N-cinnamyl-2-cyanobenzenamine

• 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-cinnamyl-2-cyanobenzenamine
• 英文别名: N-cinnamyl-2-cyanoaniline；2-[[(E)-3-phenylprop-2-enyl]amino]benzonitrile
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: DTXNNJVQVLXNRG-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基-1-丙炔 、 2-氨基苯甲腈 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 苯甲酸 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 甲苯 为溶剂， 以88%的产率得到N-cinnamyl-2-cyanobenzenamine
  参考文献：
  名称：

  在 50 °C 下钯催化亲核试剂与炔烃的烯丙基化 - 2-（二环己基膦酰基）-2'-（二甲氨基）联苯作为配体的显着效果

  摘要：

  在催化量的 Pd2(dba)3·CHCl3 (5 mol-%) 和 2-(二环己基膦酰基)-2'-(二甲氨基)联苯 (I; 20 mol-%) 在甲苯中，而当使用 Pd(PPh3)4 或 Pd2(dba)3·CHCl3/PPh3 时，反应需要 100 °C 才能完成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600337

文献信息

• Deammoniative Condensation of Primary Allylic Amines with Nonallylic Amines
  作者：Yong Wang、Manbo Li、Xiantao Ma、Congrong Liu、Yonghong Gu、Shi-Kai Tian

  DOI：10.1002/cjoc.201400406

  日期：2014.8

  through CN bond cleavage. In the presence of 5 mol% palladium diacetate, 10 mol% 1,4‐bis(diphenylphosphino)butane (dppb), and 5 mol% p‐toluenesulfonic acid (TsOH), a range of α‐unbranched primary allylic amines smoothly underwent deammoniative condensation with nonallylic amines in an α‐selective fashion to give structurally diverse secondary and tertiary amines in good to excellent yields and E selectivity

  与nonallylic胺伯烯丙基胺类空前deammoniative缩合反应已经通过C语言开发 N键裂解。在存在5 mol％的二乙酸钯，10 mol％的1,4-双（二苯基膦基）丁烷（dppb）和5 mol％的对甲苯磺酸（TsOH）的情况下，一系列α支链的伯烯丙基胺顺利进行了脱氨反应与非烯丙基胺以α选择性方式缩合，得到结构多样的仲胺和叔胺，并具有优异的产率和E选择性。用外消旋的2,2'-双（二苯基膦基）-1,1'-联萘（BINAP）代替dppb可以使对映体富集的α脱氨缩合手性伯烯丙基胺与非烯丙基胺，以完全保留构型。反应混合物的电喷雾电离（ESI）质谱分析可以鉴定一些π-烯丙基钯中间体，并且提出了可能的机理来解释脱氨缩合反应的区域选择性和立体选择性。
• The Synthesis and Application of 2-Cyano and -Ester Containing Anilines: Selective Copper-Catalyzed Reductive Amination, N-Benz­ylation, and Cyclization Reactions
  作者：Feng Xie、Bin Li、Ziwei Huang、Zirui Lin、Jiexiong Mai、Shaohuan Lv、Youxue Yuan、Wenbing Zhang、Fan Qian

  DOI：10.1055/a-1840-5768

  日期：2022.10

  2-ester anilines is described via efficient and selective copper(II)-catalyzed reductive amination via hydrosilylation process. Both 2-cyano and 2-ester anilines were successfully synthesized with good functional group tolerance and high selectivity. The application of the 2-cyano and -iodine containing anilines was developed in the synthesis of indoloindole derivatives via CuSO4-catalyzed N-benzylation

  通过高效和选择性的铜 (II) 催化还原胺化，通过氢化硅烷化过程描述了一种方便实用的 2-氰基和 2-酯苯胺途径。成功合成了具有良好官能团耐受性和高选择性的2-氰基苯胺和2-酯苯胺。通过CuSO 4催化的N-苄基化和“一锅”环化反应，开发了含2-氰基和-碘苯胺在吲哚吲哚衍生物的合成中的应用。更有趣的是，这些含 2-氰基和 2-酯的苯胺的光物理性质研究显示出优异的荧光性质，在不久的将来在开发有趣的近紫外光学器件方面具有巨大的应用潜力。
• 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
  作者：Nitin T. Patil、Huanyou Wu、Isao Kadota、Yoshinori Yamamoto

  DOI：10.1021/jo0485684

  日期：2004.12.1

  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.
• Direct palladium/carboxylic acid-catalyzed allylation of anilines with allylic alcohols in water
  作者：Shyh-Chyun Yang、Yi-Chun Hsu、Kim-Hong Gan

  DOI：10.1016/j.tet.2006.02.035

  日期：2006.4

  The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of anilines using allylic alcohols directly gave allylic anilines in good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Allylation of Pronucleophiles with Alkynes at 50 °C – Remarkable Effect of 2-(Dicyclohexylphosphanyl)-2′-(dimethylamino)biphenyl as Ligand
  作者：Nitin T. Patil、Dschun Song、Yoshinori Yamamoto

  DOI：10.1002/ejoc.200600337

  日期：2006.9

  The allylation of various pronucleophiles 1a–i with 1-phenylprop-1-yne (2) proceeded very smoothly at 50 °C in the presence of catalytic amounts of Pd2(dba)3·CHCl3 (5 mol-%) and 2-(dicyclohexylphosphanyl)-2′-(dimethylamino)biphenyl (I; 20 mol-%) in toluene, whilst when Pd(PPh3)4 or Pd2(dba)3·CHCl3/PPh3 were used, the reaction needed 100 °C for completion.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  在催化量的 Pd2(dba)3·CHCl3 (5 mol-%) 和 2-(二环己基膦酰基)-2'-(二甲氨基)联苯 (I; 20 mol-%) 在甲苯中，而当使用 Pd(PPh3)4 或 Pd2(dba)3·CHCl3/PPh3 时，反应需要 100 °C 才能完成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)