(E)-N,N-dibenzyl-3-(2-methylphenyl)-2-propenylamine

• 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-(2-methylphenyl)-2-propenylamine
• 英文别名: (E)-N,N-dibenzyl-3-(o-tolyl)prop-2-en-1-amine；(E)-N,N-dibenzyl-3-(2-methylphenyl)prop-2-en-1-amine
• 化学式: C₂₄H₂₅N
• 分子量: 327.469
• InChiKey: VGQCAUYUNAGEII-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (E)-3-(2-methylphenyl)-2-propenol 在 亚磷酸三苯酯 、 4-二甲氨基吡啶 、 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.17h， 生成 (E)-N,N-dibenzyl-3-(2-methylphenyl)-2-propenylamine
  参考文献：
  名称：

  低催化剂负载量的 Pd(OAc)2/P(OPh)3 体系催化的好氧烯丙基胺化

  摘要：

  Pd(OAc) 2 /P(OPh) 3组合在有氧条件下催化辻-特罗斯特型烯丙基胺化。仅当使用烯丙基磷酸盐作为亲电子试剂时，芳族和脂肪族仲胺都可通过少量催化剂体系（通常为 0.02 mol% Pd）转化为相应的烯丙基胺。其他典型的亲电子试剂，例如乙酸烯丙酯和碳酸酯，具有轻微的反应性。机械实验表明，原位形成的 Pd(0) 配合物 Pd[P(OPh) 3 ] 3是一种活性物质。

  DOI：

  10.1021/acs.joc.1c02768

文献信息

• β-Regioselective intermolecular Heck arylation of N,N-disubstituted allylamines
  作者：J Wu、J.-F Marcoux、I.W Davies、P.J Reider

  DOI：10.1016/s0040-4039(00)01914-6

  日期：2001.1

  β-Regioselectivity has been demonstrated for the Heck arylation of N,N-disubstituted allylamines. The scope and limitations of the reaction were demonstrated by the coupling of N,N-dibenzylallylamine with a variety of substituted aryl triflates. This methodology represents a straightforward approach for the efficient preparation of a variety of primary β-aryl allyl amines.

  已经证明了N，N-二取代的烯丙基胺的Heck芳基化的β-区域选择性。通过N，N-二苄基烯丙基胺与各种取代的芳基三氟甲磺酸酯的偶合证明了反应的范围和局限性。该方法学代表了一种有效制备各种伯β-芳基烯丙基胺的直接方法。
• 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。
• 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.
• Aerobic Allylic Amination Catalyzed by a Pd(OAc)₂/P(OPh)₃ System with Low Catalyst Loading
  作者：Taiga Yurino、Sunaho Saito、Mizuki Ichihashi、Takeshi Ohkuma

  DOI：10.1021/acs.joc.1c02768

  日期：2022.3.4

  A Pd(OAc)2/P(OPh)3 combination catalyzed Tsuji–Trost-type allylic amination under aerobic conditions. Both aromatic and aliphatic secondary amines were transformed into the corresponding allylic amines with a tiny amount of the catalyst system (typically 0.02 mol % Pd), only when allylic phosphates were employed as electrophiles. Other typical electrophiles, such as allylic acetate and carbonate, were

  Pd(OAc) 2 /P(OPh) 3组合在有氧条件下催化辻-特罗斯特型烯丙基胺化。仅当使用烯丙基磷酸盐作为亲电子试剂时，芳族和脂肪族仲胺都可通过少量催化剂体系（通常为 0.02 mol% Pd）转化为相应的烯丙基胺。其他典型的亲电子试剂，例如乙酸烯丙酯和碳酸酯，具有轻微的反应性。机械实验表明，原位形成的 Pd(0) 配合物 Pd[P(OPh) 3 ] 3是一种活性物质。