(5,7-di-tert-butylbenzo[d]oxazol-2-yl)methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: (5,7-di-tert-butylbenzo[d]oxazol-2-yl)methanol
• 英文别名: 2-hydroxymethyl-4,6-di-tert-butylbenzoxazole；5,7-di-tert-butyl-2-hydroxymethylbenzoxazol；(5,7-Ditert-butyl-1,3-benzoxazol-2-yl)methanol
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: KLDYWWYTCUAAED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 (5,7-di-tert-butylbenzo[d]oxazol-2-yl)methanol 以 乙腈 为溶剂， 生成 Cu(II)(5,7-di-tert-butyl-2-hydroxymethylbenzoxazol)2Cl2
  参考文献：
  名称：

  苯并恶唑基配体与3d金属离子络合的多功能化学转化

  摘要：

  两个苯并恶唑衍生物配位体是从3,5-二-缩合合成叔丁基- ø苯醌（DTBBQ）用在甲醇乙醇胺或1,3-二氨基-2-羟基丙烷。DTBBQ与乙醇胺的缩合得到预期的5,7-二叔丁基-2-亚甲基羟基苯并恶唑（HL1），而与1,3-二氨基-2-羟基丙烷则得到（2-羟乙基-2- {2,4-bis （1,1-二甲基乙基）-1-苯酚-6氨基} -2 {5,7-二叔丁基-苯并恶唑}）（H 2 L2）仅具有一个苯并恶唑环，而不是对称的双-苯并恶唑衍生物。HL1和H 2 L2的结构通过NMR光谱法和X射线衍射在HL1的单晶上证实。HL1与CuCl 2的反应生成了单核[Cu II（HL1）2 Cl 2 ]（1）配合物，其晶体结构表明可以保留HL1。相反，与镍（II），钴（II）和锰（II）反应后，H 2 L2在单核络合物[M II（L3）2 ]中的新配体HL3中进一步被氧化和转化（M = Ni II（2个）; M

  DOI：

  10.1021/ic202493z
• 作为产物：
  描述：

  DL-丝氨酸 、 3,5-二叔丁基邻苯醌 以 乙醇 为溶剂， 反应 5.0h， 以63%的产率得到(5,7-di-tert-butylbenzo[d]oxazol-2-yl)methanol
  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

• 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。
• 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。
• Copper-Catalyzed Aerobic Oxidative C(aryl)OH Bond Functionalization of Catechols with Amines Affording Benzoxazoles
  作者：Xiuling Chen、Fangyan Ji、Yalei Zhao、Yanxi Liu、Yongbo Zhou、Tieqiao Chen、Shuang-Feng Yin

  DOI：10.1002/adsc.201500515

  日期：2015.9.14

  copper‐catalyzed aerobic oxidative C(aryl)OH bond functionalization of catechols is reported. Under air, at room temperature, in the presence of a copper catalyst, catechols react with amines to produce the corresponding benzoxazoles in high yields. Mechanistic studies suggest that the reaction proceeds via an intriguing competitive oxidation and a synergetic catalysis between catechol and amine.

  据报道，第一个铜催化的邻苯二酚的好氧氧化C（芳基）OH键功能化。在空气中，在室温下，在铜催化剂的存在下，儿茶酚与胺反应生成高产率的相应苯并恶唑。机理研究表明，该反应通过有趣的竞争性氧化和邻苯二酚与胺之间的协同催化而进行。