6-methylcoumarin-3-N-phenylcarbamide | 38485-81-3

• 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: 6-methylcoumarin-3-N-phenylcarbamide
• 英文别名: N-phenyl-6-methylcoumarin-3-carboxamide；6-Methylcumarin-3-carbonsaeure-anilid；N-phenyl-6-methyl-2-oxo-2H-1-benzopyran-3-carboxamide；6-methyl-2-oxo-2H-chromene-3-carboxylic acid anilide；6-methyl-2-oxo-N-phenyl-2H-chromene-3-carboxamide；6-methyl-2-oxo-N-phenylchromene-3-carboxamide
• CAS: 38485-81-3
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: JUQDUATUBQVGDN-UHFFFAOYSA-N

物化性质

• 沸点：
  544.8±50.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲基水杨醛 在 嘧啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 6-methylcoumarin-3-N-phenylcarbamide
  参考文献：
  名称：

  Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?

  摘要：

  Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumarin- and chomone-3-phenylcarboxamide scaffolds. Compounds 10a and 10b were the most potent, selective, and reversible noncompetitive IMAO-B. The benzopyrone sp(2) oxygen atom was found to be position independent and a productive contributor for the ligand-enzyme complex stability.

  DOI：

  10.1021/acs.jmedchem.7b00918

文献信息

• Methyl Esters as Cross-Coupling Electrophiles: Direct Synthesis of Amide Bonds
  作者：Yan-Long Zheng、Stephen G. Newman

  DOI：10.1021/acscatal.9b00884

  日期：2019.5.3

  metal-catalyzed cross-coupling are two of the most frequently used chemical reactions in organic synthesis. Recently, an overlap between these two reaction families was identified when Pd and Ni catalysts were demonstrated to cleave the strong C–O bond present in esters via oxidative addition. When simple methyl and ethyl esters are used, this transformation provides a powerful alternative to classical amide bond

  酰胺键的形成和过渡金属催化的交叉偶联是有机合成中最常用的两种化学反应。最近，当Pd和Ni催化剂通过氧化加成裂解酯中存在的强C-O键时，发现这两个反应族之间存在重叠。当使用简单的甲酯和乙酯时，这种转化为经典的酰胺键形成提供了有力的替代方法，后者通常具有化学计量活化剂的特征。迄今为止，几乎没有氧化还原活性催化剂被证明可以激活烷基酯的C（酰基）-O键，这使得当需要优化具有挑战性的反应时，很难进行明智的筛选。我们证明了带有多种NHC，磷化氢，
• Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives
  作者：L Bonsignore、G Loy、D Secci、A Calignano

  DOI：10.1016/0223-5234(93)90020-f

  日期：1993.1

  Continuing our research on the synthesis and biological activity of heterocyclic compounds synthesized by carbon suboxide, we prepared and screened some 2-oxo (2H) 1-benzopyran-3-carboxamide derivatives. The results of pharmacological assays are reported and discussed.
• Novel 3-Carboxamide-coumarins as Potent and Selective FXIIa Inhibitors
  作者：Séverine Robert、Carine Bertolla、Bernard Masereel、Jean-Michel Dogné、Lionel Pochet

  DOI：10.1021/jm8002697

  日期：2008.6.1

  Recently, FXIIa was highlighted as an original attractive target for the development of new anticoagulant drugs with low rates of therapy-related hemorrhages. In this work, we describe the development of a new series of 3-carboxamide-coumarins that are the first potent and selective nonpeptidic inhibitors of FXIIa.
• Elkasaby, M. A.; Noureldin, N. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 12, p. 1080 - 1081
  作者：Elkasaby, M. A.、Noureldin, N. A.

  DOI：——

  日期：——
• Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?
  作者：André Fonseca、Joana Reis、Tiago Silva、Maria João Matos、Donatella Bagetta、Francesco Ortuso、Stefano Alcaro、Eugenio Uriarte、Fernanda Borges

  DOI：10.1021/acs.jmedchem.7b00918

  日期：2017.8.24

  Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumarin- and chomone-3-phenylcarboxamide scaffolds. Compounds 10a and 10b were the most potent, selective, and reversible noncompetitive IMAO-B. The benzopyrone sp(2) oxygen atom was found to be position independent and a productive contributor for the ligand-enzyme complex stability.