(6-methylbenzo[d]thiazol-2-yl)(p-tolyl)methanone | 1268700-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6-methylbenzo[d]thiazol-2-yl)(p-tolyl)methanone
• 英文别名: 6-methyl-2-(4-methylbenzoyl)benzothiazole；(6-Methyl-1,3-benzothiazol-2-yl)-(4-methylphenyl)methanone；(6-methyl-1,3-benzothiazol-2-yl)-(4-methylphenyl)methanone
• CAS: 1268700-08-8
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: SYJDLQHNKQFPAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2,2-二溴乙烯)-4-甲基苯 在 ruthenium trichloride 、 四丁基氟化铵 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (6-methylbenzo[d]thiazol-2-yl)(p-tolyl)methanone
  参考文献：
  名称：

  Synthesis of heteroaryl ketones via tandem reaction of 1,1-dibromoethenes

  摘要：

  A novel method for the synthesis of heteroaryl ketones through one-pot tandem reaction of 1,1-dibromoethenes with 2-amino(thio)phenols promoted by TBAF center dot 3H(2)O and RuCl3(5%)/air was developed. This novel method includes several reactions in one-pot and utilizes economical yet efficient reagents to generate synthetically and biologically interesting heteroaryl ketones under mild conditions with good efficiency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.111

文献信息

• RuCl3·3H2O Catalyzed Tandem Reaction of Alkynylbromides with 2-Aminothiophenols in Water: A Convenient Synthesis of 2-Benzoylbenzothiazoles
  作者：Xuesen Fan、Yan He、Shenghai Guo、Xinying Zhang

  DOI：10.1071/ch11217

  日期：——

  RuCl3·3H2O catalyzed tandem reaction of alkynyl bromides with 2-aminothiophenols mediated by water is shown to represent a convenient synthesis of 2-benzoylbenzothiazoles. In addition, the Ru(iii) catalyst could be readily recovered and efficiently reused together with water up to three times.

  RuCl 3 ·3H 2 O催化炔基溴与水介导的2-氨基硫酚的串联反应表明可以方便地合成2-苯甲酰基苯并噻唑。另外，Ru（iii）催化剂可以容易地回收并与水一起有效地重复使用多达三遍。
• A Sustainable Synthesis of 2-Benzoxazyl and 2-Benzothiazyl Ketones from Alkynyl Bromides and 2-Amino(thio)phenols Promoted by a Recyclable Catalytic System
  作者：Liangyan Cui、Yan He、Xuesen Fan

  DOI：10.1002/cjoc.201100472

  日期：2012.4

  An environmentally and economically sustainable synthesis of 2‐benzoxazyl ketones and 2‐benzothiazyl ketones through FeCl3·6H2O catalyzed tandem reactions of alkynyl bromides with 2‐amino(thio)phenols in [bmim]BF4 has been developed. Remarkable advantages of this new synthetic strategy include high efficiency, readily available starting materials, and recyclable catalyst and reaction medium.

  通过FeCl 3 ·6H 2 O催化炔基溴化物与2-氨基（硫代）苯酚在[bmim] BF 4中的串联反应，在环境和经济上可持续地合成2-苯并恶唑酮和2-苯并噻唑酮。这种新的合成策略的显着优势包括高效，易于获得的原料以及可循环使用的催化剂和反应介质。
• A Novel Self-Sequence Reaction Network Involving a Set of Six Reactions in One Pot: The Synthesis of Substituted Benzothiazoles from Aromatic Ketones and Anilines
  作者：Wei-Jian Xue、Ya-Qiong Guo、Fang-Fang Gao、Hong-Zheng Li、An-Xin Wu

  DOI：10.1021/ol400029t

  日期：2013.2.15

  and readily available aromatic ketones and anilines as starting materials resulted in the construction of 2-acylbenzothiazoles via a novel self-sequence reaction network, which assembles six reactions in one pot. The reaction network not only supplied a novel method for constructing complex molecules but also provided a typical example for logical self-organization synthesis.

  使用简单易得的芳香族酮和苯胺作为起始原料，可以通过一个新颖的自序反应网络构建2-酰基苯并噻唑，该网络在一个罐中组装六个反应。该反应网络不仅为构建复杂分子提供了一种新颖的方法，而且为逻辑自组织合成提供了一个典型的例子。
• An Efficient Copper-Mediated Route for the Synthesis of 2-Substituted Benzothiazoles from Dithioesters and Investigation of Their Antibacterial Activities
  作者：Maralinganadoddi P. Sadashiva、Kodipura P. Sukrutha、Kuppalli R. Kiran、Kodagahally T. Gunashree、Shivakumar Divyashree、Prerana Purusotham、Marikunte Y. Sreenivasa

  DOI：10.1055/a-2193-5436

  日期：2024.2

  one-pot synthesis of 2-aryl/2-aroylbenzothiazoles through copper-mediated condensation of 2-chloroanilines with dithioesters has been developed. The method provides good isolated yields and exhibits broad functional group tolerance, accommodating both electron-donating and electron-withdrawing groups on the substrates. A series of synthesized compounds was evaluated for their antibacterial activity against

  通过铜介导的 2-氯苯胺与二硫酯的缩合，开发出了一种有效的一锅法合成 2-芳基/2-芳酰基苯并噻唑的方法。该方法提供了良好的分离产率，并表现出广泛的官能团耐受性，可容纳底物上的给电子基团和吸电子基团。评估了一系列合成化合物对肺炎克雷伯菌、铜绿假单胞菌和副伤寒沙门氏菌的抗菌活性。在该系列中，三种化合物对所测试的病原体表现出显着的抑制作用，其中一种还在琼脂井扩散测定和肉汤微量稀释测定中显示出作为有效化合物的潜力。此外，在结晶紫测定和MTT测定中，这三种化合物在浓度为10 mM时对病原体生物膜的形成表现出强烈的抑制作用。这些发现凸显了这些化合物具有前景的抗菌和抗生物膜特性，表明它们作为针对所测试病原体的潜在治疗剂进行进一步研究的潜力。
• A novel and practical synthesis of 2-benzoylbenzothiazoles and 2-benzylbenzothiazoles
  作者：Xuesen Fan、Yan He、Yangyang Wang、Zaikun Xue、Xinying Zhang、Jianji Wang

  DOI：10.1016/j.tetlet.2010.12.057

  日期：2011.2

  A novel methodology for the synthesis of 2-benzoylbenzothiazoles and 2-benzylbenzothiazoles through FeCl3 center dot 6H(2)O catalyzed, air oxidized tandem process from commercially available 2-aminothiophenols and phenylacetaldehydes by using an ionic liquid as both reaction medium and co-catalyst was developed. (C) 2011 Elsevier Ltd. All rights reserved.