1-乙基-3-(2-甲基丁基)哌啶 | 54985-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-乙基-3-(2-甲基丁基)哌啶
• 英文名称: stenusine
• 英文别名: 1-Ethyl-3-(2-methylbutyl)piperidine
• CAS: 54985-88-5
• 化学式: C₁₂H₂₅N
• 分子量: 183.337
• InChiKey: DYZADDXQHPDPNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(4-methyl-1-hexylidene)-tert-butylamine 在 lithium aluminium tetrahydride 、 草酸 、 magnesium sulfate 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 1-乙基-3-(2-甲基丁基)哌啶
  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.