4-methoxybenzo[b]thiophene-5-carboxylic acid methyl ester | 849100-51-2

• 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: 4-methoxybenzo[b]thiophene-5-carboxylic acid methyl ester
• 英文别名: Methyl 4-methoxy-1-benzothiophene-5-carboxylate；methyl 4-methoxy-1-benzothiophene-5-carboxylate
• CAS: 849100-51-2
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: DBCDSJGCKRLKRC-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  350.6±22.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxybenzo[b]thiophene-5-carboxylic acid methyl ester 在 镍 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.75h， 生成
  参考文献：
  名称：

  An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones

  摘要：

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.111
• 作为产物：
  描述：

  4-羟基-苯并[b]噻吩-5-羧酸甲酯 、 碘甲烷 在 potassium hydrogencarbonate 作用下， 以 丙酮 为溶剂， 以90%的产率得到4-methoxybenzo[b]thiophene-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 4-hydroxy-1-methylindole and benzo[b]thiophen-4-ol based unnatural flavonoids as new class of antimicrobial agents☆

  摘要：

  Synthesis of nitrogen and sulfur heterocyclic mimics of furanoflavonoids have been achieved for the first time. Synthesized flavonoid alkaloids and thiophenyl flavonoids have been screened for antifungal and antibacterial activities. All the test compounds barring 25 exhibited antifungal activity. The compound 19 was the best and showed comparable MICs to the known compound karanjin. Compounds 5, 12, 14 and 22 also showed comparable MIC to karanjin. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.032

文献信息

• Synthesis of 4-hydroxy-1-methylindole and benzo[b]thiophen-4-ol based unnatural flavonoids as new class of antimicrobial agents☆
  作者：Prem P. Yadav、Prasoon Gupta、A.K. Chaturvedi、P.K. Shukla、Rakesh Maurya

  DOI：10.1016/j.bmc.2004.12.032

  日期：2005.3.1

  Synthesis of nitrogen and sulfur heterocyclic mimics of furanoflavonoids have been achieved for the first time. Synthesized flavonoid alkaloids and thiophenyl flavonoids have been screened for antifungal and antibacterial activities. All the test compounds barring 25 exhibited antifungal activity. The compound 19 was the best and showed comparable MICs to the known compound karanjin. Compounds 5, 12, 14 and 22 also showed comparable MIC to karanjin. (C) 2005 Elsevier Ltd. All rights reserved.
• An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones
  作者：Prem P. Yadav、Ghufran Ahmad、Rakesh Maurya

  DOI：10.1016/j.tetlet.2005.06.111

  日期：2005.8

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.