2-nitro-N-[(2E)-3-phenylprop-2-en-1-yl]aniline | 213326-06-8

• 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: 2-nitro-N-[(2E)-3-phenylprop-2-en-1-yl]aniline
• 英文别名: N-cinnamyl-2-nitroaniline；2-nitro-N-[(E)-3-phenylprop-2-enyl]aniline
• CAS: 213326-06-8
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: XZBJEHWRSDYFKT-RMKNXTFCSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  454.2±38.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitro-N-[(2E)-3-phenylprop-2-en-1-yl]aniline 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 一氧化碳 、 邻菲罗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、607.99 kPa 条件下， 反应 92.75h， 以54%的产率得到(E)-2-styryl-1H-benzo[d]imidazole
  参考文献：
  名称：

  钯催化N-烯丙基-或N-苄基-2-硝基苯甲胺的N杂环化：2-取代的苯并咪唑的合成

  摘要：

  已经开发了使用一氧化碳作为最终还原剂的钯催化的N-烯丙基-或N-苄基-2-硝基苯甲胺的还原性N-杂环环合，得到2-取代的苯并咪唑。

  DOI：

  10.1016/j.tet.2007.05.010
• 作为产物：
  描述：

  1-苯基-1-丙炔 、 2-硝基苯胺 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 8.0h， 以92%的产率得到2-nitro-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

• Simple and Convenient Approach for Synthesis of Tetrahydroquinoline Derivatives and Studies on Aza-Cope Rearrangement
  作者：V. S. Prasada Rao Lingam、Abraham Thomas、Khagga Mukkanti、Balasubramanian Gopalan

  DOI：10.1080/00397911.2010.493258

  日期：2011.5.4

  Abstract A simple and novel synthesis of 1,2,3,4-tetrahydroquinoline derivatives by polyphosphoric acid–assisted reaction of N-aryl allyl anilines prepared from anilines has been reported. The generality and scope of the approach has been demonstrated by extending it to the synthesis of 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline (lilolidine) and 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline

  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。
• Palladium(0)-Catalyzed Allylation of Highly Acidic and Nonnucleophilic Anilines. The Origin of Stereochemical Scrambling When Using Allylic Carbonates
  作者：Marcial Moreno-Mañas、Lurdes Morral、Roser Pleixats

  DOI：10.1021/jo980209j

  日期：1998.9.1

  nitroanilines are efficiently allylated under palladium catalysis using allyl carbonates as allylating reagents. A stereochemical study of the reactions of ethyl cis-5-methyl-2-cyclohexenylcarbonate with 4-nitro- and 2,4-dinitroaniline was performed. Bidentate phosphines as stabilizing ligands gave clean retention of configuration whereas triphenylphosphine permitted cis-trans isomerization of the allylic carbonate

  酸性苯胺（如二苯胺，吩噻嗪和硝基苯胺）在钯催化下使用碳酸烯丙酯作为烯丙基化试剂可以有效地烯丙基化。进行了立体化学研究顺式5-甲基-2-环己烯基碳酸乙酯与4-硝基和2,4-二硝基苯胺的反应。二齿膦作为稳定的配体，使构型保持清晰，而三苯膦则允许烯丙基碳酸酯的顺反异构化，烯丙基化反应发生在Curtin-Hammet预平衡条件下。
• Palladium-Catalyzed Allylation of Acidic and Less Nucleophilic Anilines Using Allylic Alcohols Directly
  作者：Yi-Chun Hsu、Kim-Hong Gan、Shyh-Chyun Yang

  DOI：10.1248/cpb.53.1266

  日期：——

  activation of C-O bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium(IV) isoproxide and 4 A molecular sieves. The acidic and less nucleophilic anilines such as diphenylamine, phenothiazine, 4-cyanoaniline, and nitroanilines are efficiently allylated under palladium catalysis using allylic alcohols as allylating reagents.

  通过在异丙氧基钛（IV）和4 A分子筛的存在下进行反应，可以加快钯络合物在烯丙醇中CO键的直接活化。酸性和较少亲核性的苯胺，如二苯胺，吩噻嗪，4-氰基苯胺和硝基苯胺，在钯催化下使用烯丙醇作为烯丙基化试剂可以有效地烯丙基化。
• 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.
• 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.