3-苯并噁唑-2-苯酚 | 3164-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-苯并噁唑-2-苯酚
• 中文别名: 3-(苯并[D]恶唑-2-基)苯酚
• 英文名称: 3-(benzo[d]oxazol-2-yl)phenol
• 英文别名: 3-(1,3-benzoxazol-2-yl)phenol；2-(3-hydroxyphenyl)-1,3-benzoxazole；2-(3-hydroxyphenyl)benzoxazole
• CAS: 3164-06-5
• 化学式: C₁₃H₉NO₂
• 分子量: 211.22
• InChiKey: QHUYLIOMTFQOSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-苯并噁唑-2-苯酚 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 3-(1-(3-(3-(benzo[d]oxazol-2-yl)phenoxy)propyl)piperidin-4-yl)-6-fluorobenzo[d]isoxazole
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of piperidine (piperazine)-substituted benzoxazole derivatives as multi-target antipsychotics

  摘要：

  The present study describes the optimization of a series of novel benzoxazole-piperidine (piperazine) derivatives combining high dopamine D-2 and serotonin 5-HT1A, 5-HT2A receptor affinities. Of these derivatives, the pharmacological features of compound 29 exhibited high affinities for the DA D-2, 5-HT1A and 5-HT2A receptors, but low affinities for the 5-HT2C and histamine H-1 receptors and human ether-a-go-go-related gene (hERG) channels. Furthermore, compound 29 reduced apomorphine-induced climbing and 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI)-induced head twitching without observable catalepsy, even at the highest dose tested. Thus, compound 29 is a promising candidate as a multi-target antipsychotic treatment. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.045
• 作为产物：
  描述：

  3-nitrobenzylidene-2-aminophenol 在 盐酸 、 nickel(II) chloride hexahydrate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 9.92h， 生成 3-苯并噁唑-2-苯酚
  参考文献：
  名称：

  2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms

  摘要：

  The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 mu g/ml; MIC(LORA) 2.06 and 1.59 mu g/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 mu M respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 mu M respectively) followed by the Vit-K2 rescue study and ATP production assay.

  DOI：

  10.1016/j.bioorg.2020.104170
• 作为试剂：
  描述：

  、 4-苯并噁唑-2-苯酚 、 2-(2-羟苯基)苯并恶唑 、 2-(3-Chloro-4-hydroxyphenyl)benzoxazole 、 2-(3-Methyl-4-hydroxyphenyl)benzoxazole 、 4-(1,3-苯并恶唑-2-基)-2,6-二甲基苯酚 、 2-(3,5-Dichloro-4-hydroxyphenyl)benzoxazole 、 2-(3,5-dimethoxy-4-hydroxyphenyl)benzoxazole 、 、 2-(2,6-Dichloro-4-hydroxyphenyl)benzoxazole 、 2-(2,6-Dimethyl-4-hydroxyphenyl)benzoxazole 在 3-苯并噁唑-2-苯酚 作用下， 生成 4-(2-[4-(2-Benzoxazolyl)phenoxy]ethoxy)-2-hydroxybenzophenone
  参考文献：
  名称：

  Multichromophoric ultraviolet stabilizers and their use in organic

  摘要：

  本发明涉及多色团化合物，发现其有效地作为紫外线稳定剂。本发明还涉及含有稳定剂量的多色团化合物的紫外线可降解有机组成物，以防止这种降解。这些稳定剂在聚合物组成物中存在其他常用添加剂的情况下有效，包括颜料、染料、填料、增强剂等。这些紫外线稳定剂也可以在聚合物熔融中或溶解在聚合物溶液中，涂覆在成型物、薄膜或挤出纤维的外部中。

  公开号：

  US04115348A1

文献信息

• A ball-milling strategy for the synthesis of benzothiazole, benzimidazole and benzoxazole derivatives under solvent-free conditions
  作者：Hemant Sharma、Narinder Singh、Doo Ok Jang

  DOI：10.1039/c4gc01142b

  日期：——

  A convenient solvent-free method for the synthesis of benzothiazole, benzimidazole, and benzoxazole derivatives has been developed using recyclable ZnO-NPs via a ball-milling strategy. The method affords environmentally friendly reaction conditions that score high on the ecoscale with the low E-factor. The process is also highly efficient even on a multi-gram scale and provides easy product isolation

  通过球磨策略，使用可回收的ZnO-NP ，开发了一种方便的无溶剂合成苯并噻唑，苯并咪唑和苯并恶唑衍生物的方法。该方法提供了对环境友好的反应条件，该条件在生态规模上得分很高，而E因子却很低。该过程即使在几克规模的情况下也非常高效，并且可以轻松实现产品隔离。
• Magnetically separable nano CeO2: a highly efficient catalyst for ligand free direct C–H arylation of heterocycles
  作者：Radheshyam S. Shelkar、Kishor E. Balsane、Jayashree M. Nagarkar

  DOI：10.1016/j.tetlet.2014.12.069

  日期：2015.1

  An efficient, ligand free, nano CeO2–Fe3O4 catalyzed direct C–H arylation of heteroarenes such as benzoxazole and benzothiazole has been carried out with aryl halides in DMSO or arenediazonium salts in water. The catalyst exhibited high activity with moderate to excellent product yields under mild reaction conditions. Nano CeO2–Fe3O4 was synthesized and characterized by SEM, TEM, EDAX, XRD, FTIR, DSC-TGA

