5-fluoro-2,3-dihydrobenzofuran-3-carboxylic acid | 93670-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-fluoro-2,3-dihydrobenzofuran-3-carboxylic acid
• 英文别名: 5-Fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid
• CAS: 93670-19-0
• 化学式: C₉H₇FO₃
• mdl: MFCD10696206
• 分子量: 182.151
• InChiKey: RUVNVSVZHFURDN-UHFFFAOYSA-N

物化性质

• 沸点：
  305.9±42.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-2,3-dihydrobenzofuran-3-carboxylic acid 在 盐酸 、 三氯化铝 作用下， 以 二硫化碳 为溶剂， 反应 73.5h， 生成 ethyl 7-benzoyl-5-fluoro-2,3-dihydrobenzofuran-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
• 作为产物：
  描述：

  6-氟-4-二氢色原酮 在 thallium(III) nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 5-fluoro-2,3-dihydrobenzofuran-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

• Anti-inflammatory and analgesic benzothiophene and benzafuran
  申请人：Beecham Group p.l.c.

  公开号：US04548948A1

  公开（公告）日：1985-10-22

  Compounds of formula (I): ##STR1## wherein: Ar is phenyl optionally substituted in the o-, m- or p-position by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, bromo, chloro or fluoro, pyrryl optionally N-substituted by C.sub.1-4 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, R.sub.1 and R.sub.3 are hydrogen or C.sub.1-4 alkyl, and R.sub.2 is hydrogen, C.sub.1-4 alkyl, fluoro, chloro or bromo, or X is methylene, Y is oxygen, R.sub.1 and R.sub.3 are both hydrogen, and R.sub.2 is hydrogen, fluoro, chloro or bromo; and R.sub.4 is hydrogen or C.sub.1-4 alkyl, or a salt thereof, have analgesic and/or anti-inflammatory activity.

  式(I)的化合物：## STR1 ## 其中：Ar是苯基，可以在o-、m-或p-位置上被C.sub.1-4烷基，C.sub.1-4烷氧基，三氟甲基，溴，氯或氟取代，也可以是吡咯基，可选择由C.sub.1-4烷基取代，2-呋喃基或2-噻吩基，也可以在3-、4-或5-位置上被甲基，氯或溴取代，或3-呋喃基或3-噻吩基；X是氧，硫，亚砜或砜，Y是亚甲基，R.sub.1和R.sub.3是氢或C.sub.1-4烷基，R.sub.2是氢，C.sub.1-4烷基，氟，氯或溴，或X是亚甲基，Y是氧，R.sub.1和R.sub.3都是氢，R.sub.2是氢，氟，氯或溴；R.sub.4是氢或C.sub.1-4烷基，或其盐，具有镇痛和/或抗炎活性。
• 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。
• 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.