1-methyl-3,5-bis(trifluoromethyl)-1,2,4-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-3,5-bis(trifluoromethyl)-1,2,4-triazole
• 英文别名: 3,5-bis(trifluoromethyl)-1-methyl-1H-1,2,4-triazole；1-methyl-3,5-bis(trifluoromethyl)-1H-12,4-triazole
• 化学式: C₅H₃F₆N₃
• 分子量: 219.089
• InChiKey: MNMNKSSKKZSJAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,5-双(三氟甲基)-4-甲基-4H-1,2,4-三唑 反应 2.0h， 以58%的产率得到1-methyl-3,5-bis(trifluoromethyl)-1,2,4-triazole
  参考文献：
  名称：

  Perfluoro-1,3,4-oxadiazoles

  摘要：

  Some new polyfluorinated 1,3,4-oxadiazoles have been obtained via a two-step method. The cycloadditions of the 1,3,4-oxadiazoles have been studied and an analysis of the energies of the frontier orbitals calculated by the MNDO method indicates a LUMO-dependent pathway for cycloaddition.

  DOI：

  10.1016/s0022-1139(00)80860-x

文献信息

• Unsaturated nitrogen compounds containing fluorine. Part 16. The synthesis of 3,5-bis(trifluoromethyl)-1H-1,2,4-triazole and some 4-substituted derivatives from 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene
  作者：Mohamad M. Abdul-Ghani、Anthony E. Tipping

  DOI：10.1016/0022-1139(94)03199-a

  日期：1995.5

  The dichloroazine 5 has been converted into the monoaminoazines CF3C(NHR)=NN=CClCF3 (6) [a, R = Ph (89%); b, R = H (81%); c, R = Me (89%); d, R = CH2CO2Me (96%); e, R = CH2CO2Et (95%)] and the diaminoazines CF3C(NHR) = NN = C(NHR)CF3 (4) [c, R = H (96%); d, R = Me (94%); e, R = CH2CO2Me (50%); f, R = CH2CO2Et (77%)] by reaction with ammonia or the appropriate primary amino compound; with hydroxylamine

  二氯嗪5已经转化为单氨基嗪CF 3 C（NHR）＝ NN ＝ CClCF 3（6）[a，R ＝ Ph（89％）； n ＝ 1。b，R ＝ H（81％）；c，R = Me（89％）；d，R ＝ CH 2 CO 2 Me（96％）；e，R ＝ CH 2 CO 2 Et（95％）]和二氨基嗪CF 3 C（NHR）＝ NN ＝ C（NHR）CF 3（4）[c，R ＝ H（96％）；e，R ＝H（96％）。d，R ＝ Me（94％）；e，R ＝ CH 2 CO 2 Me（50％）；f，R = CH 2 CO 2 Et（77％）]与氨或适当的伯氨基化合物反应；与羟胺的合成-肟CF 3 CCl = NNHC（CF 3）=生成NOH（8）（86％）。混合的二氨基嗪CF 3 C（NHR）= NN = C（NHR'）CF 3（4）[g，R = H，R'= Ph; h，R'= Me，R'= H；i，R ＝ Me，R′＝
• Unsaturated nitrogen compounds containing fluorine. Part 17. The reactions of 3,5-bis(trifluoromethyl)-1H-1,2,4-triazole with alkynes, alkenes and diazomethane, and of sodium 3,5-bis(trifluoromethyl)-1,2,4-triazolide with halogen compounds
  作者：Mohamad M. Abdul-Ghani、Anthony E. Tipping

  DOI：10.1016/0022-1139(94)03181-x

  日期：1995.5

  (81%) and the exo-norborn-5-ene 18 (92%), respectively, while reaction with diazomethane (12) gave the 1-methyl-1H-1,2,4-triazole (19) (92%). Treatment of triazole 1 with an equivalent amount of sodium hydride in solvent (Et2O, MeCN or THF) afforded the corresponding sodium triazolide (6), which on reaction in situ with halogen compounds gave the following products: EtO2CCH2Br (29) (in Et2O/EtOH) → RCH2CO2Et

  3,5-双（三氟甲基）-1的热反应ħ -1,2,4-三唑（1）与炔烃HC≡CCO 2的Et（7）（120℃）中，Me-O 2 CC≡CCO 2 Me（8）（120°C）和Me 3 SiC≡CSiMe 3（9）（150°C）得到以下产物，其中R = C = NC（CF3）=N⎴N-：7 →（E）-RCH = CHCO 2 Et（13a）（46％）+（Z）-RCH = CHCO 2 Et（13b）（49％）; 8→（E）-或（Z）-MeO 2 CCR = CHCO 2 Me（14）（82％）; 9 →（E）-RCH = CHSiMe 3（15）（37％）+（Z）-Me 3 SiCR = CHSiMe 3（16b）（22％）。前两种反应涉及在炔烃的亲核攻击由三唑1，而后者反应可能参与的炔protodesilyiation 9，得到HC≡CSiMe 3（23）和电加成三唑1至两个炔9和23电加成三唑1至烯烃CH