2-(methylthio)-5-phenyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(methylthio)-5-phenyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine
• 英文别名: 2-(Methylsulfanyl)-5-phenyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine；2-methylsulfanyl-5-phenyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine
• 化学式: C₁₃H₉F₃N₄S
• mdl: MFCD04050137
• 分子量: 310.302
• InChiKey: OKGNUWGOCBGENV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(methylthio)-5-phenyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine 在 sodium tungstate (VI) dihydrate 、 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 C₁₃H₉F₃N₄O₂S
  参考文献：
  名称：

  Triazolopyrimidines as a New Herbicidal Lead for Combating Weed Resistance Associated with Acetohydroxyacid Synthase Mutation

  摘要：

  Acetohydroxyacid synthase (AHAS; also known as acetolactate synthase; EC 2.2.1.6, formerly EC 4.1.3.18) is the first common enzyme in the biosynthetic pathway leading to the branched-chain amino acids in plants and a wide range of microorganisms. Weed resistance to AHAS-inhibiting herbicides, increasing at an exponential rate, is becoming a global problem and leading to an urgent demand of developing novel compounds against both resistant and wild AHAS. In the present work, a series of novel 2-aroxyl-1,2,4-triazolopyrimidine derivatives (a total of 55) were designed and synthesized with the aim to discover an antiresistant lead compound. Fortunately, the screening results indicated that many of the newly synthesized compounds showed a better, even excellent, inhibition effect against both the wild-type Arabidopsis thaliana AHAS and P197L mutants. Among them, compounds 5-3 to 5-17, compounds 5-19 to 5-26, compounds 5-28 to 5-45, and compound 5-48 have the lower values of resistance factor (RF) and display a potential power to overcome resistance associated with the P197L mutation in the enzyme levels. Further greenhouse in vivo assay showed that compounds 5-15 and 5-20 displayed "moderate" to "good" herbicidal activity against both the wild type-and the resistant (P197L mutation) Descurainia sophia, even at a rate as low as 0.9375 (g of ai/ha). The above results indicated that these two compounds could be used as new leads for the future development of antiresistance herbicides.

  DOI：

  10.1021/acs.jafc.6b00720
• 作为产物：
  描述：

  3-氨基-5-甲硫基-1H-1,2,4-三唑 、 lithium;(Z)-1,1,1-trifluoro-4-oxo-4-phenylbut-2-en-2-olate 在 溶剂黄146 作用下， 反应 168.0h， 以65%的产率得到2-(methylthio)-5-phenyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  摘要：

  Cyclocondensation of fluorine-containing lithium beta-diketonates with 3-amino-1,2,4-triazoles afforded 7-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidines.

  DOI：

  10.1023/a:1024777828344