5,7-di-tert-butyl-2-phenylbenzo[d]oxazole | 117077-85-7

• 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-phenylbenzo[d]oxazole
• 英文别名: 5,7-di-tert-butyl-2-phenylbenzoxazole；5,7-Di-tert-butyl-2-phenyl-benzooxazole；5,7-ditert-butyl-2-phenyl-1,3-benzoxazole
• CAS: 117077-85-7
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: DFPYVAVDBULFBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,7-di-tert-butyl-2-phenylbenzo[d]oxazole 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以64%的产率得到5-(tert-butyl)-2-phenylbenzoxazole
  参考文献：
  名称：

  METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND

  摘要：

  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。

  公开号：

  US20170066711A1
• 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-phenylbenzo[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。
• OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature
  作者：Xu Meng、Yanmin Wang、Yuanguang Wang、Baohua Chen、Zhenqiang Jing、Gexin Chen、Peiqing Zhao

  DOI：10.1021/acs.joc.7b01119

  日期：2017.7.7

  sensitive groups (hydroxyl, cyano, amino, vinyl, ethynyl, ester, and even acetyl groups) and heterocycles, which affords functionalized benzoxazoles in good to excellent yields by employing low catalyst loading (2 mol % Cu). The characterization and plausible catalytic mechanism of Cu(OH)x/OMS-2 are described. The notable features of our catalytic protocol such as the use of air as the benign oxidant

  在氧化锰八面体分子筛（OMS-2）负载的氢氧化铜Cu（OH）x / OMS-2的存在下，在室温下通过多米诺氧化/环化从邻苯二酚和胺类中好氧合成苯并恶唑。通过在Cu（OH）x / OMS-2上有效氧化邻苯二酚引发的这种异质苯并恶唑合成可以耐受多种底物，尤其是含有敏感基团（羟基，氰基，氨基，乙烯基，乙炔基，酯，甚至乙酰基）的胺以及杂环，通过使用低催化剂负载量（2摩尔％的铜），可以提供优良至极佳收率的官能化苯并恶唑。Cu（OH）x的表征和可能的催化机理描述了/ OMS-2。我们催化方案的显着特征，例如使用空气作为良性氧化剂，使用EtOH作为溶剂，条件温和，易于产品分离，可扩展至克级，并且催化剂具有出色的可重复使用性（最多10个循环）使它对于有机合成更加实用且对环境友好。
• 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。
• Amino Acids: Nontoxic and Cheap Alternatives for Amines for the Synthesis of Benzoxazoles through the Oxidative Functionalization of Catechols
  作者：Hashem Sharghi、Jasem Aboonajmi、Mahdi Aberi、Mohsen Shekouhy

  DOI：10.1002/adsc.201901096

  日期：2020.3.4

  was applied for the synthesis of benzoxazoles via a C(aryl)−OH functionalization of catechol derivatives and amines in ethanol at room temperature. In the next step, amino acids have been applied as nontoxic and cheap alternatives for amines. The obtained products were similar with the regular amines case. This is the first report about the application of amino acids as alternatives for primary amines

  纳米磁性的Fe 3 ö 4（NM-的Fe 3 ö 4）施加用于苯并恶唑的合成通过一个C（芳基）-OH在室温下在乙醇儿茶酚衍生物和胺的官能化。在下一步中，氨基酸已被用作胺的无毒且廉价的替代品。所得产物与常规胺的情况相似。这是关于氨基酸在有机合成中作为伯胺替代品的应用的第一份报告。此外，所提出的方法已成功地用于大规模合成所需产物。
• Reactions of<i>O</i>-methyl<i>o</i>-quinone monoximes with methyl-, methylene- and methine- substituted aromatic compounds. Synthesis of benzo[<i>d</i>]oxazole and 1,4-benzoxazine derivatives
  作者：Demetrios N. Nicolaides、R. Wajih Awad、Georgios K. Papageorgiou、Efthalia Kojanni、Constantinos A. Tsoleridis

  DOI：10.1002/jhet.5570340602

  日期：1997.11

  O-Methyl o-quinone monoxime 1 reacts thermally with compounds 2a-d or 6a,b or 7a,b to give mainly the corresponding 2-substituted phenanthroxazoles 3a-c and 8. The reaction of 1 with aromatic methylene compounds lOa-c affords the ketones 13a-c in moderate to high yields. Similar products are also obtained from the reaction of monoximes 15a,b with some of the above reactants. The unexpected products

  ø -甲基ø -quinone肟1发生反应热用化合物2A-d或6A，6B或图7A，B主要得到相应的2-取代的phenanthroxazoles 3A-C和8。1与芳族亚甲基化合物10a-c的反应以中等至高收率得到酮13a-c。从一恶魔15a，b与一些上述反应物的反应中也获得了类似的产物。的意想不到的产品5和20从反应得到的1与2-甲基咪唑（2D）和苯基环氧乙烷（19），而4 H -1,4-恶嗪衍生物23是由1与茚（21）的反应获得的。