2-(phenoxymethyl)benzoxazole | 7506-48-1

• 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: 2-(phenoxymethyl)benzoxazole
• 英文别名: 2-(phenoxymethyl)benzo[d]oxazole；2-(Phenoxymethyl)-1,3-benzoxazole
• CAS: 7506-48-1
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: IUSYEIUXPASPBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(phenoxymethyl)benzoxazole 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2-氨基苯酚
  参考文献：
  名称：

  Cohn, Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 294

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-hydroxyphenyl)-2-phenoxyacetamide 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成 2-(phenoxymethyl)benzoxazole
  参考文献：
  名称：

  A microwave assisted synthesis of benzoxazoles from carboxylic acids

  摘要：

  A series of various poly-substituted benzoxazoles were synthesized starting from readily available carboxylic acids. The method is based on TCT (cyanuric chloride)/microwave acid activation and it is characterized by mild conditions, allowing for a wide range of starting materials and functionalization of final products. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.084

文献信息

• Microwave-Assisted Direct Synthesis of 2-Substituted Benzoxazoles from Carboxylic Acids under Catalyst and Solvent-Free Conditions
  作者：Asit K. Chakraborti、Raj Kumar、C. Selvam、Gurmeet Kaur

  DOI：10.1055/s-2005-868509

  日期：——

  A direct coupling of carboxylic acids with 2-aminophenol under microwave irradiation has been achieved leading to the synthesis of 2-substituted benzoxazoles under metal and solvent-free conditions. Aliphatic, aromatic and heteroaromatic carboxylic acids provide good yields. Benzoxazole formation takes place in the presence of chloro, methoxy, phenoxy, thiophenoxy, and α,β-unsaturated functionalities. In the case of dicarboxylic acids, the reaction proceeds via the formation of the corresponding anhydride with predominant formation of the mono-benzoxazole.

  在微波辐射下，羧酸与2-氨基苯酚直接耦合，实现了无金属和溶剂条件下的2-取代苯并恶唑合成。脂肪族、芳香族和杂芳香族羧酸均可提供良好的产率。苯并恶唑的形成在氯、甲氧基、苯氧基、噻吩氧基和α,β-不饱和功能团的存在下发生。对于二元羧酸，反应通过形成相应的酸酐进行，主要生成单苯并恶唑。
• One-Pot Synthesis of 2-Substituted Benzoxazoles Directly from Carboxylic Acids
  作者：Dinesh Kumar、Santosh Rudrawar、Asit K. Chakraborti

  DOI：10.1071/ch08193

  日期：——

  Methanesulfonic acid has been found to be a highly effective catalyst for a convenient and one-pot synthesis of 2-substituted benzoxazoles by the reaction of 2-aminophenol with acid chlorides, generated in situ from carboxylic acids. Aryl, heteroaryl, and arylalkyl carboxylic acids provided excellent yields of the corresponding benzoxazoles. The reaction conditions were compatible with various substituents

  已发现甲磺酸是一种高效的催化剂，可通过 2-氨基苯酚与由羧酸原位生成的酰氯反应方便地一锅合成 2-取代的苯并恶唑。芳基、杂芳基和芳烷基羧酸提供了相应苯并恶唑的优异产率。反应条件与各种取代基如氯、溴、硝基、甲氧基、环戊氧基、苯氧基、噻吩氧基和共轭双键相容。发现苯并恶唑的形成通常与取代的 2-氨基苯酚有关。
• Synthesis and structure–activity relationships of new antimicrobial active multisubstituted benzazole derivatives
  作者：Ilkay Yildiz-Oren、Ismail Yalcin、Esin Aki-Sener、Nejat Ucarturk

  DOI：10.1016/j.ejmech.2003.11.014

  日期：2004.3

  benzothiazole ring system enhanced the antimicrobial activity against Staphylococcus aureus. In these sets of non-nucleoside fused heterocyclic compounds electron withdrawing groups at position 5 of the benzazoles increased the activity against C. albicans.

