N-(tert-butyl)-3-phenyl-1,2,4-oxadiazol-5-amine | 64734-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(tert-butyl)-3-phenyl-1,2,4-oxadiazol-5-amine
• 英文别名: N-tert-butyl-3-phenyl-1,2,4-oxadiazol-5-amine
• CAS: 64734-30-1
• 化学式: C₁₂H₁₅N₃O
• 分子量: 217.271
• InChiKey: HTHXWYOXPOLCRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-(tert-butyl)-3-phenyl-1,2,4-oxadiazol-5-amine 在 三氟乙酸 作用下， 以 neat (no solvent) 为溶剂， 以82%的产率得到3-苯基-1,2,4-恶二唑-5-胺
  参考文献：
  名称：

  钯通过异氰酸酯插入催化合成5-氨基-1,2,4-恶二唑。

  摘要：

  已经开发了一种方便有效的钯催化方法，用于由a肟和异氰酸酯合成5-氨基1,2,4-恶二唑。在温和条件下以中等至高收率获得了各种5-氨基-1,2,4-恶二唑。该策略成功的关键在于通过钯催化的异氰酸酯插入形成新的C–N键和C–O键。

  DOI：

  10.1039/d0ob01092h
• 作为产物：
  描述：

  5-氯-3-苯基-1,2,4-恶二唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 、 叔丁醇 为溶剂， 生成 N-(tert-butyl)-3-phenyl-1,2,4-oxadiazol-5-amine
  参考文献：
  名称：

  Synthesis of heteroaromatic potential .beta.-adrenergic antagonists by the glycidol route

  摘要：

  The synthesis of several 3-alkylamino-2-hydroxypropyl heteroaryl ethers (13-15, 17, and 18) is described. These compounds were prepared by the alkylamination of the corresponding glycidyl ethers (6-8, 10, and 11), which in turn were obtained from the requisite heteroaryl halides and the sodium salt of glycidol. The above basic ethers exhibited beta-blocking activity, but the potency of the tested compounds was considerably less than that of propanolol. Only 3-tert-butylamino-2-hydroxyl-1-(1,2,4-thiadiazol-5-yl) propyl ether (13) showed some selective myocardial beta-blocking activity.

  DOI：

  10.1021/jm00199a025

文献信息

• Multicomponent Reaction of<i>Z</i>-Chlorooximes, Isocyanides, and Hydroxylamines as Hypernucleophilic Traps. A One-Pot Route to Aminodioximes and Their Transformation into 5-Amino-1,2,4-oxadiazoles by Mitsunobu–Beckmann Rearrangement
  作者：Valentina Mercalli、Alberto Massarotti、Monica Varese、Mariateresa Giustiniano、Fiorella Meneghetti、Ettore Novellino、Gian Cesare Tron

  DOI：10.1021/acs.joc.5b01676

  日期：2015.10.2

  Synthetically useful aminodioximes are prepared via a novel three-component reaction among Z-chlorooximes, isocyanides, and hydroxylamines by exploiting the preferential attack of isocyanides to nitrile N-oxides via a [3 + 1] cycloaddition reaction. The results of quantum mechanical studies of the reaction mechanism are also discussed. Furthermore, the one-pot conversion of aminodioximes to 1,2,3-oxadiazole-5-amines

  可通过Z-氯肟，异氰酸酯和羟胺之间的新型三组分反应制备合成有用的氨基二氧肟，方法是通过[3 +1]环加成反应利用异氰酸酯对腈N-氧化物的优先攻击。还讨论了反应机理的量子力学研究结果。此外，首次报道了通过Mitsunobu-Beckmann重排将氨基二氧肟单锅转化为1,2,3-恶二唑-5-胺。
• Aminonitrones as highly reactive bifunctional synthons. An expedient one-pot route to 5-amino-1,2,4-triazoles and 5-amino-1,2,4-oxadiazoles – potential antimicrobials targeting multi-drug resistant bacteria
  作者：Mikhail V. Il’in、Alexandra A. Sysoeva、Dmitrii S. Bolotin、Alexander S. Novikov、Vitalii V. Suslonov、Elizaveta V. Rogacheva、Liudmila A. Kraeva、Vadim Yu. Kukushkin

