2-benzylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole | 892440-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-benzylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole
• 英文别名: 2-Benzylsulfanyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole；2-benzylsulfanyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole
• CAS: 892440-82-3
• 化学式: C₁₈H₁₈N₂O₃S₂
• 分子量: 374.485
• InChiKey: TVUHNNYGMKTWOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-benzylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole 在 ammonium heptamolybdate 、 [bmim]PF₆ 、 双氧水 作用下， 反应 2.0h， 以93%的产率得到2-Benzylsulfonyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole
  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：

  5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole-2-thiol 、 alkaline earth salt of/the/ methylsulfuric acid 在 indium 、 sodium hydroxide 作用下， 反应 4.0h， 以96%的产率得到2-benzylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole
  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

文献信息

• 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.
• Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety
  作者：Fang Liu、Xiao-Qiong Luo、Bao-An Song、Pinaki S. Bhadury、Song Yang、Lin-Hong Jin、Wei Xue、De-Yu Hu

  DOI：10.1016/j.bmc.2008.02.006

  日期：2008.4.1

  Selective oxidation of sulfides 7 or 8 to sulfoxides 9 or 10 is achieved by mCPBA. The structures of the compounds 9 or 10 are confirmed by elemental analysis, IR, and H-1 NMR. The bioassay results showed that title compound 10a possess high antifungal activities with EC50 values ranging from 19.91 to 63.97 mu g/mL. The mechanism of action of 10a against Sclerotinia sclerotiorum was studied. After treating with compound 10a at 100 mu g/mL for 12 h, the mycelial reducing sugar, D-GlcNAc, soluble protein and pyruvate content, chitinase activity showed declining tendency. (C) 2008 Elsevier Ltd. All rights reserved.