3-苯基-5-甲硫基异恶唑 | 25755-80-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-苯基-5-甲硫基异恶唑
• 英文名称: 3-phenyl-5-methylthio-isoxazole
• 英文别名: 5-Methylthio-3-phenylisoxazole；5-methylsulfanyl-3-phenyl-isoxazole；3-Phenyl-5-methylmercaptoisoxazol；3-Phenyl-5-(methylthio)isoxazol；5-Methylsulfanyl-3-phenyl-1,2-oxazole
• CAS: 25755-80-0
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: CCUUBLRAMGCOOB-UHFFFAOYSA-N

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：
  51.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-苯基-5-甲硫基异恶唑 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 17.0h， 生成 5-(Methylsulfonyl)-3-phenylisoxazol
  参考文献：
  名称：

  Isoxazole anthelmintics

  摘要：

  A series of 3-halo-5-phenyl- and 3-phenyl-5-haloisoxazoles has demonstrated anthelmintic activity at doses ranging from 16 to 500 mg/kg orally against the rat roundworm, Nippostrongylus braziliensis. In the 5-phenyl series a halogen at the 3 position of the isoxazole ring was required for activity. However, in the 3-phenyl series activity was maintained after replacement of the 5-halogen with certain alkoxyl, thioalkoxyl, or amino groups. The 3-phenyl and 5-phenyl series apparently are not acting biologically at a common receptor site. Synthetic methods and structure-activity relationships are discussed.

  DOI：

  10.1021/jm00217a014
• 作为产物：
  描述：

  3,3-双甲基磺酰基-1-苯丙酮 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以78%的产率得到3-苯基-5-甲硫基异恶唑
  参考文献：
  名称：

  Regioselective Synthesis of 5-Alkylthio- and 3-Alkylthioisoxazoles from Acylketene Dithioacetals

  摘要：

  从酰基乙烯二硫代乙醛 2 发展出了异构的 5-烷硫基和 3-烷硫基异噁唑 3 和 4 的区域选择性合成方法。因此，在甲醇回流中，在甲醇钠存在下，2a-l 与盐酸羟胺反应，可以得到 3-取代的 5-烷基硫代异噁唑 3a-l，收率很高。当化合物 2a-l 与盐酸羟胺在乙酸钠/乙酸（pH 2.2）存在下于回流乙醇/苯中反应时，3-烷基硫代异噁唑 4a-l 以良好的产率被选择性地得到。本文讨论了 3 和 4 的质谱碎片和形成机理。

  DOI：

  10.1055/s-1989-27133

文献信息

• Studies on heterocyclic chemistry—V
  作者：T. Nishiwaki、T. Kitamura、A. Nakano

  DOI：10.1016/s0040-4020(01)97842-1

  日期：1970.1

  It has been revealed that 1-azirines having an ester function at C can be synthesized by the thermally induced skeletal rearrangement of 5-alkoxyisoxazoles and 5-alkylmercaptoisoxazles. Characterization of the azirines obtained was made by chemical reactions as well as by spectrometry. A further thermal transformation of azirine esters into oxazole derivatives could not be found. Mass spectra of representative

  已经发现，可以通过热诱导5-烷氧基异恶唑和5-烷基巯基异恶唑的骨架重排来合成在C具有酯官能的1-叠氮基。通过化学反应以及光谱法对获得的叠氮基进行表征。找不到将叠氮基酯进一步热转化为恶唑衍生物。借助分辨率质谱法对代表性的1-azirines的质谱进行了讨论，其在电子轰击下的行为与它们的化合价异构体5-烷氧基异恶唑的行为相关。
• PURKAYASTHA, M. L.;ILA, H.;JUNJAPPA, H., SYNTHESIS,(1989) N, C. 20-24
  作者：PURKAYASTHA, M. L.、ILA, H.、JUNJAPPA, H.

  DOI：——

  日期：——
• CARR J. B.; DURHAM H. G.; HASS D. K., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 7, 934-939
  作者：CARR J. B.、 DURHAM H. G.、 HASS D. K.

  DOI：——

  日期：——
• Isoxazole anthelmintics
  作者：John B. Carr、Harry G. Durham、D. Kendall Hass

  DOI：10.1021/jm00217a014

  日期：1977.7

  A series of 3-halo-5-phenyl- and 3-phenyl-5-haloisoxazoles has demonstrated anthelmintic activity at doses ranging from 16 to 500 mg/kg orally against the rat roundworm, Nippostrongylus braziliensis. In the 5-phenyl series a halogen at the 3 position of the isoxazole ring was required for activity. However, in the 3-phenyl series activity was maintained after replacement of the 5-halogen with certain alkoxyl, thioalkoxyl, or amino groups. The 3-phenyl and 5-phenyl series apparently are not acting biologically at a common receptor site. Synthetic methods and structure-activity relationships are discussed.
• Regioselective Synthesis of 5-Alkylthio- and 3-Alkylthioisoxazoles from Acylketene Dithioacetals
  作者：M. L. Purkayastha、H. Ila、H. Junjappa

  DOI：10.1055/s-1989-27133

  日期：——

  A regioselective synthesis of isomeric 5-alkylthio- and 3-alkylthioisoxazoles 3 and 4 has been developed from acylketene dithioacetals 2. Thus the reaction of 2a-l with hydroxylamine hydrochloride in the presence of sodium methoxide in refluxing methanol afforded 3-substituted 5-alkylthioisoxazoles 3a-l in good yields. When compounds 2a-l were reacted with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene, 3-alkylthioisoxazoles 4a-l were obtained regioselectively in good yields. Mass-spectral fragmentation and the mechanism of the formation of 3 and 4 are discussed.

  从酰基乙烯二硫代乙醛 2 发展出了异构的 5-烷硫基和 3-烷硫基异噁唑 3 和 4 的区域选择性合成方法。因此，在甲醇回流中，在甲醇钠存在下，2a-l 与盐酸羟胺反应，可以得到 3-取代的 5-烷基硫代异噁唑 3a-l，收率很高。当化合物 2a-l 与盐酸羟胺在乙酸钠/乙酸（pH 2.2）存在下于回流乙醇/苯中反应时，3-烷基硫代异噁唑 4a-l 以良好的产率被选择性地得到。本文讨论了 3 和 4 的质谱碎片和形成机理。

表征谱图