2-(allylsulfanyl)-5-methyl-1,3,4-thiadiazole | 88276-00-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(allylsulfanyl)-5-methyl-1,3,4-thiadiazole
• 英文别名: 1,3,4-Thiadiazole, 2-methyl-5-(2-propenylthio)-；2-methyl-5-prop-2-enylsulfanyl-1,3,4-thiadiazole
• CAS: 88276-00-0
• 化学式: C₆H₈N₂S₂
• mdl: MFCD06020581
• 分子量: 172.275
• InChiKey: IXWWVUDSJRLGQE-UHFFFAOYSA-N

物化性质

• 沸点：
  269.2±33.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(allylsulfanyl)-5-methyl-1,3,4-thiadiazole 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以97%的产率得到3-allyl-5-methyl-1,3,4-thiadiazole-2(3H)-thione
  参考文献：
  名称：

  Halocyclization of S- and N-alkenyl derivatives of 5-methyl-1,3,4-thiadiazole-2-thione

  摘要：

  2-Allylsulfanyl-5-methyl-1,3,4-thiadiazole, 2-(2-bromoallylsulfanyl)-5-methyl-1,3,4-thiadiazole, 2-[(but-3-en-1-yl)sulfanyl]-5-methyl-1,3,4thiadiazole, and 2-methyl-5-[(pent-4-en-1-yl)sulfanyl]-1,3,4-thiadiazole were obtained by alkylation of 5-methyl-1,3,4-thiadiazole-2-thione. Halocyclization of the obtained unsaturated sulfides produced derivatives of thiazolo[2,3-b][1,3,4] thiadiazolium, 6,7-dihydro-5H-[1,3,4]thiadiazolo[2,3-b][1,3]thiazinium, and 5,6,7,8-tetrahydro[1,3,4]thiadiazolo[2,3-b][1,3]thiazepinium systems.

  DOI：

  10.1007/s10593-015-1797-z
• 作为产物：
  描述：

  3-溴丙烯 、 2-巯基-5-甲基-1,3,4-噻二唑 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以43.7%的产率得到2-(allylsulfanyl)-5-methyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Design and development of 1,3,4-thiadiazole based potent new nano-fungicides

  摘要：

  Being the important organic reaction intermediates and biological scaffolds, a series of 2-alkyl/aralkyl/ heterocyclyl sulfanyl-5-amino/methyl-1,3,4-thiadiazoles have been synthesized by suitable synthetic route and characterized by analytical and spectral data. The evaluation of these compounds for their bioefficacy against two phyto-pathogenic fungi revealed their fungicidal potency against Rhizoctonia bataticola (ED50 values, 3.9-300.4 mu g/mL) and Rhizoctonia solani (ED50 values, 4.2-228.5 mu g/mL). To further augment their fungicidal efficacy, the potent five fungicidal compounds were nano-sized. The protocol for preparing 1,3,4-thiadiazole based nano-fungicide employing polyethylene glycol was developed and standardized. Characterization of nano-forms of 1,3,4-thiadiazole derivatives by particle size analyzer and electron microscopy (TEM) techniques confirmed the <100 nm average particle sizes of all nano-fungicides. The 2-4 times higher fungicidal activity was observed with nano-forms than the corresponding conventional sized 1,3,4-thiadiazole derivatives against phytopathogenic fungi, namely, Rhizoctonia solani and R. bataticola. (C) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2020.128507

文献信息

• Preparation of thioethers
  申请人：Gist-Brocades N.V.

  公开号：US04496720A1

  公开（公告）日：1985-01-29

  A novel process for the preparation of thioethers comprising reacting a silylated thiol of the formula R--S--SiR.sub.1 R.sub.2 R.sub.3 I wherein R is an organic group and R.sub.1, R.sub.2 and R.sub.3 are individually selected from the group consisting of alkyl of 1 to 4 carbon atoms with an organic halide, sulfate or sulfonate in the presence of hexamethylphosphoric triamide as a solvent or co-solvent preferably under neutral conditions in aprotic solvents at a temperature between 0.degree. and 150.degree. C.

  一种新型的制备硫醚的方法，包括将具有化学式R--S--SiR.sub.1 R.sub.2 R.sub.3 I的硅烷基硫醇与有机卤化物、硫酸酯或磺酸酯在六甲基膦酸三胺存在下反应，其中R为有机基，R.sub.1、R.sub.2和R.sub.3分别选自1至4个碳原子的烷基，最好在无极性溶剂中在0度至150度之间的中性条件下进行。
• Process for the preparation of thioethers
  申请人：GIST-BROCADES N.V.

  公开号：EP0088831A1

  公开（公告）日：1983-09-21

  Process for the preparation of thioethers by reacting a silylated thiol of the general formula: wherein R represents an organic group and R1, R2 and R3 are the same or different and each represents an alkyl group having 1 to 4 carbon atoms, with an organic halide, sulphate or sulphonate in the presence of hexamethylphosphoric triamide as a solvent or co-solvent. The process is carried out under neutral conditions in aprotic solvents at a temperature between 0° and 150°C.

  通式为：其中 R 代表有机基团，R1、R2 和 R3 相同或不同，且各自代表具有 1 至 4 个碳原子的烷基的硅烷化硫醇与有机卤化物、硫酸盐或磺酸盐在作为溶剂或助溶剂的六甲基磷酸三酰胺存在下反应制备硫醚的工艺。 该工艺在中性条件下，在温度为 0° 至 150°C 的钝溶剂中进行。
• US4233216A
  申请人：——

  公开号：US4233216A

  公开（公告）日：1980-11-11
• US4496720A
  申请人：——

  公开号：US4496720A

  公开（公告）日：1985-01-29
• Design and development of 1,3,4-thiadiazole based potent new nano-fungicides
  作者：Suprabhat Pal、Vikrant Singh、Rajesh Kumar、Robin Gogoi

  DOI：10.1016/j.molstruc.2020.128507

  日期：2020.11

  Being the important organic reaction intermediates and biological scaffolds, a series of 2-alkyl/aralkyl/ heterocyclyl sulfanyl-5-amino/methyl-1,3,4-thiadiazoles have been synthesized by suitable synthetic route and characterized by analytical and spectral data. The evaluation of these compounds for their bioefficacy against two phyto-pathogenic fungi revealed their fungicidal potency against Rhizoctonia bataticola (ED50 values, 3.9-300.4 mu g/mL) and Rhizoctonia solani (ED50 values, 4.2-228.5 mu g/mL). To further augment their fungicidal efficacy, the potent five fungicidal compounds were nano-sized. The protocol for preparing 1,3,4-thiadiazole based nano-fungicide employing polyethylene glycol was developed and standardized. Characterization of nano-forms of 1,3,4-thiadiazole derivatives by particle size analyzer and electron microscopy (TEM) techniques confirmed the <100 nm average particle sizes of all nano-fungicides. The 2-4 times higher fungicidal activity was observed with nano-forms than the corresponding conventional sized 1,3,4-thiadiazole derivatives against phytopathogenic fungi, namely, Rhizoctonia solani and R. bataticola. (C) 2020 Elsevier B.V. All rights reserved.