5-(4-methoxyphenyl)-3-(methylthio)isoxazole | 120803-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxyphenyl)-3-(methylthio)isoxazole
• 英文别名: 3-methylthio-5-(4-methoxyphenyl)-isoxazole；5-(4-Methoxyphenyl)-3-methylsulfanyl-1,2-oxazole
• CAS: 120803-17-0
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: QNTLKNZLJJWBGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  S-methyl 3-oxo-3-(4-methoxylphenyl)propanedithioate 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 9.0h， 以72%的产率得到5-(4-methoxyphenyl)-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。
• Tetrahydroisoquinoline derived PRMT5-inhibitors
  申请人：CTXT PTY LTD

  公开号：US10647708B2

  公开（公告）日：2020-05-12

  A compound of formula (I) wherein: R1 is optionally one or more halo or methyl groups; R2a and R2b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R2c and R2d are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R3a and R3b are independently selected from H and Me; R4 is either H or Me; R5 is either H or Me; A is either (i) optionally substituted phenyl; (ii) optionally substituted naphthyl; or (iii) optionally substituted C5-12 heteroaryl.

  式(I)化合物 其中R1 任选为一个或多个卤代或甲基； R2a 和 R2b 独立选自以下组： (i) F；(ii) H；(iii) Me；和 (iv) CH2OH； R2c 和 R2d 独立选自以下组(R3a 和 R3b 独立选自 H 和 Me；R4 是 H 或 Me；R5 是 H 或 Me；A 是 (i) 任选取代的苯基；(ii) 任选取代的萘基；或 (iii) 任选取代的 C5-12 杂芳基。
• 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：——
• TETRAHYDROISOQUINOLINE DERIVED PRMT5-INHIBITORS
  申请人：CTXT PTY LTD

  公开号：US20170283407A1

  公开（公告）日：2017-10-05

  A compound of formula (I) wherein: R 1 is optionally one or more halo or methyl groups; R 2a and R 2b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH 2 OH; R 2c and R 2d are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH 2 OH; R 3a and R 3b are independently selected from H and Me; R 4 is either H or Me; R 5 is either H or Me; A is either (i) optionally substituted phenyl; (ii) optionally substituted naphthyl; or (iii) optionally substituted C 5-12 heteroaryl.
• 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.

表征谱图