2-(3-噻吩基)-1,3-苯并噻唑 | 56421-77-3

• 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-(3-噻吩基)-1,3-苯并噻唑
• 英文名称: 2-(thiophen-3-yl)benzothiazole
• 英文别名: 2-(thiophen-3-yl)benzo[d]thiazole；2-(3-thienyl)benzothiazole；2-thiophen-3-yl-1,3-benzothiazole
• CAS: 56421-77-3
• 化学式: C₁₁H₇NS₂
• mdl: MFCD18451974
• 分子量: 217.315
• InChiKey: WJHVDQBJNAXATN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-噻吩基)-1,3-苯并噻唑 在 氯磺酸 、 五氯化磷 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 4-Benzothiazol-2-yl-thiophene-2-sulfonic acid (2-fluoro-ethyl)-amide
  参考文献：
  名称：

  Synthesis and structure-activity relationship of 4-(1,3-benzothiazol-2-yl)-thiophene-2-sulfonamides as cyclin-dependent kinase 5 (cdk5)/p25 inhibitors

  摘要：

  4-(1,3-Benzothiazol-2-yl)thiophene-2-sulfonamide (4a) was found to be a moderately potent inhibitor of cyclin-dependent kinase 5 (cdk5) from a HTS screen. The synthesis and SAR around this hit is described. The X-ray coordinates of ligand 4a with cdk5 are also reported, showing an unusual binding mode to the hinge region via a water molecule.

  DOI：

  10.1016/j.bmcl.2012.07.068
• 作为产物：
  描述：

  苯并噻唑 在 tris(dibenzylideneacetone)dipalladium (0) 正丁基锂 、 四溴化碳 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 6.0h， 生成 2-(3-噻吩基)-1,3-苯并噻唑
  参考文献：
  名称：

  An efficient palladium catalyzed synthesis of 2-arylbenzothiazoles

  摘要：

  A novel and convergent palladium catalyzed synthesis of 2-arylbenzothiazoles has been investigated. The key step in the synthesis is a Suzuki biaryl coupling of 2-bromobenzothiazole with aryl boronic acids to provide a variety of 2-arylbenzothiazole derivatives in good yield. The synthetic utility of this methodology is demonstrated by the synthesis of 2-(4-aminophenyl)-6-methoxybenzothiazole, a PET probe precursor for the in vivo imaging of Alzheimer's disease. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.138

文献信息

• One-Pot Synthesis of 2-Aryl- and 2-Alkylbenzothiazoles under Microwave Irradiation
  作者：Edward R. Biehl、Sukanta Kamila、Hongming Zhang

  DOI：10.3987/com-05-10466

  日期：——

  Eco-friendly direct solvent-free reactions of o-aminothiophenol and aromatic or aliphatic β-keto esters with microwave irradiation produced 2-substituted benzothiazoles in excellent yield. Experiments that compared microwave irradiation to conventional heating methods showed that the former gives the 2-substituted benzothiazoles faster and in higher yields. The formation of the titled compounds probably

  邻氨基苯硫酚和芳香族或脂肪族 β-酮酯在微波辐射下的环保直接无溶剂反应以优异的产率产生 2-取代的苯并噻唑。将微波辐射与传统加热方法进行比较的实验表明，前者更快地产生 2-取代的苯并噻唑，产率更高。标题化合物的形成可能涉及将硫醇基团亲核加成到 β-酮酯的酮基上，随后从所得加合物中消除乙酸乙酯。然后加合物经历邻氨基与羰基的分子内加成，得到加合物，从加合物中除去水，得到2-取代的苯并噻唑。
• Nickel-Catalyzed CH Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules
  作者：Takuya Yamamoto、Kei Muto、Masato Komiyama、Jérôme Canivet、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1002/chem.201101091

  日期：2011.8.29

  Novel nickel‐based catalytic systems for the CH arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)2/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)2/dppf (dppf=1,1′‐bis

