2-氯-4-(4-氯苯基)噻唑 | 2103-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-氯-4-(4-氯苯基)噻唑
• 英文名称: 2-chloro-4-(4-chlorophenyl)thiazole
• 英文别名: 2-chloro-4-(4-chlorophenyl)-1,3-thiazole
• CAS: 2103-96-0
• 化学式: C₉H₅Cl₂NS
• mdl: MFCD08446725
• 分子量: 230.117
• InChiKey: RVWSKHMFWGXGQW-UHFFFAOYSA-N

物化性质

• 熔点：
  97-101 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 危险品标志：
  T
• 安全说明：
  S26,S36/37/39,S45
• 危险标志：
  GHS05,GHS06
• 危险类别码：
  R25,R37/38,R41
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 危险性描述：
  H301,H315,H318,H335,H413
• 危险性防范说明：
  P261,P280,P301 + P310,P305 + P351 + P338
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2-氯-4-(4-氯苯基)噻唑 在 盐酸肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 4-(4-氯苯基)-2-肼基-1,3-噻唑
  参考文献：
  名称：

  Mahajan,M.P. et al., Australian Journal of Chemistry, 1977, vol. 30, p. 2053 - 2056

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲酰甲基硫氰酸酯 在 盐酸 、 乙醚 作用下， 生成 2-氯-4-(4-氯苯基)噻唑
  参考文献：
  名称：

  Bariana et al., Journal of the Indian Chemical Society, 1955, vol. 32, p. 427,428, 429

  摘要：

  DOI：

文献信息

• Synthesis and structure–activity relationship of aminoarylthiazole derivatives as correctors of the chloride transport defect in cystic fibrosis
  作者：Emanuela Pesce、Marta Bellotti、Nara Liessi、Sara Guariento、Gianluca Damonte、Elena Cichero、Andrea Galatini、Annalisa Salis、Ambra Gianotti、Nicoletta Pedemonte、Olga Zegarra-Moran、Paola Fossa、Luis J.V. Galietta、Enrico Millo

  DOI：10.1016/j.ejmech.2015.05.030

  日期：2015.6

  targeted by small molecules called generically correctors and potentiators, respectively. Aminoarylthiazoles (AATs) represent an interesting class of compounds that includes molecules with dual activity, as correctors and potentiators. With the aim to improve the activity profile of AATs, we have now designed and synthesized a library of novel compounds in order to establish an initial SAR that may provide

  囊性纤维化跨膜电导调节剂 (CFTR) 是存在于上皮细胞膜中的氯离子通道。影响CFTR的突变基因导致囊性纤维化（CF），一种多器官严重疾病。最常见的 CF 突变 F508del 会损害 CFTR 蛋白的加工和活性（门控）。其他突变，如 G551D，只会导致门控缺陷。加工和门控缺陷可以分别被称为一般校正剂和增强剂的小分子作为目标。氨基芳基噻唑 (AAT) 代表了一类有趣的化合物，包括具有双重活性的分子，作为校正剂和增强剂。为了改善 AAT 的活性特征，我们现在设计并合成了一个新化合物库，以建立一个初始 SAR，该 SAR 可以提供有关对救援活动有益或有害的化学基团的指示。使用功能测定法在表达 CFBE41o 的 F508del-CFTR 中测试了新化合物作为校正剂和增强剂。双重活性化合物 AAT-如图 4a 所示，当与校正剂 VX-809 组合时，其特征在于提高的功效和显着的协同作用。此外，通过计算方法，已检测到核苷酸结合域
• Laccase-Catalysed Homocoupling of Primary Aromatic Amines towards the Biosynthesis of Dyes
  作者：Ana Catarina Sousa、Lígia O. Martins、M. Paula Robalo

  DOI：10.1002/adsc.201300501

  日期：2013.10.11

  AbstractColoured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p‐electron donor primary aromatic amines using two different laccases, CotA‐laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange‐red to purple products, presenting high molar extinction coefficients, presumably result from oxidative homocoupling reactions, through the formation of NC bonds at positions 2 and 5, of the laccase oxidised intermediate as showed in the proposed oxidative pathway. The product of 1,4‐phenylenediamine is shown to be the trimer known as Bandrowski’s base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p‐electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data contribute for (i) understanding key features of laccase reactivity with p‐substituted aromatic amines and (ii) establishing enzymatic processes that lead to the synthesis of coloured bio‐products under mild conditions with potential impact in the cosmetic and dye industries.magnified image
• Convenient and Reliable Routes Towards 2-Aminothiazoles: Palladium-Catalyzed<i>versus</i>Copper-Catalyzed Aminations of Halothiazoles
  作者：Stéphanie Toulot、Timo Heinrich、Frédéric R. Leroux

  DOI：10.1002/adsc.201300591

  日期：2013.11.11

  AbstractTwo efficient methods for the amination of 2‐halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2‐aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium‐catalyzed CN coupling reactions between 2‐halothiazoles and primary alkylamines are presented. In a second part, ligand‐free copper‐catalyzed aminations of 2‐halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2‐halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2‐aminothiazoles, key molecules in pharmaceutical research.magnified image
• NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
  作者：Giorgio Chelucci、Susanna Figus

  DOI：10.1016/j.molcata.2014.06.012

  日期：2014.11
• Singh,H. et al., Indian Journal of Chemistry, 1966, vol. 4, p. 527 - 528
  作者：Singh,H. et al.

  DOI：——

  日期：——