3-[2-(三氟甲基)苯基]异恶唑 | 1093649-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[2-(三氟甲基)苯基]异恶唑
• 英文名称: 3-[2-(trifluoromethyl)phenyl]isoxazole
• 英文别名: 3-(2-(Trifluoromethyl)phenyl)isoxazole；3-[2-(trifluoromethyl)phenyl]-1,2-oxazole
• CAS: 1093649-63-8
• 化学式: C₁₀H₆F₃NO
• 分子量: 213.159
• InChiKey: DXKYLEWWXZLQEY-UHFFFAOYSA-N

物化性质

• 沸点：
  289.6±40.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(三氟甲基)苯基]异恶唑 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 1.0h， 以30%的产率得到2,6-bis-3-(2-(trifluoromethyl)phenyl)-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-(2-(trifluoromethyl)phenyl)-5-hydroxy-2-isoxazoline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以74%的产率得到3-[2-(三氟甲基)苯基]异恶唑
  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

• NOVEL COMPOUNDS
  申请人：Barlaam Bernard

  公开号：US20120095011A1

  公开（公告）日：2012-04-19

  The invention provides compounds of formula in which R 1 , R 2 , R 3 and R 4 have the meanings defined in the specification; processes for their preparation; pharmaceutical compositions containing them; a process for preparing the pharmaceutical compositions; and their use in therapy.

  本发明提供的化合物具有公式，其中R1，R2，R3和R4具有规范中定义的含义；制备它们的过程；包含它们的制药组合物；制备制药组合物的过程；以及它们在治疗中的使用。
• 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.