N-(2-Methyl-1-propen-1-yl)-N-2-propen-1-ylcyclohexanemethanamine | 137496-51-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-Methyl-1-propen-1-yl)-N-2-propen-1-ylcyclohexanemethanamine
• 英文别名: N-(cyclohexylmethyl)-2-methyl-N-prop-2-enylprop-1-en-1-amine
• CAS: 137496-51-6
• 化学式: C₁₄H₂₅N
• 分子量: 207.359
• InChiKey: CBNCQRHRMIVLEN-UHFFFAOYSA-N

物化性质

• 沸点：
  292.1±19.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-Methyl-1-propen-1-yl)-N-2-propen-1-ylcyclohexanemethanamine 在 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 Cyclohexylmethyl-[2,2-dimethyl-pent-4-en-(E)-ylidene]-amine
  参考文献：
  名称：

  Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allyl enamines

  摘要：

  The 3-aza-Cope rearrangement of the N-alkyl-N-allylenamines derived from isobutyraldehyde, which proceeds thermally at 250-degrees-C, has been accelerated by a variety of electrophilic reagents to give gamma,delta-unsaturated imines. Protic acids, such as HCl (0.5 equiv), and the Lewis acidic reagents TiCl4 (0.1-0.2 equiv), Et2O.BF3 (0.5 equiv), and AlMe3 (1.0 equiv) produced complete [3,3] rearrangement of substrates at 111-degrees-C. By increasing the Lewis acidity of the aluminum reagents, this transformation was achieved at 50-degrees-C with ClAlMe2, Cl2AlMe, and methylaluminum bis(2,6-diphenylphenoxide). Reaction conditions were studied initially by GLC analysis of the N-isobutyl derivative. These optimum conditions were then used to obtain isolated yields of 59-99% for rearrangement and in situ LiAlH4 reduction of the analogous N-methylcyclohexyl substrate to the corresponding delta,epsilon-unsaturated amine. Substrates derived from 2-phenylpropanal, n-butanal, cyclohexanone, and cyclopentanone were used to examine the general effectiveness of HCl, TiCl4, and AlMe3 as reagents for acceleration of the [3,3] rearrangement. The most versatile and efficient reagent for promoting this reaction, AlMe3, produced overall yields of 83-96% for the two-step rearrangement and reduction of these substrates.

  DOI：

  10.1021/jo00028a016
• 作为产物：
  描述：

  N-(2-methylpropylidene)-2-propenyl-1-amine 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.5h， 生成 N-(2-Methyl-1-propen-1-yl)-N-2-propen-1-ylcyclohexanemethanamine
  参考文献：
  名称：

  Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allyl enamines

  摘要：

  The 3-aza-Cope rearrangement of the N-alkyl-N-allylenamines derived from isobutyraldehyde, which proceeds thermally at 250-degrees-C, has been accelerated by a variety of electrophilic reagents to give gamma,delta-unsaturated imines. Protic acids, such as HCl (0.5 equiv), and the Lewis acidic reagents TiCl4 (0.1-0.2 equiv), Et2O.BF3 (0.5 equiv), and AlMe3 (1.0 equiv) produced complete [3,3] rearrangement of substrates at 111-degrees-C. By increasing the Lewis acidity of the aluminum reagents, this transformation was achieved at 50-degrees-C with ClAlMe2, Cl2AlMe, and methylaluminum bis(2,6-diphenylphenoxide). Reaction conditions were studied initially by GLC analysis of the N-isobutyl derivative. These optimum conditions were then used to obtain isolated yields of 59-99% for rearrangement and in situ LiAlH4 reduction of the analogous N-methylcyclohexyl substrate to the corresponding delta,epsilon-unsaturated amine. Substrates derived from 2-phenylpropanal, n-butanal, cyclohexanone, and cyclopentanone were used to examine the general effectiveness of HCl, TiCl4, and AlMe3 as reagents for acceleration of the [3,3] rearrangement. The most versatile and efficient reagent for promoting this reaction, AlMe3, produced overall yields of 83-96% for the two-step rearrangement and reduction of these substrates.

  DOI：

  10.1021/jo00028a016