2-methylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole | 23767-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
• 英文别名: 2-methylsulfanyl-5-(3,4,5-trimethoxy-phenyl)-[1,3,4]oxadiazole；5-(3,4,5-Trimethoxy-phenyl)-2-methylmercapto-1,3,4-oxadiazol；2-Methylsulfanyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
• CAS: 23767-44-4
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: MRSFNZMGMZNRDL-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143 °C(Solv: ethanol (64-17-5))
• 沸点：
  427.9±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 在 ammonium heptamolybdate 、 [bmim]PF₆ 、 双氧水 作用下， 反应 2.0h， 以89%的产率得到2-methanesulfonyl-5-(3,4,5-trimethoxy-phenyl)-[1,3,4]oxadiazole
  参考文献：
  名称：

  Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives

  摘要：

  Starting from the key intermediate 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole-2-thiol (4) or the oxadiazole analogue (5), the title compounds 9 and 10 are synthesized by a two-step process. Thioetherification reaction of 4 or 5 with an organic halide catalyzed by indium or indium tribromide first affords appropriate sulfide 7 or 8, which is then converted into title compounds 9 or 10 by hydrogen peroxide oxidation catalyzed by ammonium molybdate in ionic liquid [bmim]PF6. The structures are unequivocally confirmed by spectroscopic (IR, H-1 and C-13 NMR) data and elemental analyses. The structures of 8d and 10q are further established by X-ray crystallographic diffraction analysis. The compounds have been shown to be fungicidally active. Title compounds 10i and 10j can inhibit mycelia growth by approximately 50% (EC50) at 2.9-93.3 mu g/mL in vitro against 10 kinds of fungi. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.014
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰肼 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 2-methylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure–anti-mycobacterial activities

  摘要：

  The preparation of novel 5-aryt-2-thio-1,3,4-oxadiazoles 4a 41 and the computer-aided study of their in vitro anti-tubercular activity against Myeobacterium tuberculosis H(37)Rv (ATCC 27294) are reported. The average accuracy of the electronic-topological method and neural network methods applied to the activity prediction in leave-one-out cross validation is 80%. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.011

文献信息

• Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure–anti-mycobacterial activities
  作者：Fliur Macaev、Ghenadie Rusu、Serghei Pogrebnoi、Alexandru Gudima、Eugenia Stingaci、Ludmila Vlad、Nathaly Shvets、Fatma Kandemirli、Anatholy Dimoglo、Robert Reynolds

  DOI：10.1016/j.bmc.2005.05.011

  日期：2005.8

  The preparation of novel 5-aryt-2-thio-1,3,4-oxadiazoles 4a 41 and the computer-aided study of their in vitro anti-tubercular activity against Myeobacterium tuberculosis H(37)Rv (ATCC 27294) are reported. The average accuracy of the electronic-topological method and neural network methods applied to the activity prediction in leave-one-out cross validation is 80%. (c) 2005 Elsevier Ltd. All rights reserved.
• Mazzone; Bonina; Arrigo Reina, Farmaco, Edizione Scientifica, 1977, vol. 32, # 6, p. 414 - 429
  作者：Mazzone、Bonina、Arrigo Reina

  DOI：——

  日期：——
• Madhavan,R.; Srinivasan,V.R., Indian Journal of Chemistry, 1969, vol. 7, p. 760 - 765
  作者：Madhavan,R.、Srinivasan,V.R.

  DOI：——

  日期：——
• Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives
  作者：Cai-Jun Chen、Bao-An Song、Song Yang、Guang-Fang Xu、Pinaki S. Bhadury、Lin-Hong Jin、De-Yu Hu、Qian-Zhu Li、Fang Liu、Wei Xue、Ping Lu、Zhuo Chen

  DOI：10.1016/j.bmc.2007.04.014

  日期：2007.6

  Starting from the key intermediate 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole-2-thiol (4) or the oxadiazole analogue (5), the title compounds 9 and 10 are synthesized by a two-step process. Thioetherification reaction of 4 or 5 with an organic halide catalyzed by indium or indium tribromide first affords appropriate sulfide 7 or 8, which is then converted into title compounds 9 or 10 by hydrogen peroxide oxidation catalyzed by ammonium molybdate in ionic liquid [bmim]PF6. The structures are unequivocally confirmed by spectroscopic (IR, H-1 and C-13 NMR) data and elemental analyses. The structures of 8d and 10q are further established by X-ray crystallographic diffraction analysis. The compounds have been shown to be fungicidally active. Title compounds 10i and 10j can inhibit mycelia growth by approximately 50% (EC50) at 2.9-93.3 mu g/mL in vitro against 10 kinds of fungi. (C) 2007 Elsevier Ltd. All rights reserved.