2-[(ethoxycarbonyl)methylthio]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole | 67572-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(ethoxycarbonyl)methylthio]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
• 英文别名: ethyl 2-(5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)acetate；[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-acetic acid ethyl ester；2-Mercapto-<5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazolyl>-essigsaeureethylester；Ethyl 2-[[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetate
• CAS: 67572-44-5
• 化学式: C₁₅H₁₈N₂O₆S
• mdl: MFCD01859209
• 分子量: 354.384
• InChiKey: LINLQDZQRPQVBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C(Solv: ethanol (64-17-5))
• 沸点：
  488.2±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  52.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[(ethoxycarbonyl)methylthio]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以45.3%的产率得到Ethyl 2-[[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfinyl]acetate
  参考文献：
  名称：

  Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.02.006
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰肼 在 氢氧化钾 、 sodium hydroxide 、 indium(III) bromide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-[(ethoxycarbonyl)methylthio]-5-(3,4,5-trimethoxyphenyl)-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

文献信息

• Mazzone; Bonina, Farmaco, Edizione Scientifica, 1978, vol. 33, # 6, p. 438 - 452
  作者：Mazzone、Bonina

  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.
• 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.