5-hydroxy-3-(4-methylphenyl)-2-isoxazoline

• 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: 5-hydroxy-3-(4-methylphenyl)-2-isoxazoline
• 英文别名: 3-(4-Methylphenyl)-4,5-dihydro-1,2-oxazol-5-ol；3-(4-methylphenyl)-4,5-dihydro-1,2-oxazol-5-ol
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: WALZJXSTYTYYHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-(4-methylphenyl)-2-isoxazoline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以84%的产率得到3-对甲苯异噁唑
  参考文献：
  名称：

  受阻锂酰胺诱导的3-芳基异恶唑立体选择性二聚为笼状双-β-内酰胺类合成2,6-二芳基-3,7-二氮杂三环[4.2.0.0 2,5 ] octan -4,8-​​二酮

  摘要：

  3-Arylisoxazoles与受阻的锂酰胺反应生成顺式2,6-二芳基-3,7-二氮杂三环[4.2.0.0 2,5 ] octan -4,8-​​二酮，收率良好。通过X射线衍射分析确定所获得的笼状双β-内酰胺的立体化学。关于这种迄今未知分子的形成机理，提出了由Li +螯合立体诱导的氮杂环丁烷酮阴离子中间体的二聚化。

  DOI：

  10.1016/j.tet.2007.09.040
• 作为产物：
  描述：

  p-Methyl-zimtaldehyd 在 N-羟基-4-甲基苯磺酰胺 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以85%的产率得到5-hydroxy-3-(4-methylphenyl)-2-isoxazoline
  参考文献：
  名称：

  Efficient and Regioselective Synthesis of 5-Hydroxy-2-isoxazolines: Versatile Synthons for Isoxazoles, β-Lactams, and γ-Amino Alcohols

  摘要：

  An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy-2-isoxazolines, which have been proved to be versatile synthons for isoxazles, beta-hydroxy oximes, and gamma-amino alcohols. beta-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from beta-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.

  DOI：

  10.1021/jo1000065

文献信息

• Stereoselective dimerization of 3-arylisoxazoles to cage-shaped bis-β-lactams syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by hindered lithium amides
  作者：Leonardo Di Nunno、Paola Vitale、Antonio Scilimati、Laura Simone、Francesco Capitelli

  DOI：10.1016/j.tet.2007.09.040

  日期：2007.12

  Stereochemistry of the so-obtained cage-shaped bis-β-lactams was assigned by X-ray diffraction analysis. Concerning the mechanism of formation of such hitherto unknown molecules, dimerization of an azetinone anion intermediate stereoselectively induced by Li+ chelation is suggested.

  3-Arylisoxazoles与受阻的锂酰胺反应生成顺式2,6-二芳基-3,7-二氮杂三环[4.2.0.0 2,5 ] octan -4,8-​​二酮，收率良好。通过X射线衍射分析确定所获得的笼状双β-内酰胺的立体化学。关于这种迄今未知分子的形成机理，提出了由Li +螯合立体诱导的氮杂环丁烷酮阴离子中间体的二聚化。
• Bifunctional heterocyclic compounds and methods of making and using same
  申请人：Wang Deping

  公开号：US20080119419A1

  公开（公告）日：2008-05-22

  The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional heterocyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.

  本发明提供了一系列双功能杂环化合物，可作为抗感染、抗增殖、抗炎和促动力药物使用。本发明还提供了制备双功能杂环化合物的方法，以及使用这些化合物作为抗感染、抗增殖剂、抗炎剂和/或促动力剂的方法。
• 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.
• Efficient and Regioselective Synthesis of 5-Hydroxy-2-isoxazolines: Versatile Synthons for Isoxazoles, β-Lactams, and γ-Amino Alcohols
  作者：Shibing Tang、Jinmei He、Yongquan Sun、Liuer He、Xuegong She

  DOI：10.1021/jo1000065

  日期：2010.3.19

  An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy-2-isoxazolines, which have been proved to be versatile synthons for isoxazles, beta-hydroxy oximes, and gamma-amino alcohols. beta-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from beta-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.