6-methyl-2-(p-tolyl)benzo[d]thiazole | 65490-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-methyl-2-(p-tolyl)benzo[d]thiazole
• 英文别名: 6-Methyl-2-(4-methylphenyl)-1,3-benzothiazole
• CAS: 65490-80-4
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: GBADUFXUHMBFAW-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C(Solv: ethanol (64-17-5))
• 沸点：
  383.5±45.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-2-(p-tolyl)benzo[d]thiazole 、 N-溴代丁二酰亚胺(NBS) 生成 2-<4-(bromomethyl)phenyl>-6-methylbenzothiazole
  参考文献：
  名称：

  YOSHINO, KOHICHIRO;KOHNO, TOSHIHIKO;UNO, TOSHIO;TOMINORI, MORITA;TSUKAMOT+, J. MED. CHEM., 1986, 29, N 5, 820-825

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-methylbenzylidene)-4-methylaniline N-oxide 在 苯基硫代膦酰二氯 作用下， 生成 6-methyl-2-(p-tolyl)benzo[d]thiazole
  参考文献：
  名称：

  Nagase,R. et al., Heterocycles, 1977, vol. 8, p. 243 - 246

  摘要：

  DOI：

文献信息

• Metal-Free Synthesis of 2-Arylbenzothiazoles from Aldehydes, Amines, and Thiocyanate
  作者：Amrita Dey、Alakananda Hajra

  DOI：10.1021/acs.orglett.9b00245

  日期：2019.3.15

  A highly efficient method for the synthesis of 2-arylbenzothiazoles has been developed using readily available aromatic amines, benzaldehydes, and NH4SCN as a sulfur source. A library of 2-arylbenzothiazoles with wide functional group compatibility has been synthesized in good yields through iodine-mediated oxidative annulation.

  已经开发了一种高效的合成2-芳基苯并噻唑的方法，该方法使用容易获得的芳族胺，苯甲醛和NH 4 SCN作为硫源。通过碘介导的氧化环化反应，以高收率合成了具有广泛官能团相容性的2-芳基苯并噻唑文库。
• Iron-Promoted Three-Component 2-Substituted Benzothiazole Formation via Nitroarene <i>ortho</i>-C–H Sulfuration with Elemental Sulfur
  作者：Qiaoyan Xing、Yanfeng Ma、Hao Xie、Fuhong Xiao、Feng Zhang、Guo-Jun Deng

  DOI：10.1021/acs.joc.8b02619

  日期：2019.2.1

  A three-component procedure for the preparation of 2-substituted benzothiazoles from nitroarenes, alcohols, and sulfur powder is described. The reaction showed a good functional group tolerance to provide the heterocyclic products in moderate to good yields. The sequential assembly involving nitro reduction, C–N condensation, and C–S bond formation has been realized in one pot.

  描述了一种由硝基芳烃，醇和硫粉制备2-取代的苯并噻唑的三组分方法。该反应显示出良好的官能团耐受性，以中等至良好的产率提供了杂环产物。在一个罐中就实现了包括硝基还原，C–N缩合和C–S键形成的顺序组装。
• Copper-catalyzed solvent-free redox condensation of benzothiazoles with aldehydes or benzylic alcohols
  作者：Mingliang Zhang、Wen-Ting Lu、Wenqing Ruan、Hui-Jun Zhang、Ting-Bin Wen

  DOI：10.1016/j.tetlet.2014.01.120

  日期：2014.3

  2-aryl- and 2-alkyl-substituted benzothiazoles via a copper-catalyzed redox condensation process between benzothiazoles and aldehydes or benzylic alcohols has been developed. The reaction proceeded under mild reaction conditions using environmentally benign tert-butyl hydroperoxide (TBHP) as the oxidant. A reaction mechanism involving the ring-opening of benzothiazoles initiated by the attack of acyl

  已经开发了通过苯并噻唑与醛或苯甲醇之间的铜催化的氧化还原缩合工艺来构建2-芳基-和2-烷基取代的苯并噻唑的有效且实用的方法。反应在温和的反应条件下进行，使用环境友好的叔丁基氢过氧化物（TBHP）作为氧化剂。提出了一种基于苯甲酰二硫化物中间体的分离反应机理，该反应机理涉及通过酰基自由基侵袭噻唑环和分子内缩合引发苯并噻唑的开环。
• Development of (quinolinyl)amido-based pincer palladium complexes: a robust and phosphine-free catalyst system for C–H arylation of benzothiazoles
  作者：Hanumanprasad Pandiri、Vineeta Soni、Rajesh G. Gonnade、Benudhar Punji

  DOI：10.1039/c7nj00452d

  日期：——

  (Quinolinyl)amido-ligated palladium(II) complexes have been synthesized and applied in the catalytic C–H bond arylation of benzothiazoles. The tridentate ligand precursors R2N-C(O)CH2-(NH)-C9H6N [(R2NNN8-Q)–H; R2N = morpholinyl, Me-N-piperazinyl] and the pincer palladium complexes [κN,κN,κN-R2N-C(O)CH2-(μ-N)-C9H6N}]PdX [(R2NNN8-Q)PdX R2N = Et2N, morpholinyl, Me-N-piperazinyl; X = OAc or Cl}] were

  （喹啉基）氨基连接的钯（II）配合物已经合成，并用于苯并噻唑的催化C–H键芳基化。三齿配体前体R 2 N-C（O）CH 2-（NH）-C 9 H 6 N [（R2 NNN 8-Q）–H; [R 2 N =吗啉基，ME- Ñ哌嗪基]和钳形钯络合物[κ Ñ，κ Ñ，κ ñ - R 2 N-C（O）CH 2 - （μ-N）-C 9 ħ 6 N}] PdX [（R2 NNN 8-Q）PdX R 2 N = Et2 N，吗啉基，Me- N-哌嗪基；X = OAc或Cl}]被有效地合成，并通过各种分析技术进行表征。通过用KI处理复合物（ Et2 NNN 8-Q）PdCl，可以以优异的收率获得碘衍生物（ Et2 NNN 8-Q）PdI。通过X射线晶体学阐明了（ Et2 NNN 8-Q）Pd（OAc）（ 2a），（ Et2 NNN 8-Q）PdCl（ 3a）和（ Et2 NNN 8-Q）PdI（ 4a）的分子结构。
• Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization
  作者：Masahiro Teramoto、Takumi Mizuno、Mitsutaka Imoto、Motonori Takeda、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1055/s-0041-1737760

  日期：2022.3

  synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to

  开发了一种基于氧化还原环化的可持续先进合成方法，用于在不使用过渡金属催化剂的情况下从现成的硝基苯、苄胺和元素硫合成 2-芳基苯并噻唑，收率良好。这种方法非常显着：硝基还原、苄胺氧化还原反应、硫化、缩合和环化，都在一个步骤中进行，生成杂环。它也是高度原子经济的，不需要任何外部氧化剂或还原剂。