N-benzyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline

• 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: N-benzyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline
• 英文别名: N-benzyl-N-[(E)-3-phenyl-2-propenyl]aniline；N-Benzyl-N-cinnamylphenylamine；N-benzyl-N-cinnamylaniline；N-benzyl-N-[(E)-3-phenylprop-2-enyl]aniline
• 化学式: C₂₂H₂₁N
• 分子量: 299.415
• InChiKey: PTRLRJBLPVQTSS-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 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：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline 在 polyphosphoric acid 作用下， 以85%的产率得到1-benzyl-4-phenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  四氢喹啉衍生物的简便合成及Aza-Cope重排研究

  摘要：

  摘要 已经报道了通过多磷酸辅助由苯胺制备的 N-芳基烯丙基苯胺的反应合成 1,2,3,4-四氢喹啉衍生物的一种简单而新颖的方法。该方法的通用性和范围已通过将其扩展到 1,2,5,6-四氢-4H-吡咯并[3,2,1-ij] 喹啉（lilolidine）和 2,3,6， 7-四氢-1H,5H-吡啶并[3,2,1-ij]喹啉（julolide）。此外，已经证明了路易斯酸介导的各种 N-芳基烯丙基苯胺的氮杂-科普重排。

  DOI：

  10.1080/00397911.2010.493258
• 作为产物：
  描述：

  1-苯基-1-丙炔 、 苯甲基苯胺 在 四(三苯基膦)钯 、 苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以94%的产率得到N-benzyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline
  参考文献：
  名称：

  A Convenient and Efficient Route for the Allylation of Aromatic Amines and α-Aryl Aldehydes with Alkynes in the Presence of a Pd(0)/PhCOOH Combined Catalyst System

  摘要：

  The allylation of aromatic amines with alkynes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)(4) and benzoic acid. The allylation products were obtained in high yields in a regio- and stereoselective manner. The effect of various groups on the nitrogen atom of anilines was studied. Regardless of the substituent (electron withdrawing or electron donating) on the aromatic ring, the reaction proceeded well. Various functionalities, including -CH3, -OMe, -Cl, -CN, -COOMe, -NO2 and -COCH3 were tolerated under the reaction conditions. Similarly, the allylation of alpha-aryl aldehydes proceeded well with the same level of regio- and stereoselectivity as the allylation of aromatic amines. This reaction provides the second example of the transition metal catalyzed direct alpha-allylation of aldehydes.

  DOI：

  10.1021/jo0485684

文献信息

• Allylic Amination via Decarboxylative C-N Bond Formation
  作者：Jon A. Tunge、Shelli R. Mellegaard-Waetzig、Dinesh Kumar Rayabarapu

  DOI：10.1055/s-2005-918949

  日期：——

  This manuscript details the development of a palladium-catalyzed allylic amination that proceeds via decarboxylation of ­allylic carbamates. Both saturated and aromatic heterocycles undergo decarboxylative rearrangement in good yields. The mechanism of allylation of heteroaromatic amines involves the formation of π-allyl palladium complexes followed by decarboxylation of the ­carbamate. Finally, the heteroaromatic anion equivalent is allylated to provide allylic amines.

  这篇手稿详细描述了一种通过去羧化烯丙基碳酸酯进行的钯催化烯丙基胺化反应。饱和和芳香杂环在良好产率下经历去羧 rearrangement。杂芳香胺的烯丙基化机理涉及 π-烯丙基钯络合物的形成，随后是碳酸酯的去羧化。最后，杂芳香阴离子等价物被烯丙基化，生成烯丙基胺。
• 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。
• Highly Coordinated Tin Hydrides: A Novel Synthesis of Tertiary Amines via Hydrostannation of Imines
  作者：Takayo Kawakami、Takayuki Sugimoto、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1021/jo00114a014

  日期：1995.5

  The highly coordinated tin hydride, Bu(2)SnClH-HMPA (B), is shown to be an effective agent for the reduction of imines. The subsequent alkylation of the resulting intermediate tin amides permitted the preparation of a series of tertiary amines in a one-pot procedure. The spectral identification of the novel tin hydrides, B and Bu(2)SnClH-Bu(4)NF, was accomplished by H-1, C-13, and Sn-119 NMR and FT-IR studies.