2-(2-methoxyphenylthio)benzo[d]thiazole | 1032690-57-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(2-methoxyphenylthio)benzo[d]thiazole
• 英文别名: 2-(2-Methoxyphenyl)sulfanyl-1,3-benzothiazole；2-(2-methoxyphenyl)sulfanyl-1,3-benzothiazole
• CAS: 1032690-57-5
• 化学式: C₁₄H₁₁NOS₂
• 分子量: 273.379
• InChiKey: XTJLASZDGWEEMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Methoxyphenylmagnesium bromide 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 nickel dichloride 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 2.83h， 生成 2-(2-methoxyphenylthio)benzo[d]thiazole
  参考文献：
  名称：

  有机丙烷试剂与 2-巯基苯并 5 元杂环的交叉偶联反应有效合成苯并 5 元杂环硫化物

  摘要：

  通过 2-巯基苯并 5 元杂环与（杂）芳基铝试剂的交叉偶联反应，开发了一种高效且简单的合成苯并 5 元杂环硫化物的路线。在温和的反应条件下，可以以 32-87% 的分离产率获得各种苯并 5 元杂环硫化物衍生物。在 2-巯基苯并 5-元杂环中带有给电子或吸电子基团的芳基以 40-78% 的分离产率得到产物。广泛的底物范围和克级高效的典型维护使该协议成为合成苯并 5 元杂环硫化物衍生物的潜在实用方法。根据实验结果，提出了一种可能的催化循环。

  DOI：

  10.1016/j.tet.2021.132564

文献信息

• Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water
  作者：Xing Liu、Shi-Bo Zhang、Hui Zhu、Zhi-Bing Dong

  DOI：10.1021/acs.joc.8b01644

  日期：2018.10.5

  efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-

  已经开发了用于制备2-芳基硫代苯并噻唑的有效串联方法。通过2-氨基苯硫醇与四甲基秋兰姆二硫化物（TMTD）的缩合，原位生成2-巯基苯并噻唑，其随后与碘代苯偶合，以单锅方式流畅地得到所需的2-芳基硫代苯并噻唑。该方法也可用于合成2-芳基硫代苯并恶唑。廉价的金属催化剂和配体，温和的反应温度以及水作为溶剂，使该方案在有机合成中具有实用价值和实用性。
• The Direct Thiolation of Benzothiazole Catalyzed by Copper Complex in Superbase System
  作者：Yu Yuan、Xiaowei Wang、Yanjun Li

  DOI：10.1055/s-0032-1316891

  日期：——

  The copper-catalyzed direct thiolation of benzothiazole with iodobenzene and sulfur in superbase system under oxygen atmosphere is reported. The corresponding 2-thio-substituted benzothiazoles were formed in satisfactory yields.
• Copper Oxide Nanoparticle-Catalyzed Chalcogenation of the Carbon-Hydrogen Bond in Thiazoles: Synthesis of 2-(Organochalcogen)thiazoles
  作者：Alisson R. Rosario、Kamila K. Casola、Carla E. S. Oliveira、Gilson Zeni

  DOI：10.1002/adsc.201300497

  日期：2013.10.11

  AbstractWe present (homepage: www.ufsm.br) herein the application of copper nanoparticles/diorganyl dichalcogenides to promote the synthesis of 2‐(organochalcogen)thiazoles via direct carbon‐hydrogen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron‐donating and electron‐withdrawing substituents, in the aromatic ring bonded to the chalcogen atom of diorganyl dichalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.magnified image
• Novel copper/PEG-400 catalyst systems for chemoselective S- and N-arylation of 2-mercaptobenzothiazole
  作者：Xiaokang Li、Tangjun Yuan、Yu Yang、Junmin Chen

  DOI：10.1016/j.tet.2014.10.075

  日期：2014.12

  A novel approach for chemoselective S- and N-arylation of 2-mercaptobenzothiazole was developed by copper/PEG-400 catalyst systems. Copper source and reaction temperature play an important role in this protocol, selective S-arylation of 2-mercaptobenzothiazole was achieved by using CuI/PEG-400/50 degrees C catalyst system, while selective N-arylation was achieved with CuO/PEG-400/140 degrees C catalyst system. Both are compatible with a variety of aryl halides and selectively give the desired S- and N-arylation products in good to excellent yields, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
• Iron-Catalyzed S-Arylation of Thiols with Aryl Iodides
  作者：Arkaitz Correa、Mónica Carril、Carsten Bolm

  DOI：10.1002/anie.200705668

  日期：2008.3.31