N-(5-bromo-2-oxo-2H-chromen-6-yl)-4-methylbenzamide | 1365540-09-5

• 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: N-(5-bromo-2-oxo-2H-chromen-6-yl)-4-methylbenzamide
• CAS: 1365540-09-5
• 化学式: C₁₇H₁₂BrNO₃
• 分子量: 358.191
• InChiKey: LDRMUWMAQPERHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.31
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-2-oxo-2H-chromen-6-yl)-4-methylbenzamide 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以92%的产率得到2-p-tolyl-7H-chromeno[6,5-d]oxazol-7-one
  参考文献：
  名称：

  Catalyst-free synthesis of coumarin-, quinolone- and pyridine-annulated oxazole derivatives

  摘要：

  An efficient approach for the synthesis of coumarin-, quinolone- and pyridine-annulated oxazole derivatives has been achieved by direct base-mediated intramolecular carbon-oxygen bond formation in a transition metal catalyst-free protocol. Intramolecular cyclization of o-bromoamides in DMSO in the presence of Cs2CO3 at 130 degrees C affords heterocycle-annulated oxazole derivatives in high yields via a nucleophilic ;addition of amide to form the C-O bond. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.01.015
• 作为产物：
  描述：

  6-amino-5-bromo-2H-chromen-2-one 、 对甲基苯甲酰氯 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以82%的产率得到N-(5-bromo-2-oxo-2H-chromen-6-yl)-4-methylbenzamide
  参考文献：
  名称：

  Catalyst-free synthesis of coumarin-, quinolone- and pyridine-annulated oxazole derivatives

  摘要：

  An efficient approach for the synthesis of coumarin-, quinolone- and pyridine-annulated oxazole derivatives has been achieved by direct base-mediated intramolecular carbon-oxygen bond formation in a transition metal catalyst-free protocol. Intramolecular cyclization of o-bromoamides in DMSO in the presence of Cs2CO3 at 130 degrees C affords heterocycle-annulated oxazole derivatives in high yields via a nucleophilic ;addition of amide to form the C-O bond. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.01.015

文献信息

• An efficient synthesis of coumarin- and quinolone-annulated thiazole derivatives via ligand-free iron (III)-catalyzed coupling followed by acid-promoted condensation
  作者：K.C. Majumdar、Debankan Ghosh

  DOI：10.1016/j.tetlet.2013.06.017

  日期：2013.8

  An efficient strategy for the synthesis of coumarin- and quinolone-annulated thiazole derivatives using sodium sulfide as a sulfur source has been achieved via ligand-free iron (III)-catalyzed coupling followed by acid-promoted condensation. This synthetic protocol is one-pot, less expensive, and affords the products in good yields. (C) 2013 Elsevier Ltd. All rights reserved.