3-methoxy-5-phenylisoxazole | 942-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-5-phenylisoxazole
• 英文别名: 3-methoxy-5-phenyl-isoxazole；3-hydroxymethyl-5-phenylisoxazole；3-Methoxy-5-phenyl-isoxazol-(3)；3-Methoxy-5-phenylisoxazolin；3-Aethoxy-5-phenyl-isoxazol；3-Methoxy-5-phenyl-isoxazol；3-Methoxy-5-phenyl-1,2-oxazole
• CAS: 942-68-7
• 化学式: C₁₀H₉NO₂
• mdl: MFCD00464108
• 分子量: 175.187
• InChiKey: NSCBMBLDRBRNFA-UHFFFAOYSA-N

物化性质

• 熔点：
  69-71 °C(Solv: hexane (110-54-3))
• 沸点：
  311.0±22.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-5-phenylisoxazole 在 正丁基锂 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 反应 8.5h， 生成 (3-Methoxy-5-phenyl-isoxazol-4-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Evaluation and synthesis of amino-hydroxy isoxazoles and pyrazoles as potential glycine agonists

  摘要：

  Except for structurally similar small amino acids, such as alanine, beta-alanine, and serine, compounds acting as glycine-receptor agonists are an unknown class of pharmacological agents. To investigate the potential of small, substituted heterocycles to act as glycine agonists, we have evaluated the similarities between glycine and a series of hydroxy- and amino-substituted pyrazoles and isoxazoles through complementary molecular modeling techniques. Using a "scorecard approach" to determine the overall similarity of projected agonist structures to glycine, we prioritized synthesis and subsequently prepared several novel derivatives. The biological activity of these compounds was compared to that of glycine by using a [3H]strychnine-mediated glycine receptor binding assay. Despite the close similarity in the calculated parameters when compared to glycine, no significant receptor-binding activity was observed for the targeted analogues. These results illustrate the structurally exacting nature of the glycine receptor.

  DOI：

  10.1021/jm00129a016
• 作为产物：
  描述：

  3-溴-5-苯基异噁唑 在 氢氧化钾 作用下， 以 甲醇 、 正己烷 、 水 为溶剂， 以77%的产率得到3-methoxy-5-phenylisoxazole
  参考文献：
  名称：

  Process for the preparation of 3,5-disubstituted isoxazoles

  摘要：

  提供了一种制备3-溴-和3-氯-5-取代异噁唑的新工艺。在（i）至少等摩尔量的碱性碳酸钠和碳酸氢钾的类别中选择碱性碱，与二溴甲酰肟或二氯甲酰肟一起，在惰性溶剂中，在室温下与化学式为R-C.tbd.CH的1-炔基衍生物的过量反应，其中R为氢，苯基或1-6 C烷基，可选地被卤素，OH，OR'，CHO，COR'，COOR'，CONH.sub.2，CONR'R"或NHCOR'取代，其中R'和R"可以相同或不同，是1-6 C烷基或卤代烷基。

  公开号：

  US04772719A1

文献信息

• Studies in isoxazole chemistry. III. The preparation and lithiation of 3,5-disubstituted isoxazoles
  作者：R. G. Micetich、C. G. Chin

  DOI：10.1139/v70-226

  日期：1970.5.1

  3-Arylisoxazol-5-ones and 5-arylisoxazol-3-ones were prepared and converted to the N-methyl and O-methyl derivatives by reaction with diazomethane. The halogen in 3-phenyl-5-chloroisoxazole was replaced by several alkoxy and thioalkoxy groups. The 3,5-disubstituted isoxazoles thus obtained reacted with n-butyllithium to form the 4-lithio derivatives, as shown by conversion to 4-carboxylic acids and 4-iodocompounds. 3-Methoxy-5-phenylisothiazole was also lithiated at the 4-position.

  3-芳基异噁唑-5-酮和5-芳基异噁唑-3-酮通过与重氮甲烷反应制备并转化为N-甲基和O-甲基衍生物。 3-苯基-5-氯异噁唑中的卤素被若干烷氧基和硫代烷氧基基团取代。得到的3,5-二取代异噁唑与正丁基锂反应形成4-锂衍生物，通过转化为4-羧酸和4-碘化合物得到证实。3-甲氧基-5-苯基异硫唑也在4-位进行锂化。
• EP1731513
  申请人：——

  公开号：——

  公开（公告）日：——
• Cabiddu,S.; Solinas,V., Gazzetta Chimica Italiana, 1969, vol. 99, p. 1107 - 1114
  作者：Cabiddu,S.、Solinas,V.

  DOI：——

  日期：——
• Bravo,P. et al., Gazzetta Chimica Italiana, 1961, vol. 91, p. 47 - 64
  作者：Bravo,P. et al.

  DOI：——

  日期：——
• Cabiddu,S. et al., Gazzetta Chimica Italiana, 1962, vol. 92, p. 501 - 518
  作者：Cabiddu,S. et al.

  DOI：——

  日期：——