methyl 7-benzoyl-5-chloro-2,3-dihydro-1-benzofuran-3-carboxylate | 101166-62-5

• 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: methyl 7-benzoyl-5-chloro-2,3-dihydro-1-benzofuran-3-carboxylate
• CAS: 101166-62-5
• 化学式: C₁₇H₁₃ClO₄
• 分子量: 316.741
• InChiKey: HRLOHBLOFYMACR-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C
• 沸点：
  469.8±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  methyl 7-benzoyl-5-chloro-2,3-dihydro-1-benzofuran-3-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以95%的产率得到7-benzoyl-5-chloro-2,3-dihydrobenzofuran-3-carboxylic acid
  参考文献：
  名称：

  潜在的COX抑制剂BRL-37959和涉及铋（III）的类似物催化的Friedel-Crafts酰化反应的简明合成。

  摘要：

  我们报告了一种合成可能的环氧合酶（COX）抑制剂BRL-37959的简洁方法的发展，据信这是一种有效的非甾体类抗炎药（NSAID）。四步合成大大提高了由市售水杨醛生产化合物的效率。合成涉及优化的三氟甲磺酸铋（III）催化的苯并呋喃环的苯甲酰化。

  DOI：

  10.1002/cbdv.201800334
• 作为产物：
  描述：

  6-氯-4-二氢色原酮 在 盐酸 、 三氯化铝 、 sodium carbonate 、 thallium(III) nitrate 作用下， 以 二硫化碳 、 乙醇 、 二氯甲烷 为溶剂， 反应 77.5h， 生成 methyl 7-benzoyl-5-chloro-2,3-dihydro-1-benzofuran-3-carboxylate
  参考文献：
  名称：

  7-Aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids as analgesic agents

  摘要：

  The synthesis of a series of 7-aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids is described. The isomeric 4-benzoyl-1,3-dihydrobenzo[c]furan-1-carboxylic acid was also prepared. Compounds were evaluated for analgesic activity in the mouse phenyl-p-quinone-induced writhing test. Selected compounds were tested for their ability to produce gastric damage in fasted mice and for inhibition of prostaglandin synthetase activity in vitro. Zomepirac was used as a reference. Structure-activity relationships are discussed. One of the compounds, 7-benzoyl-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (2c), combined potent analgesic activity with low gastric irritancy.

  DOI：

  10.1021/jm00156a004

文献信息

• BOYLE E. A.; MANGAN F. R.; MARKWELL R. E.; SMITH S. A.; THOMSON M. J.; WA+, J. MED. CHEM., 29,(1986) N 6, 894-898
  作者：BOYLE E. A.、 MANGAN F. R.、 MARKWELL R. E.、 SMITH S. A.、 THOMSON M. J.、 WA+

  DOI：——

  日期：——
• A Concise Synthesis of Potential COX Inhibitor BRL-37959 and Analogs Involving Bismuth(III) Catalyzed Friedel−Crafts Acylation
  作者：Shamsul Arefin Ahmed、Damon J. Hinz、Marcus J. Jellen、M. Mahmun Hossain

  DOI：10.1002/cbdv.201800334

  日期：2018.12

  cyclooxygenase (COX) inhibitor BRL-37959, which is believed to be a potent nonsteroidal anti-inflammatory drug (NSAID). The four-step synthesis greatly increased the efficiency of compound production from commercially available salicylaldehydes. The synthesis involved an optimized, bismuth(III) trifluoromethanesulfonate catalyzed benzoylation of a benzofuran ring.

  我们报告了一种合成可能的环氧合酶（COX）抑制剂BRL-37959的简洁方法的发展，据信这是一种有效的非甾体类抗炎药（NSAID）。四步合成大大提高了由市售水杨醛生产化合物的效率。合成涉及优化的三氟甲磺酸铋（III）催化的苯并呋喃环的苯甲酰化。
• 7-Aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids as analgesic agents
  作者：Elizabeth A. Boyle、Frank R. Mangan、Roger E. Markwell、Stephen A. Smith、Michael J. Thomson、Robert W. Ward、Paul A. Wyman

  DOI：10.1021/jm00156a004

  日期：1986.6

  The synthesis of a series of 7-aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids is described. The isomeric 4-benzoyl-1,3-dihydrobenzo[c]furan-1-carboxylic acid was also prepared. Compounds were evaluated for analgesic activity in the mouse phenyl-p-quinone-induced writhing test. Selected compounds were tested for their ability to produce gastric damage in fasted mice and for inhibition of prostaglandin synthetase activity in vitro. Zomepirac was used as a reference. Structure-activity relationships are discussed. One of the compounds, 7-benzoyl-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (2c), combined potent analgesic activity with low gastric irritancy.