(E)-3-ethylidene-1-tert-butylpiperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-3-ethylidene-1-tert-butylpiperidine
• 英文别名: (3E)-1-tert-butyl-3-ethylidenepiperidine
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: BDAXCPHGWMMWBQ-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  3-(3-chloropropyl)-2-(N-tert-butylamino)-4-pentenenitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (E)-3-ethylidene-1-tert-butylpiperidine
  参考文献：
  名称：

  Synthesis of 3-vinylpiperidines, 3-ethylidenepiperidines and 5-functionalized-1,2,3,4-tetrahydropyridines

  摘要：

  Reaction of 1-azapentadienyl anions, generated by deprotonation of N-(2-buten-1-ylidene)alkylamines, with 1-bromo-3-chloropropane led to the formation of N-[2-(3-chloropropyl)-3-buten-1-ylidene]alkylamines. By reaction with nucleophiles and bases, the latter functionalized imines were converted into unsaturated piperidines, i.e. 3-vinylpiperidines, 3-ethylidenepiperidines, 5-vinyl-1,2,3,4-tetrahydropyridines and 5-(2-cyanoethyl)-1,2,3,4-tetrahydropyridines. 5-Vinyl-1,2,3,4-tetrahydropyridines proved to be suitable dienes in Diels-Alder reactions with N-phenylmaleimide, giving rise to octahydro-1H-pyrrolo[3,4h]quinoline-1,3-diones. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00019-2

文献信息

• <i>N</i>-Heterocycles from Chromium Aminocarbenes
  作者：Martin Déry、Kevin Assouvie、Nora Heinrich、Isabelle Rajotte、Louis-Philippe D. Lefebvre、Marc-André Legault、Claude Spino

  DOI：10.1021/acs.orglett.5b00313

  日期：2015.3.6

  The initial [2 + 2]-cycloadduct between a chromium aminocarbene and a tethered alkene undergoes a beta-hydrogen elimination very efficiently when triphenylphosphine is added as a ligand. The reaction gives cyclic enamines or homoenamines depending on the substitution on the alkene.
• Synthesis of 3-vinylpiperidines, 3-ethylidenepiperidines and 5-functionalized-1,2,3,4-tetrahydropyridines
  作者：Wim Aelterman、Norbert De Kimpe

  DOI：10.1016/s0040-4020(98)00019-2

  日期：1998.3

  Reaction of 1-azapentadienyl anions, generated by deprotonation of N-(2-buten-1-ylidene)alkylamines, with 1-bromo-3-chloropropane led to the formation of N-[2-(3-chloropropyl)-3-buten-1-ylidene]alkylamines. By reaction with nucleophiles and bases, the latter functionalized imines were converted into unsaturated piperidines, i.e. 3-vinylpiperidines, 3-ethylidenepiperidines, 5-vinyl-1,2,3,4-tetrahydropyridines and 5-(2-cyanoethyl)-1,2,3,4-tetrahydropyridines. 5-Vinyl-1,2,3,4-tetrahydropyridines proved to be suitable dienes in Diels-Alder reactions with N-phenylmaleimide, giving rise to octahydro-1H-pyrrolo[3,4h]quinoline-1,3-diones. (C) 1998 Elsevier Science Ltd. All rights reserved.