3-(3-fluorophenyl)isoxazole | 1093649-62-7

• 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: 3-(3-fluorophenyl)isoxazole
• 英文别名: 3-(3-Fluorophenyl)-1,2-oxazole
• CAS: 1093649-62-7
• 化学式: C₉H₆FNO
• 分子量: 163.151
• InChiKey: CQTKCUDXZKGASB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-fluorophenyl)isoxazole 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 1.0h， 以74%的产率得到2,6-bis(3-fluorophenyl)-3,7-diazatricyc[4.2.0.0(2,5)]octane-4,8-dione
  参考文献：
  名称：

  Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA

  摘要：

  3-Arylisoxazoles react with LDA in THF at 0 degrees C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.0(2,5)]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.063
• 作为产物：
  描述：

  3-(3-fluorophenyl)-5-hydroxy-2-isoxazoline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以78%的产率得到3-(3-fluorophenyl)isoxazole
  参考文献：
  名称：

  Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA

  摘要：

  3-Arylisoxazoles react with LDA in THF at 0 degrees C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.0(2,5)]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.063

文献信息

• 2-Fluorobenzenesulfonyl compounds for the treatment of inflammation
  申请人：Pharmacia Corporation

  公开号：US20020183362A1

  公开（公告）日：2002-12-05

  Methods of treating cyclooxygenase-2 mediated disorders comprising administering to a subject a therapeutically effective amount of one or more 2-fluorobenzenesulfonyl compounds corresponding to Formula I: 1 wherein A, R 1 , R 2 , and R 3 are as described in the specification, and novel 2 fluorobenzenesulfonyl compounds within Formula I.

  治疗环氧合酶-2介导的疾病的方法包括向受试者施用与公式I中对应的一种或多种2-氟苯磺酰化合物的治疗有效剂量：1其中A、R1、R2和R3如规范中所述，并且公式I内的新型2-氟苯磺酰化合物。
• 2-FLUOROBENZENESULFONYL COMPOUNDS FOR THE TREATMENT OF INFLAMMATION
  申请人：Pharmacia Corporation

  公开号：EP1296971A2

  公开（公告）日：2003-04-02
• HETEROARYL ALLOSTERIC MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS
  申请人：Merck Sharp & Dohme LLC

  公开号：EP3684357B1

  公开（公告）日：2022-12-28
• [EN] 2-FLUOROBENZENESULFONYL COMPOUNDS FOR THE TREATMENT OF INFLAMMATION<br/>[FR] COMPOSES DE 2-FLUOROBENZENESULFONYLE UTILISES POUR LE TRAITEMENT D'INFLAMMATIONS
  申请人：PHARMACIA CORP

  公开号：WO2001081332A2

  公开（公告）日：2001-11-01

  Methods of treating cyclooxygenase-2 mediated disorders comprising administering to a subject a therapeutically effective amount of one or more 2-fluorobenzenesulfonyl compounds corresponding to Formula (I) wherein A, R?1, R2, and R3¿ are as described in the specification, and novel 2-fluorobenzenesulfonyl compounds within Formula (I).
• Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA
  作者：Leonardo Di Nunno、Paola Vitale、Antonio Scilimati

  DOI：10.1016/j.tet.2008.09.063

  日期：2008.12

  3-Arylisoxazoles react with LDA in THF at 0 degrees C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.0(2,5)]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA. (C) 2008 Elsevier Ltd. All rights reserved.