2-(4-benzylpiperazin-1-yl)benzoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(4-benzylpiperazin-1-yl)benzoxazole
• 英文别名: 2-(4-benzylpiperazin-1-yl)benzo[d]oxazole；2-(4-benzylpiperazin-1-yl)-1,3-benzoxazole；2-(4-Benzyl-piperazin-1-yl)-benzooxazole
• 化学式: C₁₈H₁₉N₃O
• 分子量: 293.368
• InChiKey: YAORDQFXLRHICI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.277
• 拓扑面积：
  32.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(((4-benzylpiperazin-1-yl)methylene)amino)phenol 在 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到2-(4-benzylpiperazin-1-yl)benzoxazole
  参考文献：
  名称：

  高价碘试剂的无金属合成2-氨基苯并恶唑

  摘要：

  通过开环和随后的闭环方法，通过苯并恶唑与胺的CH键胺化反应，已经开发出一种简便，简单，温和且无金属的2-氨基苯并恶唑合成方法。反应分两个步骤进行，其中在无溶剂或无溶剂条件下，在不存在任何试剂或催化剂的情况下，通过苯并恶唑进行胺的亲核加成，然后使用2-碘氧基苯甲酸作为高价碘试剂进行氧化闭环。在优化的反应条件下，各种环状，无环和官能化的脂肪族胺均具有良好的耐受性，并且各自的2-氨基苯并恶唑的收率良好至极佳。

  DOI：

  10.1016/j.tetlet.2012.12.127

文献信息

• Synthesis and preliminary evaluation of 2-substituted-1,3-benzoxazole and 3-[(3-substituted)propyl]-1,3-benzoxazol-2(3H)-one derivatives as potent anticancer agents
  作者：M. S. R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav、Janapala Venkateswara Rao、Vino T. Cheriyan、Ruby John Anto

  DOI：10.1007/s00044-010-9353-y

  日期：2011.6

  The synthesis and cytotoxic activity studies of a new series of cyclic amine containing benzoxazole and benzoxazolone derivatives are described. The 2-cyclic amine-1,3-benzoxazoles 5a–k, 5-chloro-3-(3-chloropropyl)-1,3-benzoxazol-2(3H)-one 8 and 3-[3-(cyclic amino)propyl]-1,3-benzoxazol-2(3H)-ones 9a–f were synthesized. The newly synthesized compounds with the influence of the presence of cyclic amine

  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。
• Metal-free N-iodosuccinimide-catalyzed mild oxidative C–H bond amination of benzoxazoles
  作者：Yogesh S. Wagh、Dinesh N. Sawant、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2012.04.117

  日期：2012.7

  facile, efficient, and mild protocol for the synthesis of aminobenzoxazoles has been developed using direct oxidative C–H bond amination of benzoxazoles with secondary or primary amines. The reaction was performed using catalytic amount of N-iodosuccinimide and aqueous hydrogen peroxide as a green oxidant and in the absence of transition metals. Reaction proceeds smoothly at ambient temperature and

  通过使用仲胺或伯胺对苯并恶唑进行直接氧化C–H键胺化反应，已开发出一种简便，高效且温和的氨基苯并恶唑合成方法。使用催化量的N-碘琥珀酰亚胺和过氧化氢水溶液作为绿色氧化剂并在没有过渡金属的情况下进行反应。反应在环境温度下平稳进行，并且需要较短的反应时间以提供所需产物的优异产率。在优化的反应条件下，各种环状，无环和官能化的脂肪族胺均具有良好的耐受性，并且各自氨基苯并恶唑的收率良好至极佳。
• 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。
• Synthesis of 2-Piperazinylbenzothiazole and 2-Piperazinylbenzoxazole Derivatives with 5-HT3 Antagonist and 5-HT4 Agonist Properties
  作者：Antonio Monge、Maria del Carmen Pena、Juan Antonio Palop、Jose Maria Caldero、Juan Roca、Elisa Garcia、Gonzalo Romero、Joaquin del Rio、Berta Lasheras

  DOI：10.1021/jm00035a012

  日期：1994.4

  New 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives were prepared and tested as 5-HT3 receptor antagonists. Some of the new compounds antagonized the effect of 5-HT at the longitudinal muscle myenteric plexus (LMMP) preparation of the guinea pig ileum, and two benzothiazole derivatives, compounds 2e and 2f, were more potent than ondansetron in this regard. However, these two compounds were much weaker than the typical 5-HT3 receptor antagonist as displacers of [H-3]BRL-43694 binding to rat cerebral cortex homogenates or as antagonists of the bradycardia response to 5-HT in the anaesthetized rat. Like the prokinetic agent cisapride, some of the new compounds enhanced gastric emptying in rats. Compound 2f not only markedly enhanced gastric emptying but was also a potent agonist at the isolated rat oesophageal tunics muscularis mucosae, a preparation sensitive to 5-HT4 receptor stimulation, and enhanced the twitch response in the LMMP preparation. The latter effect was blocked by a high concentration of tropisetron or by previous desensitization with 6-methoxytryptamine Compound 2f appears to show a promising pharmacological profile as a potential gastrokinetic agent.
• 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.