  合成了一系列多取代的苯并恶唑，苯并咪唑和苯并噻唑（5-7）作为非核苷稠合的等排杂环化合物，并测试了它们对各种革兰氏阳性和革兰氏阴性细菌的抗菌活性以及对白色念珠菌的抗菌活性。微生物学结果表明，所合成的化合物在MIC值为100至3.12 microg / ml的范围内具有针对被测微生物的广谱活性。结构-活性关系（SAR）研究表明，苯并噻唑环系统增强了对金黄色葡萄球菌的抗菌活性。在这些非核苷稠合的杂环化合物中，苯并恶唑的5位吸电子基团增加了对白色念珠菌的活性。
• Synthesis, Antifungal Activities and Molecular Docking Studies of Benzoxazole and Benzothiazole Derivatives
  作者：Bo Luo、Ding Li、An-Ling Zhang、Jin-Ming Gao

  DOI：10.3390/molecules23102457

  日期：——

  an important pharmacophore, two series of 2-(aryloxymethyl) benzoxazole and benzothiazole derivatives were synthesized and their antifungal effects against eight phytopathogenic fungi were evaluated. Compounds 5a, 5b, 5h, and 5i exhibited significant antifungal activities against most of the pathogens tested. Especially 5a, 5b, 5h, 5i, 5j, and 6h inhibited the growth of F. solani with IC50 of 4.34⁻17

  以苯并恶唑和苯并噻唑支架为重要药效基团，合成了两个系列的2-（芳氧基甲基）苯并恶唑和苯并噻唑衍生物，并评价了它们对八种植物病原真菌的抗真菌作用。化合物5a，5b，5h和5i对大多数测试的病原体均表现出显着的抗真菌活性。尤其是5a，5b，5h，5i，5j和6h抑制了茄形假丝酵母的生长，IC50为4.34±17.61μg/ mL，强于阳性对照羟氨唑（IC50为38.92μg/ mL）。5h是最有效的针对F. Solani的抑制剂（IC50为4.34μg/ mL），其效力是羟甲唑的约9倍。大多数测试化合物对灰葡萄孢均表现出显着的抗真菌作用（IC50为19.92⁻77.41μg/ mL），其中5a是最好的一种（IC50为19.92μg/ mL）。比较了结构-活性关系（SAR）。结果表明，电子吸引能力和取代基的位置对生物活性具有重要影响。此外，对酿酒酵母的脂质转移蛋白sec14p进行了对接研究，初步
• Metal-free direct annulation of 2-aminophenols and 2-aminothiophenols with unactivated amides through transamidation: Access to polysubstituted benzoxazole and benzothiazole derivatives
  作者：Vishal Kumar、Sanjeev Dhawan、Renu Bala、Pankaj Sanjay Girase、Parvesh Singh、Rajshekhar Karpoormath

  DOI：10.1016/j.tet.2022.132794

  日期：2022.6

  hydrochloride played a crucial role in amide activation followed nucleophilic attack that through eliminations of amine as a side product, and de-hydrolysis step leads to final annulation. This versatile strategy is applicable to a wide variety of differently substituted o-aminophenols, unactivated aliphatic and aromatic amides, yielding the corresponding product in good to excellent yields in a single step

  我们在此报告了一种简单而新颖的氧化剂、金属和无溶剂绿色方案，用于从 2-氨基苯酚盐酸盐非活化酰胺作为原位碳源合成不同的 2-取代的 1,3-苯并恶唑和苯并噻唑。此外，盐酸盐的氢离子在亲核攻击后的酰胺活化中起关键作用，亲核攻击通过消除胺作为副产物，脱水解步骤导致最终的环化。这种通用策略适用于多种不同取代的邻氨基苯酚、未活化的脂肪族和芳香族酰胺，只需一步即可以良好至极好的收率生产相应的产品。