallization.

  DOI：

  10.1016/0957-4166(96)00044-4
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (R)-1-cyano-2,2-dimethyl-propyl ester 在 叠氮化四丁基铵 作用下， 以 苯 为溶剂， 反应 48.0h， 以67%的产率得到(S)-2-Azido-3,3-dimethyl-butyronitrile
  参考文献：
  名称：

  A convenient synthesis of (S)-2-Azidonitriles, (S)-2-aminonitriles and (S)-1,2-diamines

  摘要：

  (S)-2-Azidonitriles (S)-4 are easily accessible from (R)-2-(sulfonyloxy)nitriles (R)-2 by nucleophilic substitution with alkali azides 3 under complete inversion of configuration. The azidonitriles (S)-4 can be converted by catalytic hydrogenation into (S)-2-aminonitriles (S)-8 and by hydrogenation using LiAlH4 into (S)-1, 2-diaminoalkanes (S)-9, respectively, both, (S)-8 and (S)-9, isolated as hydrochlorides. Hydrolysis of the aminonitrile hydrochlorides (S)-8 HCl in a saturated solution of HC1 in alcohol gives (S)-2-amino carboxamide hydrochlorides(S)-10 . HCl with enantiomeric excesses >99% after recrystallization.

  DOI：

  10.1016/0957-4166(96)00044-4