5,7-di-tert-butyl-2-(p-tolyl)benzo[d]oxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,7-di-tert-butyl-2-(p-tolyl)benzo[d]oxazole
• 英文别名: 5,7-Di-tert-butyl-2-(4-methyl-phenyl)-benzooxazole；5,7-ditert-butyl-2-(4-methylphenyl)-1,3-benzoxazole
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: NBSBJBTYUDHYNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-4,6-二(2-甲基-2-丙基)苯酚 在 lead dioxide 、 溶剂黄146 作用下， 反应 3.0h， 生成 5,7-di-tert-butyl-2-(p-tolyl)benzo[d]oxazole
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of new 2-substituted 5,7-di-tert-butylbenzoxazoles

  摘要：

  Various synthetic pathways of the 30 novel 2-substituted 5,7-di-tert-butylbenzoxazoles as new potential antimicrobial drugs are discussed. The 28 intermediates are described as well. The compounds were characterized by H-1 and C-13 NMR spectra, MS spectra, IR/UV spectra and by means of CHN analysis. The purity of the final compounds was checked by HPLC and their lipophilicity (log K) was also determined by means of RP-HPLC. In the present study, the correlation between RP-HPLC retention parameter log K (the logarithm of capacity factor K) and various calculated log P data is shown. The target compounds were tested for their in vitro antimycobacterial activity. Several compounds showed antituberculotic activity comparable with or higher than the standard isoniazide. In vitro cytotoxicity testing of the most active benzoxazoles and isoniazide as a reference drug was performed using MTT assay and compared with isoniazide as a reference drug. Structure-activity relationships among the chemical structures, the physical properties and the biological activities of the evaluated compounds are discussed in the article. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.030

文献信息

• Metal‐Free Oxidative Condensation of Catechols, Aldehydes and NH ₄ OAc towards Benzoxazoles
  作者：Shaofeng Wu、Dan Zhou、Furong Geng、Jianyu Dong、Lebin Su、Yongbo Zhou、Shuang‐Feng Yin

  DOI：10.1002/adsc.202100249

  日期：——

  facile and green synthesis of such valuable compounds from easily available substrates will make a contribution to drug, material, and fine chemistry. A method for the synthesis of benzoxazoles from catechols, aldehydes and ammonium acetate is developed using NaIO4 as oxidant under metal- and additive-free conditions. A broad range of benzoxazoles including some fluorescent whitening agents, JTP-426467

  苯并恶唑广泛存在于生物活性化合物、天然产物、药物和功能材料中。因此，从容易获得的底物轻松和绿色合成这些有价值的化合物将为药物、材料和精细化学做出贡献。开发了一种在无金属和无添加剂条件下使用 NaIO 4作为氧化剂从儿茶酚、醛和醋酸铵合成苯并恶唑的方法。广泛的苯并恶唑，包括一些荧光增白剂、JTP-426467 和 tafamidis 类似物，以 56-95% 的产率合成，具有出色的官能团耐受性。机械研究表明，一个有趣的o-亚氨基环己二烯醇中间体参与反应。该协议的这些显着特点使其成为苯并恶唑合成的替代方案。
• METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND
  申请人：THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY

  公开号：US20170066711A1

  公开（公告）日：2017-03-09

  A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:

  提供一种从含有所述芳香C—O键的羟基芳烃制备具有芳香C—N键正交于芳香C—O键的芳烃的方法。该方法包括以下步骤：a) 对羟基芳烃进行正交氧化以产生一个正交醌，b) 将正交醌与氮亲核试剂缩合以生成化合物IVa或IVb的化合物，c) 允许化合物IVa或IVb发生1,5-氢原子转移，从而分别产生具有化合物Va和Vb的C—O键正交的C—N键的芳烃。
• Consecutive Oxidation/Condensation/Cyclization/Aromatization Sequences Catalyzed by Nanostructured Iron(III)‐Porphyrin Complex towards Benzoxazole Derivatives
  作者：Jasem Aboonajmi、Hashem Sharghi、Mahdi Aberi、Pezhman Shiri

  DOI：10.1002/ejoc.202000999

  日期：2020.10.8

  Divers benzoxazole heterocyclic products have been synthesized by a facile, efficient, and eco‐friendly strategy. The synthesis of benzoxazoles was catalyzed by nanostructured iron(III)‐porphyrin complex at room temperature under green conditions.

  Divers苯并恶唑杂环产品是通过一种简便，高效且环保的策略合成的。纳米结构的铁（III）-卟啉配合物在室温和绿色条件下催化合成苯并恶唑。
• One-Pot Multicomponent Reaction of Catechols, Ammonium Acetate, and Aldehydes for the Synthesis of Benzoxazole Derivatives Using the Fe(III)–Salen Complex
  作者：Hashem Sharghi、Jasem Aboonajmi、Mahdi Aberi

  DOI：10.1021/acs.joc.0c00560

  日期：2020.5.15

  The Fe(III)-salen complex has been applied successfully as a catalyst for the novel, simple, efficient, and one-pot multicomponent synthesis of benzoxazole derivatives from catechols, ammonium acetate as the nitrogen source, and aldehydes (nontoxic and cheap alternatives of amines) for the first time. Using this procedure, a wide range of benzoxazoles was successfully synthesized in the presence of

  Fe（III）-salen配合物已成功地用作催化剂，用于新型，简单，高效，一锅多酚合成邻苯二酚，乙酸铵作为氮源和乙醛的苯并恶唑衍生物（无毒和廉价的替代品）胺）。使用该程序，在温和的条件下，在EtOH中，在催化剂存在下，成功合成了多种苯并恶唑，所有产物均以优异的收率获得。据我们所知，该方法是使用这些起始原料进行多组分合成苯并恶唑衍生物的第一个实例。显着的特征，例如使用被认为是良性氧化剂的空气和使用EtOH作为绿色溶剂，易于产品分离，易于获得且廉价的醛，和温和的条件使我们的程序对于有机合成更加有效和实用。此外，当前协议已成功地应用于大规模合成期望的产品。
• An efficient electrochemical method for the atom economical synthesis of some benzoxazole derivatives
  作者：Hamid Salehzadeh、Davood Nematollahi、Hooman Hesari

  DOI：10.1039/c3gc40954f

  日期：——

  Electrochemical synthesis of some 2-arylbenzoxazoles were directly carried out via the electrochemical oxidation of 3,5-di-tert-butylcatechol in the presence of benzylamines without using any catalyst under mild and green conditions. The results show that electrogenerated 3,5-di-tert-butyl-1,2-benzoquinone participates in the reaction with benzylamine derivatives and, via the ECCE mechanism “electron

  一些2- arylbenzoxazoles的电化学合成方法直接进行经由的电化学氧化3,5-二叔丁基邻苯二酚 在不使用任何苄胺的情况下 催化剂在温和的绿色条件下。结果表明，电致3,5-二-叔丁基-1,2-苯醌参与与苄胺衍生物和该反应中，通过将ECCE机制“电子转移 +化学反应（亚胺 形成）+化学反应（环化）+ 电子转移”，转换为相应的 苯并恶唑衍生品。在这项工作中，一些苯并恶唑 水溶液中高收率的衍生物，无毒试剂和 溶剂 提供了一种使用环保的新颖方法的碳电极的制造方法。