4-(2-噻唑基)苯酚 | 90563-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(2-噻唑基)苯酚
• 英文名称: 2-(4-Hydroxy-phenyl)-2-thiazolin
• 英文别名: 4-(4,5-dihydrothiazol-2-yl)phenol；2-(4-hydroxyphenyl)-2-thiazoline；2-(4-hydroxyphenyl)-4,5-dihydro-1,3-thiazole；4-(2-Thiazolin-2-YL)phenol；4-(4,5-dihydro-1,3-thiazol-2-yl)phenol
• CAS: 90563-68-1
• 化学式: C₉H₉NOS
• mdl: MFCD00085170
• 分子量: 179.243
• InChiKey: JDBUEZWQOCUAJT-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  164 °C(Press: 1.5 Torr)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-噻唑基)苯酚 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以94 %的产率得到2-(4-羟基苯基)噻唑
  参考文献：
  名称：

  使用香草醇氧化酶从 4-羟基苯甲醛化学酶法合成 2-芳基噻唑啉

  摘要：

  在香草醇氧化酶（VAO）存在下，通过自发缩合反应，由 4-羟基苯甲醛和氨基硫醇一锅合成 2-芳基噻唑啉，然后优先对原位生成的 CN 键进行酶促氧化（相对于其他竞争官能团） 。该生物催化剂表现出良好的底物耐受性，并且可以对酶产物进行化学修饰以扩大结构多样性。

  DOI：

  10.1002/anie.202405833
• 作为产物：
  描述：

  4-羟基硫代苯甲酰胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 水 为溶剂， 反应 2.5h， 以90%的产率得到4-(2-噻唑基)苯酚
  参考文献：
  名称：

  Back matter

  摘要：

  DOI：

  10.1039/c1gc90050a

文献信息

• Trichloroisocyanuric acid as an efficient homogeneous catalyst for the chemoselective synthesis of 2-substituted oxazolines, imidazolines and thiazolines under solvent-free condition
  作者：Fatemeh Hojati、Atefe Nezhadhoseiny

  DOI：10.2298/jsc111031028h

  日期：——

  Trichloroisocyanuric acid, as a commercially available and inexpen- sive catalyst, was used in a new, facile and efficient procedure for the synthesis of 2-oxazolines, 2-imidazolines and 2-thiazolines through the reaction of nitriles with 2-aminoethanol, ethylenediamine or 2-aminoethanеthiol under solvent-free conditions.

  三氯异氰尿酸是一种市售的廉价催化剂，它通过腈与2-氨基乙醇，乙二胺或乙腈的反应，以新颖，便捷，高效的方法合成了2-恶唑啉，2-咪唑啉和2-噻唑啉。在无溶剂条件下的2-氨基乙硫醇。
• 1,3-Dibromo-5,5-dimethylhydantoin as an efficient homogeneous catalyst for the synthesis of 2-arylthiazolines and 2-arylimidazolines
  作者：Seyedeh Fatemeh Hojati、Iraj Mohammadpoor-Baltork、Behrooz Maleki、Mostafa Gholizadeh、Fatemeh Shafiezadeh、Mahnaz Haghdoust

  DOI：10.1139/v09-144

  日期：2010.2

  A simple, facile, and efficient procedure for the synthesis of 2-arylthizolines and 2-arylimidazolines has been developed by the simple condensation of nitriles with 2-aminoethanethiol or ethylenediamine catalyzed by 1,3-dibromo-5,5-dimethylhydantoin under solvent-free conditions. Selective preparation of bisthiozolines and monoimidazolines from dinitriles and also selective conversion of arylnitriles to their corresponding 2-arylthiazolines or imidazolines in the presence of alkylnitriles can be considered as considerable advantages of this method.

  在无溶剂条件下，通过 1,3-二溴-5,5-二甲基海因催化腈类与 2-氨基乙硫醇或乙二胺的简单缩合，开发出了一种简单、方便、高效的 2-芳基噻唑啉类和 2-芳基咪唑啉类的合成方法。从二腈纶中选择性地制备双噻唑啉类和单咪唑啉类化合物，以及在烷基腈的存在下选择性地将芳基腈转化为相应的 2-芳基噻唑啉类或咪唑啉类化合物，可以说是这种方法的一大优势。
• Easy access to thiazolines and thiazines via tandem S-alkylation-cyclodeamination of thioamides/haloamines
  作者：Uma Pathak、Shubhankar Bhattacharyya、Vishwanath Dhruwansh、Lokesh Kumar Pandey、Rekha Tank、Malladi V. S. Suryanarayana

  DOI：10.1039/c1gc15285h

  日期：——

  This is the first report of a facile synthesis of thiazolines and thiazines from a self-catalyzed, water assisted tandem S-alkylation-cyclodeamination reaction of thioamides/haloamines. The reaction is clean and efficient with simple product work-up, and is applicable to a variety of substrates.

  这是首次报道通过硫代酰胺/卤胺的自催化、水辅助串联 S-烷基化-环脱氨基反应简便合成噻唑啉类和噻嗪类化合物。该反应清洁高效，产物处理简单，适用于多种底物。
• The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors
  作者：Anna Minkkilä、Mikko J. Myllymäki、Susanna M. Saario、Joel A. Castillo-Melendez、Ari M.P. Koskinen、Christopher J. Fowler、Jukka Leppänen、Tapio Nevalainen

  DOI：10.1016/j.ejmech.2009.01.007

  日期：2009.7

  A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC(50)s: 0.0063 and 0.012 mu M) and the low-micromolar ranges (IC(50)s; 2.1 and 1.0 mu M), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 mu M) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations >= 0.030 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.
• ROBBE, Y.;FERNANDEZ, J. -P.;CHAPAT, J. -P.;SENTENAC-ROUMANOU, H.;FATOME, +, EUR. J. MED. CHEM., 1985, 20, N 1, 16-24
  作者：ROBBE, Y.、FERNANDEZ, J. -P.、CHAPAT, J. -P.、SENTENAC-ROUMANOU, H.、FATOME, +

  DOI：——

  日期：——