(E)-N-benzyl-N-cinnamylbenzamide | 40032-56-2

• 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)-N-benzyl-N-cinnamylbenzamide
• 英文别名: N-benzyl-N-cinnamylbenzamide；Benzamide, N-(phenylmethyl)-N-(3-phenyl-2-propenyl)-, (E)-；N-benzyl-N-[(E)-3-phenylprop-2-enyl]benzamide
• CAS: 40032-56-2
• 化学式: C₂₃H₂₁NO
• 分子量: 327.426
• InChiKey: XDRQUZIQMQFZLX-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式-BETA-苯乙烯硼酸 在 magnesium sulfate 、 lithium tert-butoxide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (E)-N-benzyl-N-cinnamylbenzamide
  参考文献：
  名称：

  10.1002/anie.202409310

  摘要：

  Allylic amines are prevalent and vital structural components present in many bioactive compounds and natural products. Additionally, they serve as valuable intermediates and building blocks, with wide‐ranging applications in organic synthesis. However, direct α‐C(sp3)‐H alkenylation of feedstock amines, particularly for the preparation of α‐alkenylated cyclic amines, has posed a longstanding challenge. Herein, we present a general, mild, operationally simple, and transition‐metal‐free α‐alkenylation of various readily available amines with alkenylborate esters in excellent E/Z ‐ and diastereoselectivities. This method features good compatibility with water and oxygen, broad substrate scope, and excellent functional group tolerance, thereby enabling the late‐stage modification of various complex molecules. Mechanistic studies suggest that the formation of a photoactive electron donor‐acceptor complex between 2‐iodobenzamide and the tetraalkoxyborate anion, which subsequently undergoes photoinduced single electron transfer and intramolecular 1,5‐hydrogen atom transfer to generate the crucial α‐amino radicals, is the key to success of this chemistry.

  DOI：

  10.1002/anie.202409310

文献信息

• One-Pot Synthesis of Allylamine Derivatives by Iodine- Catalyzed Three-Component Reaction of N-Heterocycles, Paraformaldehyde and Styrenes
  作者：Zheng-Jun Quan、Wang-Hua Hu、Zhang Zhang、Yu-Xia Da、Xiao-Dong Jia、Xi-Cun Wang

  DOI：10.1002/adsc.201201097

  日期：2013.3.25

  The molecular iodine‐catalyzed three‐component reaction of amides or amide derivatives, paraformaldehyde and styrenes allows for the clean generation of allylamine derivatives in good yields and high regioselectivities. The reaction, forming water as the sole co‐product, is an experimentally easy to conduct transformation in the absence of transition metals under mild conditions.

  酰胺或酰胺衍生物，多聚甲醛和苯乙烯的分子碘催化三组分反应可实现高收率和高区域选择性的烯丙基胺衍生物的清洁生成。该反应形成水是唯一的副产物，在温和条件下，在没有过渡金属的情况下，该实验很容易进行转化。