  对于C新颖的镍基催化体系与卤代芳烃和芳基三氟甲磺酸酯唑h的芳基化得到了发展。我们已经确定，Ni（OAc）2 / bipy / LiO t Bu用作与芳基溴化物和碘化物作为芳基亲电子试剂偶联的一般催化体系。对于与更具挑战性的亲电试剂（例如芳基氯化物和三氟甲磺酸酯）偶联，发现Ni（OAc）2 / dppf（dppf = 1,1'-bis（diphenylphosphino）ferrocene）系统是有效的。噻唑，苯并噻唑，恶唑，苯并恶唑和苯并咪唑可用作杂芳烃偶联伴侣。经过进一步研究，我们发现了使用Mg（O t Bu）2进行本偶联的新方案作为LiO t Bu的温和且便宜的替代品。还描述了试图揭示这种镍催化的杂联芳基偶联机理的尝试。该新开发的方法已成功应用于非布索坦（一种有效治疗痛风和高尿酸血症的黄嘌呤氧化酶抑制剂），他法米第（一种有效治疗TTR淀粉样蛋白多神经病的药物）和texaline（一种天然的抗结核药物）的合成活动）。
• Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates
  作者：Jérôme Canivet、Junichiro Yamaguchi、Ikuya Ban、Kenichiro Itami

  DOI：10.1021/ol9001587

  日期：2009.4.16

  Ni-based catalytic systems for the arylation of heteroarenes with aryl halides and triflates have been established. Ni(OAc)2/bipy is a general catalyst for aryl bromides/iodides, and Ni(OAc)2/dppf is effective for aryl chlorides/triflates. Thiazole, benzothiazole, oxazole, benzoxazole, and benzimidazole are applicable as heteroarene coupling partners. A rapid synthesis of febuxostat, a drug for gout

  已经建立了镍基催化体系，用于杂芳烃与芳基卤化物和三氟甲磺酸酯的芳基化。Ni（OAc）2 / bipy是芳基溴化物/碘化物的常规催化剂，Ni（OAc）2 / dppf对于芳基氯化物/三氟甲磺酸酯有效。噻唑，苯并噻唑，恶唑，苯并恶唑和苯并咪唑可用作杂芳烃偶联伙伴。还显示了快速合成非布索坦（一种用于痛风和高尿酸血症的药物）。
• Efficient synthesis of benzothiazole derivatives by reaction of bis(2-aminophenyl) disulfides with aldehydes mediated by NaSH under microwave irradiation
  作者：Lei Liu、Fa Zhang、Hongliang Wang、Ning Zhu、Bo Liu、Hailong Hong、Limin Han

  DOI：10.1080/10426507.2016.1259227

  日期：2017.4.3

  ABSTRACT 2-Substituted benzothiazoles were synthesized through condensation of bis(2-aminophenyl) disulfides with arylaldehydes catalyzed by inexpensive NaSH in PEG-300 and assisted by low energy microwave irradiation(25 W). Various 2-substitutedbenzothiazoles were obtained in moderate to high yields after simple post-reaction processing including adding distilled water, filtrating, and drying. Moreover,

  图形摘要 摘要 2-取代的苯并噻唑是通过双（2-氨基苯基）二硫化物与芳醛缩合合成的，由 PEG-300 中的廉价 NaSH 催化，并辅以低能微波辐射 (25 W)。经过简单的后反应处理，包括加入蒸馏水、过滤和干燥，以中等至高产率获得了各种 2-取代苯并噻唑。此外，发现二硫键的 SS 键被 NaSH 和中间体苯并噻唑啉还原。
• Novel synthesis of benzothiazole by self-redox tandem reaction of disulfide with aldehyde
  作者：Bo Liu、Ning Zhu、Hailong Hong、Limin Han

  DOI：10.1016/j.tet.2015.10.029

  日期：2015.12

  A novel methodology for the preparation of benzothiazole derivatives via the reaction of ortho-anilino disulfides with aryl and heteroaryl aldehydes catalyzed by Na2S·9H2O has been developed. The reaction mechanism was investigated by LC–MS and 1H NMR. The disulfide was cleaved firstly by the interchange reaction of the disulfide and metal sulfide, and the resulting thiol reacted in situ with the aldehyde

  经由反应一种新颖的方法用于苯并噻唑衍生物的制备邻-苯胺基二硫化物与芳基和杂芳基醛催化的Na 2 S·9H 2 O具有被开发出来。的反应机理，通过LC-MS和研究1 1 H NMR。二硫化物由二硫化物和金属硫化物的交换反应首先切割，将所得的硫醇就地反应的与醛以形成相应的苯并噻唑啉。随后，将中间体苯并噻唑啉减少二硫化物到巯基和它被氧化为苯并噻唑。过量的苯并噻唑啉通过空气氧化，二硫化物的两半被最终转化为所需的苯并噻唑。