(E)-1-(4-phenylbut-3-en-2-yl)piperidine | 35066-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(4-phenylbut-3-en-2-yl)piperidine
• 英文别名: 1-(1-methyl-3t-phenyl-allyl)-piperidine；1-(1-Methyl-3t-phenyl-allyl)-piperidin
• CAS: 35066-84-3
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: BCJBZWSUQLURGI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-phenylbut-3-en-2-yl)piperidine 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 (Z)-1-(4-phenylbut-3-en-2-yl)piperidine
  参考文献：
  名称：

  Facile Synthesis of Z-Alkenes via Uphill Catalysis

  摘要：

  Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.

  DOI：

  10.1021/ja5019749
• 作为产物：
  描述：

  ethyl (E)-1-phenylbut-1-en-3-ol 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (E)-1-(4-phenylbut-3-en-2-yl)piperidine
  参考文献：
  名称：

  Facile Synthesis of Z-Alkenes via Uphill Catalysis

  摘要：

  Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.

  DOI：

  10.1021/ja5019749

文献信息

• Asymmetric Aza-Claisen Rearrangement between Enantioenriched α-Chiral Allylamines and Allenones
  作者：Rui-Han Dai、Qi Wang、Zhi-Xiong Chen、Shi-Kai Tian

  DOI：10.1021/acs.joc.0c02721

  日期：2021.2.5

  An unprecedented asymmetric aza-Claisen rearrangement between enantioenriched α-chiral allylamines and allenones was found to proceed in the absence of catalysts and additives at room temperature. The rearrangement, followed by hydrolysis, provides convenient access to structurally diverse δ-chiral β-diketones in good to excellent yields with excellent retention of enantiopurity. This protocol proved

  发现在室温下在不存在催化剂和添加剂的情况下，对映体富集的α-手性烯丙胺和烯丙酮之间空前的不对称氮杂-克莱森重排发生。重排，然后水解，可以方便地获得结构多样的δ-手性β-二酮，产率高至优异，对映体纯度保持优异。实践证明，该协议对构建具有高对映体纯度的全碳四元立体中心非常有效。
• Extension of the Leuckart Synthesis of Tertiary Amines, Including its Application to α,β-Unsaturated Carbonyl Compounds¹
  作者：J. F. Bunnett、Jean Lovendahl Marks、Henry Moe

  DOI：10.1021/ja01100a504

  日期：1953.2