2-(2-苯并噻唑)-5-甲基苯酚 | 56048-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(2-苯并噻唑)-5-甲基苯酚
• 英文名称: 2-(benzo[d]thiazol-2-yl)-5-methylphenol
• 英文别名: 2-(2-Benzothiazolyl)-5-methylphenol；2-(1,3-benzothiazol-2-yl)-5-methylphenol
• CAS: 56048-54-5
• 化学式: C₁₄H₁₁NOS
• mdl: MFCD00043783
• 分子量: 241.313
• InChiKey: DILRSGGQTSJRST-UHFFFAOYSA-N

物化性质

• 沸点：
  410.6±55.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-苯并噻唑)-5-甲基苯酚 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 16.0h， 生成 2-[2-[(methoxymethyl)oxy]-4-(bromomethyl)phenyl]benzothiazole
  参考文献：
  名称：

  Antimicrobial effects of novel siderophores linked to β-lactam antibiotics

  摘要：

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00261-8
• 作为产物：
  描述：

  2-(4-甲基苯基)苯并噻唑 在 三氯溴甲烷 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 氧气 、 palladium diacetate 作用下， 以 环己烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以62%的产率得到2-(2-苯并噻唑)-5-甲基苯酚
  参考文献：
  名称：

  金属氧还原介导的好氧条件下芳烃的C sp2 - H羟基化

  摘要：

  据报道，通过有机光氧化还原和金属催化作用的结合，2-芳基吡啶和2-芳基苯并噻唑的直接羟基化反应，其中4CzIPN被用作可见光光催化剂，而Pd（OAc）2被用作金属催化剂。该方法已被用于合成表现出激发态分子内质子转移性质的有机分子，以产生可调节的发光响应。

  DOI：

  10.1021/acs.orglett.8b01973

文献信息

• Correlation between molecular structure and optical properties for the bis(2-(2-hydroxyphenyl)benzothiazolate) complexes
  作者：Xu Huixia、Xu Bingshe、Fang Xiaohong、Chen Liuqing、Wang Hua、Hao Yuying

  DOI：10.1016/j.jphotochem.2010.09.026

  日期：2011.1

  A series of methyl-substituted bis(2-(hydroxyphenyl)benzothiazolate)zinc derivatives [Zn(n-MeBTZ)2, n = 3 (1a), 4 (1b), 5 (1c)] were synthesized to investigate the correlation between molecular structures and optical properties. The results indicate that the blue-emitting (λmax = 470 nm) complex 1b is monomer with a higher PL quantum efficiency than complexes 1, 1a, 1c. Two green-emitting (λmax = 507 nm

  合成了一系列甲基取代的双（2-（羟苯基）苯并噻唑酸盐）锌衍生物[Zn（n -MeBTZ）2，n  = 3（1a），4（1b），5（1c）]，以研究它们之间的相关性。分子结构和光学性质。结果表明，蓝色发光（λ最大 = 470纳米）复杂1B是具有比配合物更高的PL量子效率单体1，1A，1C。两个绿色发光（λ最大 = 507纳米和499纳米）配合物1A和1C具有特殊的双分子结构。Zn（BTZ）2（配合物1）的分子结构为二聚体。通过使用这些络合物作为发光层来制造双层有机发光器件。器件的最大发射波长在501–553 nm范围内。该器件示出了在9.2，12.7，2.3和10.7 V电源导通电压复杂1，1A，1B，和1C分别。特别地，在相同条件下，具有配合物1b的装置显示出比其他配合物更高的亮度。
• Direct Oxygenation of C–H Bonds through Photoredox and Palladium Catalysis
  作者：Sk. Sheriff Shah、Maniklal Shee、Amit Kumar Singh、Amrita Paul、N. D. Pradeep Singh

  DOI：10.1021/acs.joc.9b03197

  日期：2020.3.6

  This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole

  该报告介绍了通过光催化和Pd催化相结合的CH键的氧合。在这里，我们描述了利用光催化剂将有机钯（II）中间体氧化为高价PdIII或PdIV中间体，从而促进CO键的形成。所证明的方法可以有效地与各种导向基团一起使用，例如肟醚和苯并噻唑。通过合成可用于有机发光二极管和药物的2-（苯并[d]噻唑-2-基）苯酚的几种金属配合物，表明了这种直接CO键形成方法的适用性。
• Unified synthesis of mono/bis-arylated phenols via Rh^III-catalyzed dehydrogenative coupling
  作者：Qian Wu、Ying Chen、Dingyuan Yan、Muyue Zhang、Yi Lu、Wei-Yin Sun、Jing Zhao

  DOI：10.1039/c6sc03169b

  日期：——

  precise control of the oxidation pathways so that directing groups can be either preserved or cleaved. We found that N-phenoxyacetamides could undergo ortho-arylation reactions with or without an external oxidant, yielding products with different oxidation states, notably the rare bis-arylated phenols. Notably, a unique rhodacycle intermediate was isolated, characterized by X-ray crystallography, and

  2,6-双芳基化的苯酚很少报道，并且具有合成挑战性。使用指导基团（DG）进行的指导的C–H功能化反应可能为其合成提供便利的解决方案。但是，这种策略通常会导致导向基团的部分裂解，从而阻止进一步的/第二次C–H激活级联反应。本文中，我们报告了一种总体策略，该策略允许精确控制氧化途径，以便可以保留或裂解导向基团。我们发现N-苯氧基乙酰胺可以经历邻位-有或没有外部氧化剂的-芳基化反应，产生具有不同氧化态的产物，特别是稀有的双芳基化酚。值得注意的是，分离出独特的rhodocycle中间体，通过X射线晶体学表征，并证实是活性催化剂。内部和外部氧化之间的转换可能是实现多种双官能化H-官能化反应的通用策略。
• Synthesis of bioactive 2-(2-(difluoromethoxy)aryl)benzo[d]thiazole derivatives via base-promoted one-pot process
  作者：Huiping Zeng、Puying Luo、Manling Luo、Hao Ding、Qiuping Ding

  DOI：10.1016/j.tet.2019.130472

  日期：2019.8

  A convenient synthesis of 2-(2-(difluoromethoxy)aryl)benzo[d]thiazoles from 2- (o-hydroxyaryl)benzothiazoles and commercially available ethyl difluoroiodoacetate (ICF2CO2Et) is described. The transformation was amenable to a one-pot, sequential three-component protocol from o-hydroxybenzaldehyde, o-aminothiophenol, and ICF2CO2Et promoted by KOH. Additionally, some of the prepared compounds exhibited

  描述了由2-（邻-羟基芳基）苯并噻唑和可商购的二氟碘乙酸乙酯（ICF 2 CO 2 Et）方便地合成2-（2-（二氟甲氧基）芳基）苯并[d]噻唑的方法。变换为适合于从一釜，顺序三组分协议ö羟基苯甲醛，ø -aminothiophenol，和ICF 2 CO 2的Et促进由KOH。另外，一些制备的化合物对人卵巢癌细胞显示出有希望的活性。
• 一种杂环类化合物及合成方法
  申请人：三峡大学

  公开号：CN106699777B

  公开（公告）日：2019-01-15

  本发明属于有机化工技术领域，特别是一种新型杂环化合物，所述杂环化合物的化学结构式为：其中，取代基R1和R2为氢或烷基或硝基或卤素或醛基，取代基位置、个数不固定。合成方法为以苯并噻唑类衍生物、溴化腈和碱一步法、无催化剂，得到的一类新型杂环化合物化合物，关键点在于一步法、无催化剂和温和反应条件的合成新方法，又因其杂环结构，有利于在生物体内活性的应用。

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