4-methoxy-1-[4-methoxyanilino(phenylcarbonylimino)methylamino]benzene | 340034-03-9

• 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: 4-methoxy-1-[4-methoxyanilino(phenylcarbonylimino)methylamino]benzene
• 英文别名: N-[N,N'-bis(4-methoxyphenyl)carbamimidoyl]benzamide
• CAS: 340034-03-9
• 化学式: C₂₂H₂₁N₃O₃
• 分子量: 375.427
• InChiKey: NRGOFMPXPBZJCG-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C(Solv: ethanol (64-17-5))
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-1-[4-methoxyanilino(phenylcarbonylimino)methylamino]benzene 在 氢氧化钾 作用下， 生成 1,3-bis(4-methoxyphenyl)guanidine
  参考文献：
  名称：

  2,2,3-TRIMETHYLPENTANE.

  摘要：

  DOI：

  10.1021/ja02203a007
• 作为产物：
  描述：

  苯甲酰基异硫氰酸酯 在 四氯化碳 作用下， 生成 4-methoxy-1-[4-methoxyanilino(phenylcarbonylimino)methylamino]benzene
  参考文献：
  名称：

  2,2,3-TRIMETHYLPENTANE.

  摘要：

  DOI：

  10.1021/ja02203a007

文献信息

• Study of N -benzoyl-activation in the HgCl 2 -promoted guanylation reaction of thioureas. Synthesis and structural analysis of N -benzoyl-guanidines
  作者：Silvio Cunha、Maı́sa B Costa、Hamilton B Napolitano、Carlito Lariucci、Ivo Vencato

  DOI：10.1016/s0040-4020(00)01168-6

  日期：2001.2

  demonstrated that the benzoyl group is an activating group for thioureas in the HgCl2-guanylation reaction. Thus N-benzoyl-thioureas containing electronically neutral and even electron-withdrawing or electron-releasing substituents are converted into guanidines with reasonable yields. In addition, NMR and X-ray structural analyses were performed to understand the intra- and intermolecular features of the synthesized

  在这项工作中，证明了苯甲酰基是HgCl 2-鸟苷酸化反应中硫脲的活化基团。因此，含有电子中性且甚至吸电子或释放电子的取代基的N-苯甲酰基-硫脲以合理的产率转化为胍。此外，进行了NMR和X射线结构分析以了解合成胍的分子内和分子间特征。
• Bismuth nitrate pentahydrate: a new and environmentally benign reagent for guanidylation of N-benzoylthioureas
  作者：Silvio Cunha、Byanka R de Lima、Aparecido R de Souza

  DOI：10.1016/s0040-4039(01)02067-6

  日期：2002.1

  The bismuth nitrate-mediated guanidylation of N-benzoylthioureas was studied. This salt proved to be an effective guanylating reagent and allowed the obtention of N-benzoyl-guanidines in good yields. The methodology described is a promising alternative to the use of toxic HgCl2 in the synthesis of polysubstituted guanidines.

  研究了硝酸铋介导的N-苯甲酰硫脲的胍基化。该盐被证明是有效的胍基化试剂，并且可以良好的产率获得N-苯甲酰基-胍。所描述的方法是在合成多取代的胍类中使用有毒的HgCl 2的有前途的替代方法。
• The first bismuth(III)-catalyzed guanylation of thioureas
  作者：Silvio Cunha、Manoel T. Rodrigues

  DOI：10.1016/j.tetlet.2006.07.138

  日期：2006.9

  This work describes the first catalytic bismuth-promoted synthesis of polysubstituted guanidines in good yields through the guanylation reaction of Ar-benzoyl or N-phenylthioureas with primary and secondary amines, but now employing equimolar amounts of each organic reagent. Both bismuth iodine and bismuth nitrate were efficient as inorganic thiophiles at only 5 mol % in relation to substrates, being the first example of inorganic thiophiles acting in guanylation at catalytic levels. (c) 2006 Elsevier Ltd. All rights reserved.
• Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights
  作者：Simon Pape、Pablo Wessig、Heiko Brunner

  DOI：10.1021/acs.joc.6b00600

  日期：2016.6.3

  Recently we introduced iron trichloride as an environmentally benign and cost-efficient reagent for the synthesis of N-benzoylguanidines. This highly attractive synthetic approach grants access to a broad spectrum of N-benzoylguanidines under mild conditions in short reaction times. In this work we present an extended scope of Our methodology along with the results obtained from mechanistic studies via in situ IR spectroscopy in combination with LC (liquid chromatography)-MS analyses. On the basis of these new mechanistic insights we were able to optimize the synthetic protocol and to develop an alternative mechanistic proposal. In this context the symbiotic roles of iron trithloride and oxygen in the guanylation process are highlighted.
• DE68706
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  公开号：——

  公开（公告）日：——