N,5-二苯基-1,2,4-恶二唑-3-胺 | 58599-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N,5-二苯基-1,2,4-恶二唑-3-胺
• 英文名称: N,5-diphenyl-1,2,4-oxadiazol-3-amine
• 英文别名: phenyl-(5-phenyl-[1,2,4]oxadiazol-3-yl)-amine；phenyl-(phenyl-[1,2,4]oxadiazol-3-yl)-amine；Phenyl-(phenyl-[1,2,4]oxadiazol-3-yl)-amin；3-Phenylamino-5-phenyl-1,2,4-oxadiazol
• CAS: 58599-06-7
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: PLTGELJFWNLSBC-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C(Solv: ethanol (64-17-5))
• 沸点：
  395.9±25.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,5-二苯基-1,2,4-恶二唑-3-胺 以10%的产率得到
  参考文献：
  名称：

  BUSCEMI, SILVESTRC;CICERO, MARIA G.;VIVONA, NICOLO;CARONNA, TULLIO, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 931-935

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯酰基-3-苯基硫脲 在 羟胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N,5-二苯基-1,2,4-恶二唑-3-胺
  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

• Facile synthesis of 3-amino-5-aryl-1,2,4-oxadiazoles via PIDA-mediated intramolecular oxidative cyclization
  作者：Kuan Lu、Liancheng Duan、Boxuan Xu、Weile Yin、Di Wu、Yanfang Zhao、Ping Gong

  DOI：10.1039/c6ra08871f

  日期：——

  A mild and efficient method for the synthesis of 3-amino-5-aryl-1,2,4-oxadiazole by intramolecular cyclization using PhI(OAc)2 (PIDA) as an oxidant is developed. Various 3-amino-5-aryl-1,2,4-oxadiazoles are prepared in moderate to good yields, and the PIDA-mediated N–O bond formation mechanism is suggested. In view of the readily available starting materials, operational simplicity, high functionality

  开发了一种温和有效的方法，以PhI（OAc）2（PIDA）为氧化剂，通过分子内环化合成3-氨基-5-芳基-1,2,4-恶二唑。以中等到良好的产率制备了各种3-氨基-5-芳基-1,2,4-恶二唑，并提出了由PIDA介导的N–O键形成机理。鉴于容易获得的起始原料，操作简便，高功能耐受性和低毒性，该方案为1,2,4-恶二唑提供了一种新颖的合成策略。
• (3+2) Annulation of Amidinothioureas with Binucleophile: Synthesis and Antimicrobial Activity of 3-Phenylamino-5-aryl/alkyl-1,2,4-oxadiazole Derivatives
  作者：Swapnil G. Yerande、Amruta B. Ghaisas、Kiran M. Newase、Wei Wang、Kan Wang、Alexander Dömling

  DOI：10.1002/jhet.1873

  日期：2014.11

  efficient method for preparation of 3‐phenylamino‐5‐aryl/alkyl‐1,2,4‐oxadiazole by (3+2) annulation of amidinothioureas with binucleophilic hydroxylamine hydrochloride in the presence of mercury (II) chloride. Desired 3‐phenylamino‐5‐aryl/alkyl‐1,2,4‐oxadiazole was prepared in good to moderate yields. On the basis of the literature precedence, the mechanism for the formation of 3‐phenylamino‐5‐aryl/alkyl‐1

  在本文中，我们报告了在氯化汞（II）存在下，通过（3 + 2）氨基硫脲与双亲核羟胺盐酸盐环化（3 + 2）制备3-苯基氨基-5-芳基/烷基1,2,4-恶二唑的有效方法。所需的3-苯基氨基-5-芳基/烷基1,2,4-恶二唑的制备得率中等至中等。根据文献的优先次序，提出了3-苯基氨基-5-芳基/烷基1,2,4-恶二唑的形成机理。测试了合成的化合物的抗菌活性，并显示出对革兰氏阳性细菌（金黄色葡萄球菌）和真菌（白色念珠菌）的抑制作用。
• Goetz,N.; Zeeh,B., Synthesis, 1976, p. 268 - 270
  作者：Goetz,N.、Zeeh,B.

  DOI：——

  日期：——
• A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine
  作者：Kamala Vasu、Hitesh Jalani、V. Sudarsanam

  DOI：10.1055/s-0032-1317504

  日期：——

  An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exotrig cyclization.
• Buscemi, Silvestre; Cicero, Maria G.; Vivona, Nicolo, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 931 - 935
  作者：Buscemi, Silvestre、Cicero, Maria G.、Vivona, Nicolo、Caronna, Tullio

  DOI：——

  日期：——