6-phenyl-5-(phenylthio)imidazo[2,1-b]thiazole | 400743-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-phenyl-5-(phenylthio)imidazo[2,1-b]thiazole
• 英文别名: 6-phenyl-5-phenylsulfanylimidazo[2,1-b][1,3]thiazole
• CAS: 400743-32-0
• 化学式: C₁₇H₁₂N₂S₂
• mdl: MFCD01080806
• 分子量: 308.428
• InChiKey: FFPOBAWQKMTVBX-UHFFFAOYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-苯基-咪唑并[2,1-b]噻唑 在 双氧水 、 碘 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 6-phenyl-5-(phenylthio)imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System

  摘要：

  Imidazoheterocycles undergo efficient and regioselective sulfenylation with disulfides using the iodine/hydrogen peroxide system in ethanol at 25 degrees C. This green strategy tolerates a wide range of functional groups to afford diverse sulfenylated imidazoheterocycles in high yields. Moreover, the fipronil (a pesticide) skeleton can be readily attached to imidazoheterocycles using this strategy, which is significant in drug development.

  DOI：

  10.1055/s-0034-1379941

文献信息

• Metal-free direct regioselective thiolation of imidazoheterocycles in water at room temperature
  作者：Dulin Kong、Qinghe Wang、Tiao Huang、Min Liang、Qiang Lin、Mingshu Wu

  DOI：10.1016/j.tet.2019.01.059

  日期：2019.3

  A metal-free direct thiolation of imidazoheterocycles with various thiophenol in water at room temperature has been developed. In addition, the chemistry provides several advantages including mild condition, high yields, good functional group tolerance, green solvents and suitable for large-scale operations.

  已开发出室温下在水中用各种硫酚对金属进行咪唑杂环的无金属直接硫醇化反应。此外，该化学方法还具有多种优势，包括条件温和，收率高，对官能团的耐受性好，绿色溶剂且适用于大规模操作。
• Unconventional Reactivity with DABCO-<i>Bis</i> (sulfur dioxide): C-H Bond Sulfenylation of Imidazopyridines
  作者：Julie Le Bescont、Chloé Breton-Patient、Sandrine Piguel

  DOI：10.1002/ejoc.202000112

  日期：2020.4.16

  Exploring the unexpected reactivity of DABCO‐bis(sulfur dioxide) on various imidazo[1,2‐a]pyridines expanded the toolbox of the sulfenylation reagent. Starting from three simple building blocks, this three‐component transformation led to various C‐3 sulfenylated substituted imidazo[1,2‐a]pyridines in moderate to good yields.

  探索DABCO-双（二氧化硫）在各种咪唑并[1,2- a ]吡啶上的出乎意料的反应性，扩大了亚磺酰化试剂的工具箱。从三个简单的结构单元开始，这种由三部分组成的转化以中等到良好的产率产生了各种C-3磺化取代的咪唑并[1,2- a ]吡啶。
• Copper-Catalyzed One-Pot Synthesis of Chalcogen-Benzothiazoles/Imidazo[1,2-a]pyridines with Sulfur/Selenium Powder and Aryl Boronic Acids
  作者：Tao Guo、Shu-Lei Han、Yong-Cheng Ma、Xu-Ning Wei、Ying-Li Zhu、Huan Chen

  DOI：10.1055/s-0037-1609758

  日期：2018.7

  An efficient and convenient copper-catalyzed oxidative chalcogenation of benzothiazoles and imidazo[1,2-a]pyridines with sulfur/selenium powder and aryl boronic acids was developed. This procedure allows access to a wide range of structurally diverse arylchalcogen-substituted benzothiazoles/imidazo[1,2-a]pyridines in good yields and with good functional group tolerance. A biological evaluation revealed

  开发了一种有效且方便的铜催化苯并噻唑和咪唑并 [1,2-a] 吡啶与硫/硒粉末和芳基硼酸的氧化硫属元素。该程序允许以良好的产率和良好的官能团耐受性获得各种结构多样的芳基硫属元素取代的苯并噻唑/咪唑并 [1,2-a] 吡啶。生物学评估表明，一些获得的产品在体外对人源性肺、胃、食管和乳腺癌细胞系具有抗增殖活性。
• Iodine–triphenylphosphine mediated sulfenylation of imidazoheterocycles with sodium sulfinates
  作者：Xuhu Huang、Shucheng Wang、Bowen Li、Xin Wang、Zemei Ge、Runtao Li

  DOI：10.1039/c4ra17237j

  日期：——

  An efficient approach to sulfenyl imidazoheterocycles has been developed via iodine–triphenylphosphine mediated direct sulfenylation of imidazoheterocycles with sodium sulfinates. The reactions proceed smoothly under transition-metal-free conditions with a broad range of substrate scope, giving the desired products in moderate to excellent yields.

  通过碘-三苯基膦介导的亚磺酸钠直接作用于咪唑杂环的亚磺酰基化，已开发出一种有效的亚磺酰基咪唑杂环杂环的方法。反应在无过渡金属条件下进行，且底物范围宽广，可以以中等至极好的收率得到所需的产物。
• Visible-Light-Induced Regioselective C–H Sulfenylation of Pyrazolo[1,5-<i>a</i>]pyrimidines via Cross-Dehydrogenative Coupling
  作者：Suvam Paul、Sourav Das、Tathagata Choudhuri、Papiya Sikdar、Avik Kumar Bagdi

  DOI：10.1021/acs.joc.2c02665

  日期：——

  methodology has been developed for the regioselective sulfenylation of pyrazolo[1,5-a]pyrimidine derivatives. Rose bengal, blue LEDs, KI, K2S2O8, and DMSO are all essential for this photocatalytic transformation. The protocol is applicable for the synthesis of a library of 3-(aryl/heteroaryl thio)pyrazolo[1,5-a]pyrimidine derivatives with broad functionalities. The selectivity and scalability of the methodology

  已开发出一种可见光诱导的交叉脱氢方法，用于吡唑并[1,5- a ]嘧啶衍生物的区域选择性硫化。玫瑰红、蓝色 LED、KI、K 2 S 2 O 8和 DMSO 对于这种光催化转化都是必不可少的。该协议适用于合成 3-(aryl/heteroaryl thio)pyrazolo[1,5- a]具有广泛功能的嘧啶衍生物。该方法的选择性和可扩展性也得到了证明。此外，该策略对吡唑、吲哚、咪唑并杂环化合物和 4-羟基香豆素进行磺酰化的效率已得到证实。机理研究揭示了基于自由基的机理和二芳基二硫化物的形成作为这种交叉脱氢偶联反应的关键中间体。