5-(furan-2-yl)-3-(methylthio)isoxazole | 120803-23-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(furan-2-yl)-3-(methylthio)isoxazole
• 英文别名: 3-methylthio-5-(2-furyl)-isoxazole；5-(Furan-2-yl)-3-methylsulfanyl-1,2-oxazole
• CAS: 120803-23-8
• 化学式: C₈H₇NO₂S
• 分子量: 181.215
• InChiKey: RVAQKHRKGPLZEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 3-(furan-2-yl)-3-oxopropanedithioate 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以78%的产率得到5-(furan-2-yl)-3-(methylthio)isoxazole
  参考文献：
  名称：

  Divergent Reactivity in the Reaction of β-Oxodithioesters and Hydroxylamine: Access to β-Ketonitriles and Isoxazoles

  摘要：

  Starting from beta-oxodithioesters and hydroxylamine, two completely different transformations afford either beta-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of beta-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave beta-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of beta-oxodithioesters and hydroxylamine in HOAc at 90 degrees C.

  DOI：

  10.1021/acs.joc.5b01869

文献信息

• 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。
• 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：——
• Divergent Reactivity in the Reaction of β-Oxodithioesters and Hydroxylamine: Access to β-Ketonitriles and Isoxazoles
  作者：Jiaheng Li、Wei Ma、Wenbo Ming、Cong Xu、Na Wei、Mang Wang

  DOI：10.1021/acs.joc.5b01869

  日期：2015.11.6

  Starting from beta-oxodithioesters and hydroxylamine, two completely different transformations afford either beta-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of beta-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave beta-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of beta-oxodithioesters and hydroxylamine in HOAc at 90 degrees C.