N-(2-methylphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine | 117080-50-9

• 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: N-(2-methylphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine
• 英文别名: 2-(2-methylphenyl)amino-5-(4-pyridyl)-1,3,4-oxadiazole；N-(2-methylphenyl)-5-(4-pyridinyl)-1,3,4-oxadiazol-2-amine；N-(2-methylphenyl)-5-pyridin-4-yl-1,3,4-oxadiazol-2-amine
• CAS: 117080-50-9
• 化学式: C₁₄H₁₂N₄O
• 分子量: 252.275
• InChiKey: BWTXZVKZZUJDCU-UHFFFAOYSA-N

物化性质

• 熔点：
  276-278 °C(Solv: ligroine (8032-32-4); ethyl ether (60-29-7))
• 沸点：
  432.3±55.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-甲基苯基)-3-(吡啶-4-羰基氨基)硫脲 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以92%的产率得到N-(2-methylphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  Electrochemically initiated oxidative cyclization: a versatile route for the synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles

  摘要：

  A rapid, improved, and environmentally benign synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles by one-pot electrocyclization of acylthiosemicarbazones is reported. Controlled potential electrolysis was performed at room temperature in acetonitrile as non-aqueous solvent and LiClO4 as supporting electrolyte. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetric data. Better yields at room temperature, shortest reaction time, and easy work-up are attractive features of this green procedure.

  DOI：

  10.1007/s00706-011-0711-3

文献信息

• Synthesis of 2-amino-1,3,4-oxadiazoles from isoselenocyanates via cyclodeselenization
  作者：Yuanyuan Xie、Junli Liu、Ping Yang、Xiangjun Shi、Jianjun Li

  DOI：10.1016/j.tet.2011.05.100

  日期：2011.7

  An efficient one-pot method to access 2-amino-1,3,4-oxadiazoles from isoselenocyanates and hydrazides or dihydrazides was developed via cyclodeselenization. Without any harsh reagents, various 2-amino-1,3,4-oxadiazoles were obtained in considerably high yields (82%-97%) and purities (>99%) directly with simple crystallization in ethanol. And the formed precipitated Se powder during the reaction could be recycled for preparation of isoselenocyanates efficiently. A plausible mechanism is proposed for the formation of the target products. (C) 2011 Elsevier Ltd. All rights reserved.
• Yar, Mohammad Shahar; Akhter, Mohammad Wasim, Acta poloniae pharmaceutica, 2009, vol. 66, # 4, p. 393 - 397
  作者：Yar, Mohammad Shahar、Akhter, Mohammad Wasim

  DOI：——

  日期：——
• ZHANG, ZIYI;YANG, KEXIN;ZENG, FULI, CHEM. J. CHIN. UNIV., 9,(1988) N 3, 239-245
  作者：ZHANG, ZIYI、YANG, KEXIN、ZENG, FULI

  DOI：——

  日期：——
• Electrochemically initiated oxidative cyclization: a versatile route for the synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles
  作者：Sushma Singh、Laxmi Kant Sharma、Apoorv Saraswat、R. K. P. Singh

  DOI：10.1007/s00706-011-0711-3

  日期：2012.10

  A rapid, improved, and environmentally benign synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles by one-pot electrocyclization of acylthiosemicarbazones is reported. Controlled potential electrolysis was performed at room temperature in acetonitrile as non-aqueous solvent and LiClO4 as supporting electrolyte. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetric data. Better yields at room temperature, shortest reaction time, and easy work-up are attractive features of this green procedure.