3-methylthieno<3,2-c>isoxazole | 57892-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methylthieno<3,2-c>isoxazole
• 英文别名: 3-Methyl-thieno<3,2-c>isoxazol；3-methylthieno[3,2-c]isoxazole；3-Methylthieno[3,2-c][1,2]oxazole；3-methylthieno[3,2-c][1,2]oxazole
• CAS: 57892-93-0
• 化学式: C₆H₅NOS
• 分子量: 139.178
• InChiKey: MLPHNGJHOXOOLK-UHFFFAOYSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  239.1±20.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methylthieno<3,2-c>isoxazole 以5%的产率得到4,5-dihydrothieno[3,2-b]pyrrol-6-one
  参考文献：
  名称：

  Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene

  摘要：

  Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azido[1]benzothiophene at 300 degrees C provides 3-methyl[1]benzothieno[3,2-c]isoxazole (72%). At higher temperatures, the heteroindoxyl 1,2-dihydro[1]benzothieno[3,2-b]pyrrol-3-one was obtained in low yield (ca. 10%). The heteroindoxyl exists as a mixture of keto and enol forms in DMSO solution. Because of the easy oxidative dimerisation of these products to indigotin (and its heteroanalogues), such reactions are excellent examples of the synthetic advantages of FVP with the monomeric products conveniently generated under vacuum in a solvent-free, air-free environment.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p011.239
• 作为产物：
  描述：

  以95%的产率得到3-methylthieno<3,2-c>isoxazole
  参考文献：
  名称：

  Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene

  摘要：

  Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azido[1]benzothiophene at 300 degrees C provides 3-methyl[1]benzothieno[3,2-c]isoxazole (72%). At higher temperatures, the heteroindoxyl 1,2-dihydro[1]benzothieno[3,2-b]pyrrol-3-one was obtained in low yield (ca. 10%). The heteroindoxyl exists as a mixture of keto and enol forms in DMSO solution. Because of the easy oxidative dimerisation of these products to indigotin (and its heteroanalogues), such reactions are excellent examples of the synthetic advantages of FVP with the monomeric products conveniently generated under vacuum in a solvent-free, air-free environment.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p011.239

文献信息

• Synthesis and Chemistry of 4,5-Dihydrothieno[3,2-<i>b</i>]pyrrol-6-one—A Heteroindoxyl
  作者：Alexander P. Gaywood、Hamish McNab

  DOI：10.1021/jo900496u

  日期：2009.6.5

  by nitrous acid, and provides an N-methylene Meldrum’s acid derivative on treatment with methoxymethylene Meldrum’s acid. Reactions of 4,5-dihydrothieno[3,2-b]pyrrol-6-one with diazonium salts, with isatin, and with dimethyl acetylenedicarboxylate take place at the methylene position to provide a hydrazone, an indirubin analogue, and a succinate derivative, respectively. Oxidation of 4,5-dihydrothieno[3

  2-乙酰基-3-叠氮基噻吩的快速真空热解（FVP）在炉温为350°C时产生3-甲基噻吩并[3,2- c ]异恶唑为主要产物，而在高于550°C的温度下产生了新的杂吲哚基4，仅形成5-二氢噻吩并[3，2- b ]吡咯-6-。杂吲哚基主要作为酮互变异构体存在。据O-由TFA质子化，N-乙酰化由乙酸酐，Ñ -nitrosated由亚硝酸，并提供了一个Ñ与甲氧基亚甲基Meldrum酸处理亚甲基Meldrum酸衍生物。4,5-二氢噻吩并[3,2- b]的反应具有重氮盐，靛红和乙炔二羧酸二甲酯的] pyrrol-6-one在亚甲基位置发生，分别提供，靛玉红类似物和琥珀酸酯衍生物。4,5-二氢噻吩并[3,2- b ]吡咯-6-的氧化产生异靛青素，相对于靛蓝素本身，其在紫外光谱中显示出变色现象。
• Dyall, Leonard K.; Suffolk, Peter M.; Dehaen, Wim, Journal of the Chemical Society. Perkin transactions II, 1994, # 10, p. 2115 - 2119
  作者：Dyall, Leonard K.、Suffolk, Peter M.、Dehaen, Wim、L'abbe, Gerrit

  DOI：——

  日期：——
• Paulmier,C., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1975, vol. 281, p. 317 - 319
  作者：Paulmier,C.

  DOI：——

  日期：——
• Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene
  作者：Alexander P. Gaywood、Hamish McNab、Lilian McNab

  DOI：10.24820/ark.5550190.p011.239

  日期：——

  Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azido[1]benzothiophene at 300 degrees C provides 3-methyl[1]benzothieno[3,2-c]isoxazole (72%). At higher temperatures, the heteroindoxyl 1,2-dihydro[1]benzothieno[3,2-b]pyrrol-3-one was obtained in low yield (ca. 10%). The heteroindoxyl exists as a mixture of keto and enol forms in DMSO solution. Because of the easy oxidative dimerisation of these products to indigotin (and its heteroanalogues), such reactions are excellent examples of the synthetic advantages of FVP with the monomeric products conveniently generated under vacuum in a solvent-free, air-free environment.[GRAPHICS].