2,5-dimethylthiazolo<3,2-b>-s-triazole | 26542-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并噻唑类
• 英文名称: 2,5-dimethylthiazolo<3,2-b>-s-triazole
• 英文别名: 2,6-Dimethyl[1,3]thiazolo[3,2-b][1,2,4]triazole；2-methyl-5-methylthiazolo[3,2-b]-1,2,4-triazole；2,6-dimethyl-thiazolo[3,2-b][1,2,4]triazole；2,5-Dimethylthiazolo<3,2-b>-1,2,4-triazol；2,6-Dimethylthiazolo[3,2-b][1,2,4]triazole；2,6-dimethyl-[1,3]thiazolo[3,2-b][1,2,4]triazole
• CAS: 26542-68-7
• 化学式: C₆H₇N₃S
• mdl: MFCD29912272
• 分子量: 153.208
• InChiKey: XTZJEHHMCQJAIT-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲苯硫酚 、 2,5-dimethylthiazolo<3,2-b>-s-triazole 在 copper(l) iodide 、 氧气 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以62%的产率得到5-(p-tolylthio)-2,6-dimethylthiazolo[3,2-b][1,2,4]triazole
  参考文献：
  名称：

  铜催化的噻唑并[3,2-b]-1,2,4-三唑与硫醇的区域选择性磺化

  摘要：

  为区域选择性铜催化的噻唑并 [3,2-b]-1,2,4-三唑与硫醇的直接磺基化开发了一个简单而有用的方案。该反应显示出广泛的官能团耐受性，并以中等至良好的产率快速获得磺基化噻唑并[3,2-b]-1,2,4-三唑。

  DOI：

  10.1055/s-0035-1562494
• 作为产物：
  描述：

  1-(5-methyl-1H-[1,2,4]triazol-3-ylsulfanyl)-propan-2-one 在 三氯氧磷 作用下， 以 xylene 为溶剂， 生成 2,5-dimethylthiazolo<3,2-b>-s-triazole
  参考文献：
  名称：

  1,2,4-Triazoles. XXVII. Synthesis of the thiazolo [2,3-c]-s-triazole and the thiazolo[3,2-b]-s-triazole systems

  摘要：

  DOI：

  10.1021/jo00800a004

文献信息

• SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS
  申请人：GLAXOSMITHKLINE LLC

  公开号：US20150152108A1

  公开（公告）日：2015-06-04

  The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本发明涉及新型取代桥式脲化合物，相应的相关类似物，药物组合物以及其使用方法。本发明的抑制素调节化合物可用于延长细胞寿命，并治疗和/或预防各种疾病和疾病，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块疾病、炎症、癌症和/或潮红有关的疾病或疾病，以及那些会受益于增加线粒体活性的疾病或疾病。本发明还涉及包含抑制素调节化合物与另一治疗剂组合的组合物。
• Palladium-Catalyzed Direct and Regioselective C-5 Desulfitative Arylation of Thiazolo[3,2-b]-1,2,4-triazoles with Sodium Sulfinates
  作者：Wenjie Liu、Shaohua Wang、Juan Lin、Yi Jiang、Qi Zhang、Yue Zhong

  DOI：10.1055/s-0033-1340320

  日期：——

  An efficient Pd(OAc) 2 -catalyzed direct arylation of thi­azolo[3,2- b ]-1,2,4-triazoles with sodium sulfinates has been developed. The reaction shows high regioselectivity, good reaction efficiency and excellent functional group compatibility. This approach provides a useful protocol for the preparation of functionalized thiazolo[3,2- b ]-1,2,4-triazole derivatives.

  已经开发了一种有效的 Pd(OAc) 2 -催化的噻唑并[3,2-b]-1,2,4-三唑与亚磺酸钠的直接芳基化反应。该反应显示出高区域选择性、良好的反应效率和优异的官能团相容性。该方法为制备功能化的噻唑并[3,2-b]-1,2,4-三唑衍生物提供了有用的方案。
• Silver-Catalyzed Direct Regioselective Phosphonation of Thiazolo[3,2-b]-1,2,4-triazoles with Dialkyl Phosphites
  作者：Shaohua Wang、Wenjie Liu、Ziying Li、Yanling Huang、Shenghao Li、Anda Wang

  DOI：10.1055/s-0035-1560495

  日期：——

  An efficient and generally applicable protocol for the silver-catalyzed direct phosphonation of thiazolo[3,2- b ]-1,2,4-triazoles with dialkyl phosphites has been developed. This transformation gives phosphonated products in moderate to good yields with high regioselectivity.

  已开发出一种有效且普遍适用的方案，用于用亚磷酸二烷基酯对噻唑并 [3,2-b]-1,2,4-三唑进行银催化直接磷酸化。这种转化以中等至良好的收率和高区域选择性得到膦酸化产物。
• Gas-phase pyrolysis of 4-amino-3-allylthio-1,2,4-triazoles: a new route to [1,3]thiazolo[3,2-b][1,2,4]triazoles
  作者：Dale D. J. Cartwright、Bernard A. J. Clark、Hamish McNab

  DOI：10.1039/b007638o

  日期：——

  Flash vacuum pyrolysis of the 3-allylthio derivatives of 4-amino-4H-1,2,4-triazoles 10–13 and 15–17 at 750–850 °C (10−2–10−3 Torr) gives [1,3]thiazolo[3,2-b][1,2,4]triazoles 19 and 24–29 in ca. 50% yield. The mechanism is thought to involve initial [3,3]sigmatropic shift of the allyl group, followed by cleavage of the N–N bond to generate a thiaza-allyl radical, which then undergoes cyclisation, rearrangement

  闪蒸真空热解在750-850°C（10 -2 -10 -3 Torr）下，4-氨基-4 H -1,2,4-三唑10-13和15-17的3-烯丙硫基衍生物的定量结果为[1,3]噻唑并[3,2- b ] [1,2,4]三唑19和24-29在约 收率50％。该机制被认为涉及初始的[3,3]σ向位移。烯丙基然后裂解N–N键生成噻唑-烯丙基自由基，然后进行 环化，重排和烷基 挤压。
• Highly regioselective ruthenium-catalyzed direct arylation of thiazolo[3,2-b]-1,2,4-triazoles with aryl iodides and aryl bromides via C–H bond activation
  作者：Huiping Zhang

  DOI：10.1016/j.jorganchem.2013.12.055

  日期：2014.4

  We have developed a convenient ruthenium-catalyzed direct arylation for highly regioselective synthesis of thiazolo[3,2-b]-1,2,4-triazole derivatives via C–H bond activation. This transformation has provided a new synthetic route to a variety of thiazolo[3,2-b]-1,2,4-triazoles and afforded desired products in good yields.

  我们已经开发了一种方便的钌催化直接芳基化反应，用于通过CH键激活来高度区域选择性合成噻唑并[3,2- b ] -1,2,4-三唑衍生物。这种转变为各种噻唑[3,2 - b ] -1,2,4-三唑提供了一条新的合成途径，并以高收率提供了所需的产物。