3-Piperidino-5-phenyl-1,2,4-oxadiazol | 58476-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Piperidino-5-phenyl-1,2,4-oxadiazol
• 英文别名: 5-Piperidino-3-phenyl-oxadiazol-(1,2,4)；5-phenyl-3-(1-piperidyl)-1,2,4-oxadiazole；1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-piperidine；1-(5-Phenyl-1,2,4-oxadiazol-3-yl)piperidine；5-phenyl-3-piperidin-1-yl-1,2,4-oxadiazole
• CAS: 58476-83-8
• 化学式: C₁₃H₁₅N₃O
• 分子量: 229.282
• InChiKey: BMQJBPQMVQXZHA-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  371.5±25.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Benzamide, N-(1-piperidinylthioxomethyl)- 在 羟胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3-Piperidino-5-phenyl-1,2,4-oxadiazol
  参考文献：
  名称：

  Facile synthesis of 3-aryl/alkylamino 5-aryl/alkyl 1,2,4-oxadiazoles from acylthiourea

  摘要：

  Facile and selective synthesis of 3-aryl/alkylamino 5-aryl/alkyl 1,2,4-oxadiazoles starting from N-acylthioureas has been demonstrated. The regio-selectivity is achieved by simply selecting an appropriate base used for the generation of hydroxyl amine from the corresponding hydrochloride salt. This method also avoids the use of toxic cyanogen bromide. The structure of the synthesized oxadiazoles has been resolved by tandem mass spectral studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.048

文献信息

• Synthèse d'amino-oxadiazoles - 1, 2, 4
  作者：F. Eloy、R. Lenaers

  DOI：10.1002/hlca.19660490428

  日期：——

  Two new syntheses of 5-amino-1,2,4-oxadiazoles are described. The first one is based on the reaction of guanidine on benzhydroxamyl chloride. The second is more general and consists in allowing primary or secondary amines, hydrazine or guanidine to react with 5-trichloromethyloxadiazoles.

  描述了5-氨基-1，2，4-恶二唑的两种新的合成。第一个是基于胍与苯并氧杂戊酰氯的反应。第二个更普遍，在于使伯胺或仲胺，肼或胍与5-三氯甲基恶二唑反应。
• <i>N</i>-Halogen Compounds of Cyanamide Derivatives. VIII. A Convenient Method of Preparing 1,2,4-Oxadiazoles from<i>N</i>-Haloamidino Compounds
  作者：Toshio Fuchigami、Keijiro Odo

  DOI：10.1246/bcsj.49.3607

  日期：1976.12

  A new, efficient method for the preparation of 1,2,4-oxadiazoles from N-benzoylamidino compounds by treatment with t-butyl hypochlorite and sodium hydroxide has been devised. It was supposed that the ring formation proceeds via a nitrene intermediate.

  设计了一种新的、有效的方法，通过用次氯酸叔丁酯和氢氧化钠处理，从 N-苯甲酰脒基化合物制备 1,2,4-恶二唑。据推测，环的形成是通过氮烯中间体进行的。
• Buscemi, Silvestre; Frenna, Vincenzo; Caronna, Tullio, Heterocycles, 1992, vol. 34, # 12, p. 2313 - 2322
  作者：Buscemi, Silvestre、Frenna, Vincenzo、Caronna, Tullio、Vivona, Nicolo

  DOI：——

  日期：——
• Facile synthesis of 3-aryl/alkylamino 5-aryl/alkyl 1,2,4-oxadiazoles from acylthiourea
  作者：Gundala Chennakrishnareddy、Hazra Debasis、Rapai Jayan、Sulur G. Manjunatha

  DOI：10.1016/j.tetlet.2011.09.048

  日期：2011.11

  Facile and selective synthesis of 3-aryl/alkylamino 5-aryl/alkyl 1,2,4-oxadiazoles starting from N-acylthioureas has been demonstrated. The regio-selectivity is achieved by simply selecting an appropriate base used for the generation of hydroxyl amine from the corresponding hydrochloride salt. This method also avoids the use of toxic cyanogen bromide. The structure of the synthesized oxadiazoles has been resolved by tandem mass spectral studies. (C) 2011 Elsevier Ltd. All rights reserved.