5-trichloromethyl-2-methyl-3-phenyl-2,3-dihydro-1,2,4-oxadiazole | 121994-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-trichloromethyl-2-methyl-3-phenyl-2,3-dihydro-1,2,4-oxadiazole
• 英文别名: 2-methyl-3-phenyl-5-(trichloromethyl)-3H-1,2,4-oxadiazole
• CAS: 121994-37-4
• 化学式: C₁₀H₉Cl₃N₂O
• 分子量: 279.553
• InChiKey: IYYDABVSHNECFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(benzylidene)methylamine N-oxide 、 三氯乙腈 反应 0.05h， 以82%的产率得到5-trichloromethyl-2-methyl-3-phenyl-2,3-dihydro-1,2,4-oxadiazole
  参考文献：
  名称：

  1,3-Dipolar Cycloaddition of Nitriles under Microwave Irradiation in Solvent-Free Conditions

  摘要：

  Several nitriles were allowed to react with nitrones or nitrile oxides in the absence of solvent under microwave irradiation within 2-10 min to give 2,3-dihydro-1,2,4-oxadiazoles or 1,2,4-oxadiazoles, respectively.

  DOI：

  10.3987/com-96-7412

文献信息

• 1,3-Dipolar cycloaddition of nitrones with nitriles.
  作者：Pedro H.H. Hermkens、Jan H.v. Maarseveen、Chris G. Kruse、Hans W. Scheeren

  DOI：10.1016/s0040-4020(01)89838-0

  日期：——

  nitriles 14–16, proceeded under thermal as well as under high pressure conditions with complete regioselectivity to give Δ4-1,2,4-oxadiazolines 17–19. In general, the cycloaddition seemed to be controlled by a HOMO(nitrone)- LUMO(nitrile) interaction. However, a crossover in the orbital control is probable observed with nitrile 16c. Nitrone-nitrile cycloadditions are normal type II cycloadditions so that

  硝酮的1,3-偶极环加成1-6与腈14-16，下热以及与完整区域选择性高的压力条件下进行，得到Δ 4 -1,2,4-恶二唑啉17-19。通常，环加成似乎受HOMO（硝酮）-LUMO（腈）相互作用控制。但是，用腈16c可能会在轨道控制中发生交叉现象。腈-腈环加成是正常的II型环加成，因此腈具有U形反应性曲线。溶剂极性和Hammett方程的动力学研究表明，从机理上讲，腈-腈环加成与硝基-烯烃环加成是一致的。
• 1,3-Dipolar Cycloaddition of Nitriles under Microwave Irradiation in Solvent-Free Conditions
  作者：Angel Díaz-Ortiz、Enrique Díez-Barra、Antonio de la Hoz、Andrés Moreno、Maria J. Gómez-Escalonilla、André Loupy

  DOI：10.3987/com-96-7412

  日期：——

  Several nitriles were allowed to react with nitrones or nitrile oxides in the absence of solvent under microwave irradiation within 2-10 min to give 2,3-dihydro-1,2,4-oxadiazoles or 1,2,4-oxadiazoles, respectively.