2-[4-(嘧啶-2-基)哌嗪-1-基]-1,3-苯并恶唑 | 1015727-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-[4-(嘧啶-2-基)哌嗪-1-基]-1,3-苯并恶唑
• 英文名称: 2-(4-(pyrimidin-2-yl)piperazin-1-yl)benzo[d]oxazole
• 英文别名: 2-(4-Pyrimidin-2-ylpiperazin-1-yl)-1,3-benzoxazole
• CAS: 1015727-57-7
• 化学式: C₁₅H₁₅N₅O
• 分子量: 281.317
• InChiKey: QAZUNHZIXOFVAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-巯基苯并恶唑 在 五氯化磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 2-[4-(嘧啶-2-基)哌嗪-1-基]-1,3-苯并恶唑
  参考文献：
  名称：

  作为有效抗癌剂的2-取代-1,3-苯并恶唑和3-[（（3-取代）丙基] -1,3-苯并恶唑-2（3 H）-one衍生物的合成和初步评价

  摘要：

  描述了一系列新的含苯并恶唑和苯并恶唑酮衍生物的环胺的合成和细胞毒性活性。2-环胺-1,3-苯并恶唑5a - k，5-氯-3-（3-氯丙基）-1,3-苯并恶唑-2（3 H）-一8和3- [3-（环氨基） ]丙基] -1,3-苯并恶唑-2（3 H）-ones 9a – f被合成。已经对在苯并恶唑支架中环胺部分的存在影响的新合成的化合物对四种人类癌细胞系的细胞毒性作用进行了评估。对新化合物进行了评估，以查看苯并恶唑基序第二和第三位置的取代是否影响它们对癌细胞的细胞毒性作用。

  DOI：

  10.1007/s00044-010-9353-y

文献信息

• Copper-Catalyzed Electrophilic Amination of Benzoxazoles via Magnesation
  作者：Sangback Lee、Yunmi Lee

  DOI：10.1002/ejoc.201900335

  日期：2019.5.26

  A mild and efficient method for the synthesis of 2‐aminobenzoxazoles through a Cu‐catalyzed electrophilic amination of benzoxazole derivatives with O‐benzoyl hydroxylamines by direct magnesation has been developed.

  已经开发了一种温和有效的方法，该方法通过直接氧化反应，通过邻苯二甲酰基衍生物与邻苯二甲酰基羟胺的铜催化亲电胺化反应合成2-氨基苯并恶唑。
• Preparation of derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents
  作者：Irwin Becker

  DOI：10.1002/jhet.5570450410

  日期：2008.7

  This paper describes the preparation of twenty-eight derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents. In twenty-six of the preparations a chloro nitrogen heterocycle was caused to react with an excess of 1-(2-pyrimidinyl)piperazine in the absence of solvent. A specific example is given above.

  本文介绍了1-（2-嘧啶基）哌嗪28种衍生物的制备，它们可作为潜在的抗焦虑药，抗抑郁药和抗精神病药。在不存在溶剂的情况下，在26种制剂中，使氯氮杂环与过量的1-（2-嘧啶基）哌嗪反应。上面给出了一个具体的例子。
• Efficient and Novel Synthesis of Benzoxazole Derivatives in the Presence of Zinc Dust Under Solvent-Free Conditions
  作者：M. S. R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav

  DOI：10.1080/00397910903320621

  日期：2010.8.31

  A mild and efficient method has been developed for the synthesis of 2-cyclic amine-substituted benzoxazole derivatives using zinc dust under microwave irradiation in the absence of solvent is described. A comparative study was performed under conventional and microwave heating conditions. Zinc dust can be reused several times after reactivation. The significant feature of this method is the isolation

  描述了一种温和有效的方法，用于在没有溶剂的情况下在微波辐射下使用锌粉合成 2-环胺取代的苯并恶唑衍生物。在常规和微波加热条件下进行了比较研究。锌粉在重新激活后可以重复使用多次。该方法的显着特点是在较短的反应时间内通过简单的后处理分离出高纯度的纯产品。
• Metal free amination of 2-chloroazoles in aqueous medium
  作者：R. Uday Kumar、K. Harsha Vardhan Reddy、B.S.P. Anil Kumar、G. Satish、V. Prakash Reddy、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2015.12.084

  日期：2016.2

  A green approach for the synthesis of 2-amino azoles by the reaction of 2-chloro azoles with various types of amines using water as an environment friendly solvent at room temperature has been developed. The significant features of this methodology are short reaction time and easy product separation. This approach provides various biologically active compounds in good to excellent yields without adding any catalyst, ligand, or base. (C) 2015 Elsevier Ltd. All rights reserved.
• CsF–Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)-benzoxazolone derivatives
  作者：M. S. R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav、U. S. N. Murty、K. Pranay Kumar

  DOI：10.1007/s00044-010-9367-5

  日期：2011.6

  The synthesis and antimicrobial activity studies of a new series of cyclic amine containing benzoxazoles and benzoxazolone-2(3H)-ones derivatives were described. The alkylation of benzoxazolone was carried out using cesium fluoride-Celite. The newly synthesized compounds with the influence of the induction of the cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to the antibacterial and antifungal activity. The 2-cyclic amine-1,3-benzoxazoles (5a-l), 5-chloro-3-alkyl substituted-1,3-benzoxazol-2(3H)-ones (8a-f), and 3-[3-(cyclic amine)propyl]-1,3-benzoxazol-2(3H)-ones (9a-f) were synthesized. These derivatives were tested for antibacterial and antifungal activity. Among the compounds tested, 8c and 9f showed moderate to good antibacterial and antifungal activity. Compound 8a showed good antifungal activity.