N-<2-(2-methylbutyl)-4-methyl-1-hexylidene>-tert-butylamine | 144226-83-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-<2-(2-methylbutyl)-4-methyl-1-hexylidene>-tert-butylamine
• 英文别名: N-tert-butyl-4-methyl-2-(2-methylbutyl)hexan-1-imine
• CAS: 144226-83-5
• 化学式: C₁₆H₃₃N
• 分子量: 239.445
• InChiKey: URLGXIYQGXMEBU-UHFFFAOYSA-N

物化性质

• 沸点：
  310.7±15.0 °C(Predicted)
• 密度：
  0.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-叔丁基乙基亚胺 、 1-溴-2-甲基丁烷 在 lithium diisopropyl amide 作用下， 生成 N-(4-methyl-1-hexylidene)-tert-butylamine 、 N-<2-(2-methylbutyl)-4-methyl-1-hexylidene>-tert-butylamine
  参考文献：
  名称：

  Synthesis of stenusine, the spreading agent of the beetle Stenus comma

  摘要：

  Stenusine [1-ethyl-3-(2-methylbutyl)piperidine], the spreading agent of Stenus comma, was synthesized by a six-step sequence in 21 % overall yield from acetaldehyde. Acetaldehyde was converted into the corresponding N-tert-butyl aldimine, which was sequentially alkylated via its 1-azaallylic anion with 1-bromo-2-methylbutane and 1-bromo-3-chloropropane. The resulting delta-chloro aldimine was hydrolyzed into the delta-chloro aldehyde, which was converted into the corresponding N-ethyl aldimine. The latter labile delta-chloro aldimine was cyclized with lithium aluminum hydride to afford stenusine. The 1-tert-butyl analogue of stenusine was synthesized using an analogous route.

  DOI：

  10.1021/jo00053a025

文献信息

• Synthesis of stenusine, the spreading agent of the beetle Stenus comma
  作者：Christian Stevens、Norbert De Kimpe

  DOI：10.1021/jo00053a025

  日期：1993.1

  Stenusine [1-ethyl-3-(2-methylbutyl)piperidine], the spreading agent of Stenus comma, was synthesized by a six-step sequence in 21 % overall yield from acetaldehyde. Acetaldehyde was converted into the corresponding N-tert-butyl aldimine, which was sequentially alkylated via its 1-azaallylic anion with 1-bromo-2-methylbutane and 1-bromo-3-chloropropane. The resulting delta-chloro aldimine was hydrolyzed into the delta-chloro aldehyde, which was converted into the corresponding N-ethyl aldimine. The latter labile delta-chloro aldimine was cyclized with lithium aluminum hydride to afford stenusine. The 1-tert-butyl analogue of stenusine was synthesized using an analogous route.