2-ethylideneamino-propionitrile | 167320-15-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-ethylideneamino-propionitrile
• CAS: 167320-15-2
• 化学式: C₅H₈N₂
• 分子量: 96.1319
• InChiKey: MROBOAMASDDHIY-XVNBXDOJSA-N

物化性质

• 沸点：
  172.4±32.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  7.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.15
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-ethylideneamino-propionitrile 在 Grubbs catalyst first generation 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,7-dimethyl-2,3,6,7-tetrahydroazepine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of N,N-Bis(3-butenyl)amines from 2-Azaallyl Dication Synthetic Equivalents and Conversion to 2,3,6,7-Tetrahydroazepines by Ring-Closing Metathesis

  摘要：

  [GRAPHICS]N,N-Bis(3-butenyl)amines can be prepared by the double allylation of either (2-azaallyl)stannanes or (2-azaallyl)nitriles, both of which thereby act as synthetic equivalents to amine alpha,alpha'-dications (2-azaallyl dications). Allylmagnesium bromide is the reagent of choice for the double allylation of both substrates, although allyllithium also effects the double allylation of (2-azaallyl)nitriles. Ring-closing metathesis can be performed on the N-protected amines, or with in situ protonation, on the free amines to provide 2,3,6,7-tetrahydroazepines. (2-Azaallyl)nitriles can also be monoallylated to provide N-(3-butenyl)-aminonitriles, whereas the double allylation of (2-azaallyl)stannanes cannot be stopped at monoallylation. (2-Azaallyl)silanes undergo monoallylation to give N-(3-butenyl)aminosilanes but do not undergo double allylation.

  DOI：

  10.1021/jo060173s
• 作为产物：
  描述：

  乙醛 、 2-氨基丙腈 在 4 A molecular sieve 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以64%的产率得到2-ethylideneamino-propionitrile
  参考文献：
  名称：

  Synthesis of N,N-Bis(3-butenyl)amines from 2-Azaallyl Dication Synthetic Equivalents and Conversion to 2,3,6,7-Tetrahydroazepines by Ring-Closing Metathesis

  摘要：

  [GRAPHICS]N,N-Bis(3-butenyl)amines can be prepared by the double allylation of either (2-azaallyl)stannanes or (2-azaallyl)nitriles, both of which thereby act as synthetic equivalents to amine alpha,alpha'-dications (2-azaallyl dications). Allylmagnesium bromide is the reagent of choice for the double allylation of both substrates, although allyllithium also effects the double allylation of (2-azaallyl)nitriles. Ring-closing metathesis can be performed on the N-protected amines, or with in situ protonation, on the free amines to provide 2,3,6,7-tetrahydroazepines. (2-Azaallyl)nitriles can also be monoallylated to provide N-(3-butenyl)-aminonitriles, whereas the double allylation of (2-azaallyl)stannanes cannot be stopped at monoallylation. (2-Azaallyl)silanes undergo monoallylation to give N-(3-butenyl)aminosilanes but do not undergo double allylation.

  DOI：

  10.1021/jo060173s