(2S)-2-((E)-2-(4-acetylphenyl)vinyl)piperidine-1-carboxylic acid tert-butyl ester | 1565872-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-((E)-2-(4-acetylphenyl)vinyl)piperidine-1-carboxylic acid tert-butyl ester
• CAS: 1565872-72-1
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: GEWFFXIQOBIKGT-HGZMWJMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-((E)-2-(4-acetylphenyl)vinyl)piperidine-1-carboxylic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.08h， 以85%的产率得到(2S)-2-((E)-2-(4-acetylphenyl)vinyl)piperidine
  参考文献：
  名称：

  Pd- N -heterocyclic carbene catalyzed synthesis of piperidine alkene–alkaloids and their anti-cancer evaluation

  摘要：

  A facile synthesis of piperidine alkene-alkaloids including natural (+)-Caulophyllumine B in high yields has been developed by Heck cross-coupling reaction catalyzed by simple in situ formed palladium-N-heterocyclic carbenes (Pd-NHCs). Formation of Pd(0) nanoparticles has been noticed during the reaction course. The synthesized piperidine alkene-alkaloids were evaluated for in vitro anti-cancer activity against a panel of human tumor cell lines of lung, breast and ovarian. Several of these piperidine alkene-alkaloids were found to possess highest growth inhibition activity than the standard drug cisplatin and support the concept to modulate drug receptor interaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.108
• 作为产物：
  描述：

  1-Boc-哌啶 在 四丁基溴化铵 、 仲丁基锂 、 palladium diacetate 、 三乙胺 、 1,3-二-叔丁基咪唑氯化物 、 (+)-鹰爪豆碱 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 11.0h， 生成 (2S)-2-((E)-2-(4-acetylphenyl)vinyl)piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Pd- N -heterocyclic carbene catalyzed synthesis of piperidine alkene–alkaloids and their anti-cancer evaluation

  摘要：

  A facile synthesis of piperidine alkene-alkaloids including natural (+)-Caulophyllumine B in high yields has been developed by Heck cross-coupling reaction catalyzed by simple in situ formed palladium-N-heterocyclic carbenes (Pd-NHCs). Formation of Pd(0) nanoparticles has been noticed during the reaction course. The synthesized piperidine alkene-alkaloids were evaluated for in vitro anti-cancer activity against a panel of human tumor cell lines of lung, breast and ovarian. Several of these piperidine alkene-alkaloids were found to possess highest growth inhibition activity than the standard drug cisplatin and support the concept to modulate drug receptor interaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.108