3-氨基-3-(4-甲基苯基)丙-2-烯腈 | 17196-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-3-(4-甲基苯基)丙-2-烯腈
• 英文名称: 3-amino-3-p-tolylacrylonitrile
• 英文别名: β-amino-4-methyl-cinnamonitrile；β-Amino-4-methyl-zimtsaeure-nitril；β-Amino-4-methyl-cinnamonitril；β-Amino-β-p-tolyl-acrylsaeurenitril；p-Toluacetodinitril；β-Imino-β-p-tolyl-propionsaeure-nitril；3-Amino-3-(4-methylphenyl)prop-2-enenitrile
• CAS: 17196-75-7；60375-52-2；25354-55-6
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: AVWQBZGANBIJBI-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±21.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氨基-3-(4-甲基苯基)丙-2-烯腈 在 盐酸 、 sodium cyanoborohydride 、 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以53%的产率得到3-amino-3-p-tolylpropanenitrile
  参考文献：
  名称：

  Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

  摘要：

  A range of beta-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the corresponding amides using the nitrile biocatalytic activity of Rhodococccus rhodochrous ATCC BAA-870. Results showed that the nitrile hydratase enzyme was enantioselective for these compounds, in particular 3-amino-3-p-tolylpropanenitrile and 3-amino-3-(4-methoxyphenyl)propanenitrile and the corresponding amides (up to 85% in one case). The reactions were performed at pH 9.0 after initial attempts at pH 7.0 were unsuccessful, most likely as a result of protonation of the 3-amino group at the lower pH. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.12.005
• 作为产物：
  描述：

  对甲苯腈 、 乙腈 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 3-氨基-3-(4-甲基苯基)丙-2-烯腈
  参考文献：
  名称：

  β-氨基丙烯腈的高效RhI催化不对称加氢

  摘要：

  TangPhos需要花费两个时间：β-氨基丙烯腈可以很容易地由乙腈制备。通过使用Rh-TangPhos（TangPhos = 1,1'-二叔丁基-（2,2'）-diphospholane）催化剂体系，两种E / Z异构体均以优异的对映选择性进行氢化。手性β-氨基腈是许多药物的重要手性基石。

  DOI：

  10.1002/chem.201000325

文献信息

• Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl <i>N</i>²-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis
  作者：Hao-Nan Liu、Hao-Qiang Cao、Chi Wai Cheung、Jun-An Ma

  DOI：10.1021/acs.orglett.0c00006

  日期：2020.2.21

  Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl

  N-芳基1,2,3-三唑-羧酸烷基酯是药物化学中的重要分子或中间体，但N2-芳基对应物的合成仍然难以捉摸。在本文中，我们描述了3-氨基丙烯酸烷基酯与芳基重氮盐的Cu介导的环化反应，这两种都是容易获得的底物。此外，2-氨基丙烯酸烷基酯也是可行的底物。N 2-芳基1,2,3-三唑-羧酸烷基酯及其类似物可以在温和的条件下快速制备。特别地，该方案允许人们访问碳酸酐酶抑制剂和塞来昔布的几种药物样变体。
• .beta.-Aminocinnamonitriles as potential antiinflammatory agents
  作者：S. A. Lang、E. Cohen

  DOI：10.1021/jm00238a027

  日期：1975.4

  A number of beta-aminocinnamonitriles have been prepared by the reaction of salts of acetonitrile and propionitrile with benzonitrile. These materials were evaluated in the carrageenan antiinflammatory screen in Royal Hart, Wistar strain rats. Despite good weight gains in the parent molecule, beta-aminocinnamonitrile (1), only marginal activity was found in related compounds and some possible "metabolites

  通过乙腈和丙腈的盐与苄腈的反应已经制备了许多β-氨基肉桂腈。这些材料在Wistar品系Royal Hart大鼠的角叉菜胶消炎筛选中进行了评估。尽管母体分子β-氨基肉桂腈（1）的体重增加了很多，但在相关化合物和某些可能的“代谢产物”中仅发现了少量活性。
• Annulation of β-Enaminonitriles with Alkynes via Rh^III-Catalyzed C–H Activation: Direct Access to Highly Substituted 1-Naphthylamines and Naphtho[1,8-<i>bc</i>]pyridines
  作者：Haili Wang、Hong Xu、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.8b02341

  日期：2018.9.21

  A Cp*RhIII-catalyzed oxidative annulation of β-enaminonitriles with alkynes was reported to achieve selective synthesis of polysubstituted 1-naphthylamines and naphtho[1,8-bc]pyridines via multiple C–H activations. Assisted by a naphthylamine NH2 group, 1-naphthylamines were also readily cyclized to produce naphtho[1,8-bc]pyridines. In addition, the obtained naphtho[1,8-bc]pyridine derivatives exhibit

  据报道，Cp * Rh III催化的炔烃对β-烯腈的氧化环化反应通过多种C-H活化选择性地合成了多取代的1-萘胺和萘[1,8- bc ]吡啶。在萘胺NH 2基团的辅助下，1-萘胺也很容易被环化以生成萘[1,8- bc ]吡啶。此外，所获得的萘并[1,8- bc ]吡啶衍生物在固态下表现出强烈的荧光。
• FeCl3-Promoted Facile Synthesis of Multiply Arylated Nicotinonitriles
  作者：Kento Iwai、Nagatoshi Nishiwaki、Haruka Yamauchi、Soichi Yokoyama

  DOI：10.1055/a-1731-9464

  日期：2022.5

  Many biologically active nicotinonitriles have been reported to date. Consequently, the development of synthetic methods for multiply arylated/alkylated nicotinonitriles remains a sought-after field of research. In the present work, a new synthetic strategy for multi-substituted nicotinonitriles is described. A FeCl3-promoted condensation–cyclization reaction of an enamino nitrile and α,β-unsaturated

  迄今为止，已经报道了许多具有生物活性的烟腈。因此，多芳基化/烷基化烟腈的合成方法的开发仍然是一个受欢迎的研究领域。在目前的工作中，描述了一种新的多取代烟腈合成策略。FeCl3 促进的烯胺腈和 α,β-不饱和酮的缩合-环化反应在多种底物下有效进行。值得注意的是，该方法仅通过三个步骤即可促进获得完全和不同取代的烟腈，包括四芳基化烟腈。利用氰基的官能团，实现了铜催化的烟腈环化反应，得到苯并[c][2,7]萘啶-5(6H)-酮。
• Trisubstituted thiazoles by a 6π-electrocyclization of iminothiocarbonyl ylides
  作者：A. Corsaro、M. Tarantello、G. Purrello

  DOI：10.1016/s0040-4039(01)81891-8

  日期：1981.1

  Iminothiocarbonyl ylides are generated by a sulfur ligand exchange reaction of sulfonium salts and undergo a 6π-electrocyclic closure and aromatization to trisubstituted thiazoles. Related carbonyl ylides preferred a 4π-electrocyclization.

  亚氨基硫代羰基烷基化物是由sulf盐的硫配体交换反应生成的，并经过6π-电环封闭并芳构化为三取代的噻唑。相关的羰基酰化物优选4π-电环化。