(E)-N,N-dibenzyl-3-(4-chlorophenyl)prop-2-en-1-amine | 1152652-47-5

• 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,N-dibenzyl-3-(4-chlorophenyl)prop-2-en-1-amine
• 英文别名: (E)-N,N-dibenzyl-3-(4-chlorophenyl)-2-propenylamine；(E)-dibenzyl-[3-(4-chlorophenyl)allyl]amine
• CAS: 1152652-47-5
• 化学式: C₂₃H₂₂ClN
• 分子量: 347.887
• InChiKey: YSAZGQRDQDZFAW-KPKJPENVSA-N

物化性质

• 沸点：
  473.8±33.0 °C(predicted)
• 密度：
  1.144±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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-(4-chlorophenyl)-2-propene-1-ol 、 二苄胺 在 2-(9-borabicyclo[3.3.1]nonanyl)ethyl(diphenyl)phosphine 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以88%的产率得到(E)-N,N-dibenzyl-3-(4-chlorophenyl)prop-2-en-1-amine
  参考文献：
  名称：

  含膦-硼烷配体的钯配合物催化的烯丙醇直接烯丙基胺化

  摘要：

  已经开发了通过使用钯催化剂和有机金属试剂例如有机硼烷和有机锌的烯丙基醇的直接亲电子，亲核和两亲烯丙基化。膦-硼烷化合物可作为钯催化的烯丙基醇直接烯丙基胺化的有效配体。因此，使用仲胺，即使在室温下，反应也仅需1小时即可完成。

  DOI：

  10.1021/acs.orglett.7b03023

文献信息

• Palladium-Catalyzed Vinylation of Aminals with Simple Alkenes: A New Strategy To Construct Allylamines
  作者：Yinjun Xie、Jianhua Hu、Yanyu Wang、Chungu Xia、Hanmin Huang

  DOI：10.1021/ja310848x

  日期：2012.12.26

  A novel, highly selective palladium-catalyzed vinylation reaction for the direct synthesis of allylic amines from styrenes and aminals has been established. The utility of this method was also demonstrated by the rapid synthesis of cinnarizine from aldehydes, amines, and simple alkenes in one-pot manner. Mechanistic studies suggested that the reaction proceeds through a valuable cyclometalated Pd(II) complex generated by the oxidative addition of aminal to a Pd(0) species.
• Palladium Nanoparticle-Catalyzed C−N Bond Formation. A Highly Regio- and Stereoselective Allylic Amination by Allyl Acetates
  作者：Laksmikanta Adak、Kalicharan Chattopadhyay、Brindaban C. Ranu

  DOI：10.1021/jo9003037

  日期：2009.5.15

  Palladium nanoparticles, generated in situ from the reaction of palladium(II) chloride, have been demonstrated to be an efficient catalyst for C-N bond formation. A variety of aliphatic and aromatic amines have been allylated by substituted and unsubstituted allyl acetates in high yields by using palladium nanoparticles in the presence of a base without any ligand. The allylations are highly regio- and stereoselective.
• Direct Allylic Amination of Allylic Alcohol Catalyzed by Palladium Complex Bearing Phosphine–Borane Ligand
  作者：Goki Hirata、Hideaki Satomura、Hidenobu Kumagae、Aika Shimizu、Gen Onodera、Masanari Kimura

  DOI：10.1021/acs.orglett.7b03023

  日期：2017.11.17

  The direct electrophilic, nucleophilic, and amphiphilic allylations of allylic alcohol by use of a palladium catalyst and organometallic reagents such as organoborane and organozinc has been developed. The phosphine–borane compound works as the effective ligand for palladium-catalyzed direct allylic amination of allylic alcohol. Thus, with secondary amines, the reaction was completed in only 1 h, even

  已经开发了通过使用钯催化剂和有机金属试剂例如有机硼烷和有机锌的烯丙基醇的直接亲电子，亲核和两亲烯丙基化。膦-硼烷化合物可作为钯催化的烯丙基醇直接烯丙基胺化的有效配体。因此，使用仲胺，即使在室温下，反应也仅需1小时即可完成。