2-(benzylsulfanyl)-5-chloro-1,3-benzothiazole | 92161-73-4

• 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: 2-(benzylsulfanyl)-5-chloro-1,3-benzothiazole
• 英文别名: 2-(benzylthio)-5-chlorobenzo[d]thiazole；2-benzylmercapto-5-chloro-benzothiazole；2-Benzylmercapto-5-chlor-benzothiazol；2-Benzylsulfanyl-5-chloro-1,3-benzothiazole
• CAS: 92161-73-4
• 化学式: C₁₄H₁₀ClNS₂
• 分子量: 291.825
• InChiKey: IQZCJHUDJDBFNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzylsulfanyl)-5-chloro-1,3-benzothiazole 在 碘 作用下， 生成 3-benzyl-5-chloro-3H-benzothiazole-2-thione
  参考文献：
  名称：

  Reed et al., Journal of the Chemical Society, 1939, p. 473,475

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯苯并噻唑 、 benzyl thiosulphate 在 copper diacetate 、 silver nitrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以80%的产率得到2-(benzylsulfanyl)-5-chloro-1,3-benzothiazole
  参考文献：
  名称：

  Ag–Cu copromoted direct C2–H bond thiolation of azoles with Bunte salts as sulfur sources

  摘要：

  使用铜盐和银盐的共同作用，实现了与Bunte盐的直接C2-H硫化作用，在中等到良好的产率下提供了各种取代的2-硫代咪唑。

  DOI：

  10.1039/d1ob00823d

文献信息

• The toxicity of organic sulphides to the eggs and larvae of the glasshouse red spider mite. vii.—Benzyl phenyl sulphides (α-substituted)
  作者：J. E. Cranham、D. Greenwood、H. A. Stevenson

  DOI：10.1002/jsfa.2740090305

  日期：1958.3

  The synthesis of a number of benzyl phenyl sulphides, substituted in the α-position of the benzyl moiety, is described and their toxicities to the eggs and young mites of the glasshouse red spider (Tetranychus telarius L.) are tabulated.

  描述了许多苄基部分的 α 位取代的苄基苯基硫化物的合成，并列出了它们对温室红蜘蛛（Tetranychus telarius L.）的卵和幼螨的毒性。
• Easy S-Alkylation of Arylthioureas and 2-Mercaptobenzothiazoles Using Tetraalkylammonium Salts under Transition-Metal-Free Conditions
  作者：Xiao-Hu Xu、Er-Jun Hao、Zhen Shi、Zhi-Bing Dong

  DOI：10.1021/acs.joc.2c00728

  日期：2022.8.5

  A highly-efficient and practical method for S-alkylation of arylthioureas was reported. Using tetraalkylammonium salts as alkylation reagents, a series of 68 S-substituted aryl-isothioureas were obtained in good to excellent yields under transition-metal-free conditions. The protocol features simple performance, broad functional group tolerance, good to excellent yields, and easily available starting

  报道了一种高效实用的芳基硫脲S-烷基化方法。使用四烷基铵盐作为烷基化试剂，在无过渡金属条件下以良好至优异的收率获得了一系列 68 S-取代的芳基异硫脲。该协议具有简单的性能、广泛的官能团耐受性、良好的产量以及易于获得的起始材料，显示出制备多种生物或药物活性化合物的潜在合成价值。
• Thiazole Orange derivatives: Synthesis, fluorescence properties, and labeling cancer cells
  作者：Xuening Fei、Yingchun Gu、Ying Ban、Zhijun Liu、Baolian Zhang

  DOI：10.1016/j.bmc.2008.11.083

  日期：2009.1

  A series of Thiazole Orange (TO) derivatives were synthesized and modified by introducing different substitutional groups on benzothiazole and 4-methylquinoline All the TO derivatives were confirmed by (HNMR)-H-1 and MS. TO derivative bearing NH2- was modified by folic acid and used to label breast cancer cells. The phenomenon of fluorescence enhancement was shown by the fluorescence spectrums of TO derivatives and micrographs of the labeled breast cancer cells. It offered a new try in the aspect of labeling cells by the embedded dyes. (C) 2008 Elsevier Ltd. All rights reserved.
• Ag–Cu copromoted direct C2–H bond thiolation of azoles with Bunte salts as sulfur sources
  作者：Rui Wang、Hongyan Xu、Ying Zhang、Yuntao Hu、Yingsu Wei、Xiao Du、Huaiqing Zhao

  DOI：10.1039/d1ob00823d

  日期：——

  A direct C2–H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts, furnishing various substituted 2-thioazoles in moderate to good yields.

  使用铜盐和银盐的共同作用，实现了与Bunte盐的直接C2-H硫化作用，在中等到良好的产率下提供了各种取代的2-硫代咪唑。
• Reed et al., Journal of the Chemical Society, 1939, p. 473,475
  作者：Reed et al.

  DOI：——

  日期：——