  一种有效的，无配体的纳米CeO 2 -Fe 3 O 4催化杂芳烃如苯并恶唑和苯并噻唑的直接C–H芳基化反应已在DMSO中使用了芳基卤化物或在水中使用了芳族重氮盐。在温和的反应条件下，该催化剂表现出高活性并具有中等至优异的产物收率。合成了纳米CeO 2 –Fe 3 O 4并通过SEM，TEM，EDAX，XRD，FTIR，DSC-TGA和ICP-MS对其进行了表征。即使经过十次循环再利用，催化剂的催化活性和稳定性也非常好
• Tuning the Excited State of Tetradentate Pd( <scp>II</scp> ) and Pt( <scp>II</scp> ) Complexes through Benzannulated <scp> <i>N</i> ‐Heteroaromatic </scp> Ring and Central Metal
  作者：Guijie Li、Hua Guo、Xiaoli Fang、Yun‐Fang Yang、Yulu Sun、Weiwei Lou、Qisheng Zhang、Yuanbin She

  DOI：10.1002/cjoc.202100641

  日期：2022.1.15

  excited-state properties of the Pd(II) and Pt(II) complexes. In identical condition, compared to pbiz-based Pd(II) and Pt(II) complexes, the corresponding metal complexes with pboz and pbthz-containing ligand show significant red-shift emission spectra. Pd(II) complexes exhibit blue-shift emission spectra in comparison with the corresponding Pt(II) complexes. The Pt(II) complexes possess more metal-to-ligand

  一系列四齿Pd(II)和Pt(II)配合物，含有5/6/6金属环与苯基N-杂芳基苯并[ d ]咪唑( pbiz )、苯并[ d ]恶唑( pboz )或苯并[ d ]噻唑( pbthz ) 含配体被开发出来。通过实验和理论计算的系统研究表明，中心金属和苯并环化的N-杂芳环对 Pd(II) 和 Pt(II) 配合物的电化学、光物理和激发态性质有显着影响。在相同条件下，与pbiz相比基于 Pd(II) 和 Pt(II) 的配合物，相应的金属配合物与含pboz和pbthz的配体显示出显着的红移发射光谱。与相应的 Pt(II) 配合物相比，Pd(II) 配合物表现出蓝移发射光谱。Pt(II) 配合物在其 T 1状态下具有更多的金属到配体电荷转移 ( 3 MLCT ) 特性，这使得 Pt(II) 配合物具有更高的量子效率 ( Φ PL ) 和更短的激发态寿命( τ )，导致大的辐射衰减率 ( k r
• Graphene Oxide as a Heterogeneous Reagent Promoted Synthesis of 2-Substituted 1,3-Benzazoles in Water
  作者：Dariush Khalili、Ali Reza Banazadeh

  DOI：10.1246/bcsj.20150232

  日期：2015.12.15

  An efficient chemical method for the synthesis of benzimidazoles, benzothiazoles, and benzoxazoles has been developed through the condensation of various aldehydes with o-phenylenediamine, o-aminothiophenol, and o-aminophenol using graphene oxide (GO) as an oxidant in water. These benzazoles are also prepared through a one-pot oxidation/condensation tandem process by reacting alcohols with 2-amino(thio)phenol/aniline in the presence of GO in poly(ethylene glycol) as a safe media. Moreover, this carbonaceous material could be readily separated using a simple filtration.

  一种高效的化学方法已被开发，用于合成苯并咪唑、苯并噻唑和苯并噁唑，该方法通过将各种醛与邻苯二胺、邻氨基硫酚和邻氨基酚在水中以氧化石墨烯 (GO) 为氧化剂进行缩合反应。这些苯并杂环化合物还可以通过在聚乙烯 glycol 中以 GO 为介质，使用醇与 2-氨基(硫)苯酚/苯胺进行一锅氧化/缩合串联反应来制备。此外，这种碳质材料可以通过简单的过滤方法轻松分离。
• A Mild, Efficient and Reusable Solid Phosphotungestic Acid Catalyst Mediated Synthesis of Benzoxazole Derivatives: A Grinding Approach
  作者：Mahadeo R. Patil、Aditya Yelamaggad、Rangappa S. Keri

  DOI：10.2174/2212717803666160728170600

  日期：2016.10.25

  Background: The development of efficient methodologies for the preparation of benzoxazole and its derivatives has gained a lot of importance in current research. There are many methods are reported for the synthesis of benzoxazoles includes condensation of 2-aminophenol with carboxylic acid. Traditional methods also have several side reactions, non renewable oxidative reagents and solvents which negatively

  背景：用于制备苯并恶唑及其衍生物的有效方法学的发展在当前研究中已变得非常重要。据报道，有许多方法合成苯并恶唑，包括2-氨基苯酚与羧酸的缩合反应。传统方法还具有多种副反应，不可再生的氧化剂和溶剂，它们会对反应的环境和生态友好性质产生负面影响。我们已经开发出PTA催化的2-亚氨基苯酚与不同的芳族醛，使用研磨策略以优异的收率合成2-芳基苯并恶唑。 方法：以二氧化硅为载体的PTA / PTA为固体酸催化剂，室温下通过研磨法高产率合成苯并恶唑。 结果：还研究了具有给电子或吸电子基团的芳香醛，预期该产品能很好地提高产品收率，可以看出给电子和吸电子基团的作用产率没有差异。 结论：我们已经开发了PTA催化的2-亚氨基苯酚与不同的芳族醛类通过研磨策略以优异的收率合成2-芳基苯并恶唑。在无溶剂条件下使用这种可重复使用的催化剂已使该方案实用，环保且在经济上具有吸引力。后处理简单，反应时间短，反应条件温和，产物收