  DOI：10.1039/c9nj04529e

  日期：——

  reactive than the N center; it first reacts with in situ generated R2NCBr2 to grant 2-methyl-1,2,4-oxadiazolium salts, which are then converted to the target heterocyclic systems upon treatment with hydrazines or hydroxylamine. The nature and strength of the intramolecular hydrogen bonds N–H⋯N and O–H⋯N, which significantly contribute to the total energies of different transition states and products of

  发达一锅协议到5-氨基-1,2,4-三唑或5-氨基-1,2,4-恶二唑包括相互作用之间aminonitrones - [R 1个C（NH 2）Ñ +（ME）O - （R 1＝ Alk，Ar，Het），异氰酸酯R 2 NC（R 2＝ Alk，Ar），Br 2和肼（对于三唑）或羟胺（对于恶二唑）。这种形式上的四组分反应涉及氨基硝酮，异氰化物，溴和N-亲核试剂，在温和条件下（10分钟，20–25°C）非常迅速地进行，并且对湿气和空气不敏感（在未干燥的CHCl 3中）–MeOH，在空气中），并以良好的收率（最高86％； 26个示例）提供了杂环系统。反应范围包括芳族，杂芳族和脂族氨基硝基，以及脂族和芳族异氰酸酯。DFT计算的结果（理论上为M06-2X / 6-311 + G（d，p）水平）表明，双功能氨基硝基的O-亲核中心比N中心更具反应性；它首先与原位生成的R 2 NCBr 2反应得到2-甲基-1
• ANTONIO Y.; CAMARGO C.; GALEAZZI E.; IRIARTE J.; GUZMAN M.; MUCHOWSKI J. +, J. MED. CHEM. <JMCM-AR>, 1978, 21, NO 1, 123-126
  作者：ANTONIO Y.、 CAMARGO C.、 GALEAZZI E.、 IRIARTE J.、 GUZMAN M.、 MUCHOWSKI J. +

  DOI：——

  日期：——
• Palladium-catalyzed synthesis of 5-amino-1,2,4-oxadiazoles <i>via</i> isocyanide insertion
  作者：Xu Wang、Jin-Ping Fu、Jia-Xing Xie、Qing-Hu Teng、Hai-Tao Tang、Ying-Ming Pan

  DOI：10.1039/d0ob01092h

  日期：——

  palladium-catalyzed approach has been developed for the synthesis of 5-amino-1,2,4-oxadiazoles from amidoximes and isocyanides. Various 5-amino-1,2,4-oxadiazoles were obtained in moderate to high yields under mild conditions. The key to the success of this strategy involves new C–N bond and C–O bond formation via palladium-catalyzed isocyanide insertion.

  已经开发了一种方便有效的钯催化方法，用于由a肟和异氰酸酯合成5-氨基1,2,4-恶二唑。在温和条件下以中等至高收率获得了各种5-氨基-1,2,4-恶二唑。该策略成功的关键在于通过钯催化的异氰酸酯插入形成新的C–N键和C–O键。
• Synthesis of heteroaromatic potential .beta.-adrenergic antagonists by the glycidol route
  作者：Yulia Antonio、Catalina Camargo、Edwige Galeazzi、Jose Iriarte、Margarita Guzman、Joseph M. Muchowski、Kathie Gerrity、Frances Liu、Lois M. Miller、Arthur M. Strosberg

  DOI：10.1021/jm00199a025

  日期：1978.1

  The synthesis of several 3-alkylamino-2-hydroxypropyl heteroaryl ethers (13-15, 17, and 18) is described. These compounds were prepared by the alkylamination of the corresponding glycidyl ethers (6-8, 10, and 11), which in turn were obtained from the requisite heteroaryl halides and the sodium salt of glycidol. The above basic ethers exhibited beta-blocking activity, but the potency of the tested compounds was considerably less than that of propanolol. Only 3-tert-butylamino-2-hydroxyl-1-(1,2,4-thiadiazol-5-yl) propyl ether (13) showed some selective myocardial beta-blocking activity.