N¹-(4-Methoxy-phenyl)-N³-benzoyl-guanidin | 101091-38-7

• 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: N¹-(4-Methoxy-phenyl)-N³-benzoyl-guanidin
• 英文别名: N-[N'-(4-methoxyphenyl)carbamimidoyl]benzamide
• CAS: 101091-38-7
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: CXTBWQWHNFKMFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  76.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-anisyl)-N'-benzoylthiourea 在 氨 、 碘 、 三乙胺 作用下， 反应 4.0h， 以92%的产率得到N¹-(4-Methoxy-phenyl)-N³-benzoyl-guanidin
  参考文献：
  名称：

  Iodine-Mediated Multi-Component Reactions: Readily Access to Tetrazoles and Guanidines

  摘要：

  摘要：苯甲酰氯与胺的一锅式顺序反应，随后在碱性条件下处理分子I2试剂，以中等至优良的产率提供苯甲酰四唑和胍胺。这种一锅式合成具有多个优点，如温和的反应条件、短的反应时间、方便的处理、高产率，使用廉价且易获得的试剂分子碘。此外，功能团容忍性已经得到探索。

  DOI：

  10.2174/1570178617999200728212116

文献信息

• A new and environmentally benign synthesis of aroylguanidines using iron trichloride
  作者：Simon Pape、Pablo Wessig、Heiko Brunner

  DOI：10.1039/c5ra20869f

  日期：——

  A new synthetic approach for the guanylation of aroylthioureas using iron trichloride is presented. Our synthetic method distinguishes itself by benign reaction conditions, low costs and a broad product spectrum. The scope of the reaction and calorimetric studies are described.

  提出了一种新的合成方法，用于使用三氯化铁对芳硫基硫脲进行鸟嘌呤化。我们的合成方法以其良好的反应条件，低成本和广泛的产品范围而独树一帜。描述了反应的范围和量热研究。
• 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.
• Exploring the antileishmanial activity of <i>N</i>¹,<i>N</i>²-disubstituted-benzoylguanidines: synthesis and molecular modeling studies
  作者：Kaio Maciel de Santiago-Silva、Bruna Taciane da Silva Bortoleti、Tiago de Oliveira Brito、Ivete Conchon Costa、Camilo Henrique da Silva Lima、Fernando Macedo、Milena Menegazzo Miranda-Sapla、Wander Rogério Pavanelli、Marcelle de Lima Ferreira Bispo

  DOI：10.1080/07391102.2021.1959403

  日期：2022.12.12
• A simple one-pot methodology for the synthesis of substituted benzoylguanidines from benzoylthioureas using tert-butyl hydroperoxide
  作者：Henrique Esteves、Ângelo de Fátima、Rosane de P. Castro、José R. Sabino、Fernando Macedo、Tiago Oliveira Brito

  DOI：10.1016/j.tetlet.2015.10.088

  日期：2015.12

  The potential of tert-butyl hydroperoxide as a reagent in the guanylation of benzoylthioureas in the presence of amines has been evaluated in a systematic study involving substrates bearing N-2-substituents with different electronic properties. The results show that (BuOOH)-Bu-t is a suitable and robust reagent for the synthesis of either N-1,N-2,N-3-tri- and tetrasubstituted or N-1,N-2-disubstituted guanidines from N-2-substituted N-1-benzoylthioureas and N-1-benzoylthioureas, respectively. The recrystallised guanylation adducts were readily obtained in good yields and at high purity levels after a simple one-pot reaction procedure. The crystal structures of two novel benzoylguanidines are provided. (C) 2015 Elsevier Ltd. All rights reserved.