3-benzoylamino-8-hydroxycoumarin | 126325-43-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-benzoylamino-8-hydroxycoumarin
• 英文别名: N-(8-hydroxy-2-oxo-2H-chromen-3-yl)benzamide；N-(8-hydroxy-2-oxochromen-3-yl)benzamide
• CAS: 126325-43-7
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: CULKOVNSQGQBOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-benzoylamino-8-hydroxycoumarin 在 sodium acetate 作用下， 生成 Acetic acid 3-benzoylamino-2-oxo-2H-chromen-8-yl ester
  参考文献：
  名称：

  Thiol-induced conversion of (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-ones into 3-benzoylaminocoumarins

  摘要：

  Toluene-alpha-thiol induces cleavage of the 1,5-bond of (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-ones in triethylamine-containing ethanol to give 3-benzoylaminocoumarins

  DOI：

  10.1039/p19910002611
• 作为产物：
  描述：

  N-(5,6,7,8-tetrahydro-2,5-dioxo-2H-1-benzopyran-3-yl)benzamide 在 氧气 、 甲烷 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以7%的产率得到3-benzoylamino-8-hydroxycoumarin
  参考文献：
  名称：

  Oxydehydrogenative aromatization of fused 3-aminopyran-2-ones on carbon surfaces: a simple approach towards 3-amino-5-hydroxycoumarin derivatives

  摘要：

  Aromatization of selected 3-acylamino-5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones, yielding the corresponding 3-acylamino-5-hydroxycoumarins, was achieved by dehydrogenation with molecular oxygen in the presence of activated carbon. The use of nonpolar solvents and high temperatures was crucial for attaining satisfactory conversions. The 3-benzoylamino-5,6,7,8-tetrahydrocoumarin without a 5-keto group and the 8-oxo analogue as well as the 5-oxo-5,6,7,8-tetrahydrocoumarins containing a free 3-amino group were less efficiently aromatized..

  DOI：

  10.1007/s00706-014-1227-4

文献信息

• Mukerjee, Arya K.; Rao, Laxmi; Homami, Seyed Saied, Canadian Journal of Chemistry, 1994, vol. 72, # 5, p. 1383 - 1387
  作者：Mukerjee, Arya K.、Rao, Laxmi、Homami, Seyed Saied、Joseph, Kiran

  DOI：——

  日期：——
• Jain, Archana; Mukerjee, Arya K., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 3, p. 493 - 496
  作者：Jain, Archana、Mukerjee, Arya K.

  DOI：——

  日期：——
• A one-pot [Bmim]OH-mediated synthesis of 3-benzamidocoumarins
  作者：Lal Dhar S. Yadav、Santosh Singh、Vijai K. Rai

  DOI：10.1016/j.tetlet.2009.02.166

  日期：2009.5

  The first example of an ionic liquid-promoted one-pot synthesis of 3-benzamidocoumarins from salicylaldehydes and 2-pheny-1,3-oxazolan-5-one via Knoevenagel condensation-ring transformation cascades has been reported. No by-product formation, operational simplicity, ambient temperature and high yield (85-97%) are the salient features of the present synthetic protocol. After isolation of the product, the ionic liquid, [Bmim]OH can be easily recycled for further use without any loss of efficiency. (C) 2009 Elsevier Ltd. All rights reserved.
• JAIN, ARCHANA;MUKERJEE, ARYA K., J. PRAKT. CHEM., 331,(1989) N, C. 493-496
  作者：JAIN, ARCHANA、MUKERJEE, ARYA K.

  DOI：——

  日期：——
• Mukerjee Arya K., Rao Laxmi, Homami Seyed Saied, Joseph Kiran, Can. J. Chem, 72 (1994) N 5, S 1383-1387
  作者：Mukerjee Arya K., Rao Laxmi, Homami Seyed Saied, Joseph Kiran

  DOI：——

  日期：——