3-bromo-4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one | 1227925-62-3

• 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-bromo-4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one
• 英文别名: 3-bromo-4-methyl-7-(2-oxo-propoxy)-chromen-2-one；3-Bromo-4-methyl-7-(2-oxopropoxy)chromen-2-one
• CAS: 1227925-62-3
• 化学式: C₁₃H₁₁BrO₄
• 分子量: 311.132
• InChiKey: YSIPIAXHWAZFDU-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  449.3±45.0 °C(Predicted)
• 密度：
  1.543±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one 在 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 3,5-dimethyl-N-phenylbenzo[1,2-b:5,4-b']difuran-2-carboxamide
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid

  摘要：

  We have synthesized various amide derivatives of benzodifuran-2-carboxylic acid from resorcinol. Reaction of 7-hydroxy-4-methylcoumarin with chloroacetone in anhydrous K2CO3 and dry acetone gave ether derivative of 7-hydroxy-4-methylcoumarin 3 which on reaction with N-bromosuccinimide in chloroform gave corresponding 3-bromo derivative 4. Cyclization of bromo derivative in 10% ethanolic KOH gave benzodifuran-2-carboxylic acid 5. This acid was converted into acid chloride using oxalyl chloride and then substituted with different amines in presence of base, triethylamine to give amide derivatives of benzodifuran-2-carboxylic acid 6. All compounds were screened for antimicrobial activity against two Gram positive bacteria Staphylococus aureus and Bacillus subtilis, two Gram negative bacteria E. coli and P. aeruginosa and one fungus Candida albicans. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.026
• 作为产物：
  描述：

  羟甲香豆素 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 12.0h， 生成 3-bromo-4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid

  摘要：

  We have synthesized various amide derivatives of benzodifuran-2-carboxylic acid from resorcinol. Reaction of 7-hydroxy-4-methylcoumarin with chloroacetone in anhydrous K2CO3 and dry acetone gave ether derivative of 7-hydroxy-4-methylcoumarin 3 which on reaction with N-bromosuccinimide in chloroform gave corresponding 3-bromo derivative 4. Cyclization of bromo derivative in 10% ethanolic KOH gave benzodifuran-2-carboxylic acid 5. This acid was converted into acid chloride using oxalyl chloride and then substituted with different amines in presence of base, triethylamine to give amide derivatives of benzodifuran-2-carboxylic acid 6. All compounds were screened for antimicrobial activity against two Gram positive bacteria Staphylococus aureus and Bacillus subtilis, two Gram negative bacteria E. coli and P. aeruginosa and one fungus Candida albicans. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.026

文献信息

• Studies in synthesis of new psoralenamines
  作者：Jagdish M. Patel、Shubhangi S. Soman

  DOI：10.1002/jhet.327

  日期：——

  New amino psoralen derivatives have been synthesized via bromination. Bromination of 3,5‐substituted psoralens has been studied. The second position of the furan ring is more susceptible to bromination than the α‐position of the chromen‐2‐one ring in psoralens. Hence, the target psoralenamines were synthesized starting with 3‐bromo‐7‐hydroxy‐4‐methyl‐chromen‐2‐one, which was condensed with different

  通过溴化合成了新的氨基补骨脂素衍生物。已经研究了3,5-取代的补骨脂素的溴化。呋喃环的第二个位置比补骨脂素中的chromen-2-one环的α-位置更容易被溴化。因此，目标补骨脂胺是从3-溴-7-羟基-4-甲基-铬烯-2-酮开始合成的，然后与不同的α-卤代酮缩合，然后在乙醇氢氧化钾中环化，得到所需的6-溴补骨脂素。 ，最终被转化为补骨脂素。J.杂环化​​学。（2010）。
• Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid
  作者：Jigar N. Soni、Shubhangi S. Soman

  DOI：10.1016/j.ejmech.2014.01.026

  日期：2014.3

  We have synthesized various amide derivatives of benzodifuran-2-carboxylic acid from resorcinol. Reaction of 7-hydroxy-4-methylcoumarin with chloroacetone in anhydrous K2CO3 and dry acetone gave ether derivative of 7-hydroxy-4-methylcoumarin 3 which on reaction with N-bromosuccinimide in chloroform gave corresponding 3-bromo derivative 4. Cyclization of bromo derivative in 10% ethanolic KOH gave benzodifuran-2-carboxylic acid 5. This acid was converted into acid chloride using oxalyl chloride and then substituted with different amines in presence of base, triethylamine to give amide derivatives of benzodifuran-2-carboxylic acid 6. All compounds were screened for antimicrobial activity against two Gram positive bacteria Staphylococus aureus and Bacillus subtilis, two Gram negative bacteria E. coli and P. aeruginosa and one fungus Candida albicans. (C) 2014 Elsevier Masson SAS. All rights reserved.