5,7-di-tert-butyl-2-(m-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-(m-tolyl)benzo[d]oxazole
• 英文别名: 5,7-Di-tert-butyl-2-(3-methyl-phenyl)-benzooxazole；5,7-ditert-butyl-2-(3-methylphenyl)-1,3-benzoxazole
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: GEQZPIDMAVCPCC-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-(m-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

• 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。
• [3+1+1] Annulation Reaction of Benzo‐1,2‐Quinones, Aldehydes and Hydroxylamine Hydrochloride: Access to Benzoxazoles with Inorganic Nitrogen Source
  作者：Fulin Chen、Chuanle Zhu、Huanfeng Jiang

  DOI：10.1002/adsc.202001521

  日期：2021.4.13

  By employing large‐tonnage industrial feedstock inorganic hydroxylamine hydrochloride as the nitrogen source, its [3+1+1] annulation reaction with benzo‐1,2‐quinones and aldehydes delivers various useful benzoxazoles in high yields. Preliminary mechanistic studies prove that the quinone oxime rather than the aldehyde oxime is the reaction intermediate.

  报道了用无机氮源合成苯并恶唑。通过使用大吨位工业原料无机盐胺盐酸盐作为氮源，其与苯并1,2-醌和醛的[3 + 1 + 1]环化反应可高产率提供各种有用的苯并恶唑。初步的机理研究证明，醌肟而不是醛肟是反应的中间体。
• Application of <i>Vitreoscilla</i> Hemoglobin as a Green and Efficient Biocatalyst for the Synthesis of Benzoxazoles in Water
  作者：Yaning Xu、Nan Zhao、Fengxi Li、Chunyu Wang、Hanqing Xie、Junhao Wu、Lei Cheng、Lei Wang、Zhi Wang

  DOI：10.1002/cbic.202300609

  日期：2024.1.2

  We report an efficient and eco‐friendly method for the Vitreoscilla hemoglobin (VHb)‐catalyzed synthesis of benzoxazoles in water at room temperature. tert‐Butyl hydroperoxide and 2,2,6,6‐tetramethyl‐1‐piperidinyloxy were used as oxidant and radical scavenger, respectively. A total of 27 functionally diverse benzoxazoles were prepared in moderate to high yields (62 %‐94 %) by the annulation reaction of phenols with amines in the presence of VHb in 1 h. Thus, this method is highly viable for practical applications. This work broadens the application of hemoglobin to organic synthesis.

  摘要 我们报告了一种室温下在水中由葡萄孢血红蛋白（VHb）催化合成苯并恶唑的高效且环保的方法。叔丁基过氧化氢和2,2,6,6-四甲基-1-哌啶基氧基分别用作氧化剂和自由基清除剂。在 VHb 存在下，苯酚与胺在 1 小时内发生环化反应，共制备出 27 种不同功能的苯并恶唑，收率从中等到较高不等 (62 %-94 %)。因此，这种方法在实际应用中非常可行。这项工作拓宽了血红蛋白在有机合成中的应用。
• Synthesis and antimicrobial evaluation of new 2-substituted 5,7-di-tert-butylbenzoxazoles
  作者：Jarmila Vinsova、Katerina Cermakova、Alexandra Tomeckova、Martina Ceckova、Josef Jampilek、Pavel Cermak、Jiri Kunes、Martin Dolezal、Frantisek Staud

  DOI：10.1016/j.bmc.2006.05.030

  日期：2006.9

  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.