7-benzoyl-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid | 93669-90-0

• 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: 7-benzoyl-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid
• 英文别名: 7-benzoyl-5-fluoro-2,3-dihydrobenzofuran-3-carboxylic acid
• CAS: 93669-90-0
• 化学式: C₁₆H₁₁FO₄
• 分子量: 286.259
• InChiKey: GQJXAPTWDCTBLF-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  501.1±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-氟-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 7-benzoyl-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid
  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

• 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。
• Benzofuran and benzothiophene-carboxylic-acid derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0117675A1

  公开（公告）日：1984-09-05

  Compounds of formula (I): wherein: Ar is phenyl optionally substituted in the o-, m-, or p-position by C1-4. alkyl, C1-4 alkoxy, trifluoromethyl, bromo, chloro or fluoro, pyrryl optionally N-substituted by C1-4 alkyl, 2-furyl or 2-thienyl either optionally substituted in the 3-, 4- or 5-position by methyl, chloro or bromo, or 3-furyl or 3-thienyl; X is oxygen, sulphur, sulphoxide or sulphone, Y is methylene, R1 and R3 are hydrogen or C1-4 alkyl, and R2 is hydrogen, C1-4 alkyl, fluoro, chloro or bromo, or X is methylene, Y is oxygen, R1 and R3 are both hydrogen, and R2 is hydrogen, fluoro, chloro or bromo; and R4 is hydrogen or C1-4 alkyl, or a salt thereof, have analgesic and/or anti-inflammatory activity.

  式(I)化合物： 其中 Ar 是在 o、m 或 p 位任选被 C1-4 烷基、C1-4 烷氧基、三氟甲基、溴、氯或氟取代的苯基、 由 C1-4 烷基任选 N 取代的吡咯基、 在 3-、4-或 5-位任选被甲基、氯或溴取代的 2-呋喃基或 2-噻吩基，或 3-呋喃基或 3-噻吩基； X 是氧、硫、亚砜或砜，Y 是亚甲基，R1 和 R3 是氢或 C1-4 烷基，R2 是氢、C1-4 烷基、氟、氯或溴，或 X 是亚甲基，Y 是氧，R1 和 R3 都是氢，R2 是氢、氟、氯或溴；以及 R4 是氢或 C1-4 烷基，或其盐，具有镇痛和/或消炎活性。
• 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：——
• US4548948A
  申请人：——

  公开号：US4548948A

  公开（公告）日：1985-10-22
• 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.