N-(1-allyl-cyclohexyl)-N-(1-methylbut-3-enyl)amine | 342775-58-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1-allyl-cyclohexyl)-N-(1-methylbut-3-enyl)amine
• 英文别名: N-pent-4-en-2-yl-1-prop-2-enylcyclohexan-1-amine
• CAS: 342775-58-0
• 化学式: C₁₄H₂₅N
• 分子量: 207.359
• InChiKey: FKHQOTRIQDCWIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-allyl-cyclohexyl)-N-(1-methylbut-3-enyl)amine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以62%的产率得到8-methyl-7-aza-spiro[5.6]dodec-10-ene
  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：

  1-氨基环己烷甲腈 在 正丁基锂 、 4 A molecular sieve 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 20.0h， 生成 N-(1-allyl-cyclohexyl)-N-(1-methylbut-3-enyl)amine
  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

文献信息

• Double Allylation Reactions of (2-Azaallyl)stannanes:  Synthesis of <i>N,N</i>-Bis(3-butenyl)amines and Their Conversion to 2,3,6,7-Tetrahydroazepines via Ring-Closing Metathesis
  作者：William H. Pearson、Aaron Aponick

  DOI：10.1021/ol015711w

  日期：2001.5.1

  [GRAPHICS]Treatment of (2-azaallyl)stannanes (i) with 2.2 equiv of allylmagnesium bromide afforded good yields of N,N-bis(3-butenyl)amines derivatives (ii), which were subjected to ring-closing metathesis ts afford 2,3,6,7 tetrahydroazepines (iii), Thus, (2-azaallyl)stannanes are the synthetic equivalents of amine alpha,alpha ' -dications.