N¹-methyl-N⁴-(3-azidopropyl)-1-methyl-1,4-diaminobutane | 148759-48-2

• 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: N¹-methyl-N⁴-(3-azidopropyl)-1-methyl-1,4-diaminobutane
• 英文别名: 1-N-(3-azidopropyl)-4-N-methylpentane-1,4-diamine
• CAS: 148759-48-2
• 化学式: C₉H₂₁N₅
• 分子量: 199.299
• InChiKey: DMFWZKJLTDZFOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹-methyl-N⁴-(3-azidopropyl)-1-methyl-1,4-diaminobutane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以83%的产率得到N¹-methyl-N⁴-(3-aminopropyl)-1-methyl-1,4-diaminobutane
  参考文献：
  名称：

  Aliphatic amino azides as key building blocks for efficient polyamine syntheses

  摘要：

  New routes to open-chain polyamines have been developed using aliphatic amino azides as common precursors for the construction of the carbon-nitrogen framework. These alpha,omega-diaminoalkane synthetic equivalents were combined with (omega-halogenoalkyl)dichloroboranes to extend the polyamine chain from the azido moiety. An extension from the free amino group can also be achieved via a Michael type addition with acrylonitrile or a reductive amination with a gamma-azido ketone. Further transformations led to a large variety of regioselectively C- or (and) N-substituted polyamines.

  DOI：

  10.1021/jo00066a028
• 作为产物：
  描述：

  N¹-methyl-N⁴-(3-bromopropyl)-1-methyl-1,4-diaminobutane dihydrochloride 在 sodium azide 作用下， 以 水 为溶剂， 反应 15.0h， 以90%的产率得到N¹-methyl-N⁴-(3-azidopropyl)-1-methyl-1,4-diaminobutane
  参考文献：
  名称：

  Aliphatic amino azides as key building blocks for efficient polyamine syntheses

  摘要：

  New routes to open-chain polyamines have been developed using aliphatic amino azides as common precursors for the construction of the carbon-nitrogen framework. These alpha,omega-diaminoalkane synthetic equivalents were combined with (omega-halogenoalkyl)dichloroboranes to extend the polyamine chain from the azido moiety. An extension from the free amino group can also be achieved via a Michael type addition with acrylonitrile or a reductive amination with a gamma-azido ketone. Further transformations led to a large variety of regioselectively C- or (and) N-substituted polyamines.

  DOI：

  10.1021/jo00066a028