4-nitro-6-(trifluoromethyl)benzotrithiole | 70001-71-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-nitro-6-(trifluoromethyl)benzotrithiole
• 英文别名: 4-nitro-6-(trifluoromethyl)-1,2,3-benzotrithiole；4-nitro-6-(trifluoromethyl)-benzo[d][1,2,3]trithiole；4-Nitro-6-trifluoromethyl-1,2,3-benzotrithiole
• CAS: 70001-71-7
• 化学式: C₇H₂F₃NO₂S₃
• 分子量: 285.292
• InChiKey: UYXICFIAIIYSNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-nitro-6-(trifluoromethyl)benzotrithiole 在 sodium hydrogen sulfide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 8-(trifluoromethyl)benzo[f][1,2,3,4,5]pentathiepin-6-amine
  参考文献：
  名称：

  Synthesis of 6-Aminobenzopentathiepines by Reactions of 4-Nitrobenzodithiol- 2-ones with NaHS

  摘要：

  含有4- nitro基的苯二硫酮与NaHS反应，生成了6-氨基苯五硫啶和4-硝基苯三硫醇的混合物。产物的比例和产率取决于芳香环中的取代基。根据苯五硫啶的产率，可以推断出以下取代基效能的系列：CF3 > F > Cl > CN。氨基苯五硫啶可能是通过中间体苯三硫醇形成的；该转化显然是从硝基的还原开始的。

  DOI：

  10.2174/157017811795038331
• 作为产物：
  描述：

  S-[2-[[2-(dimethylcarbamoylsulfanyl)-3-nitro-5-(trifluoromethyl)phenyl]disulfanyl]-6-nitro-4-(trifluoromethyl)phenyl] N,N-dimethylcarbamothioate 在 sodium hydroxide 、 sodium hydrogensulfide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 生成 4-nitro-6-(trifluoromethyl)benzotrithiole
  参考文献：
  名称：

  Reactions of S,S'-[2,2'-dithiobis(nitrophenyl)] bis(N,N-dimethylcarbamothioates) with hydroxide and hydrosulfide anions. A synthesis of nitrobenzotrithioles

  摘要：

  DOI：

  10.1021/jo01311a063

文献信息

• Synthesis of benzopentathiepin analogs and their evaluation as inhibitors of the phosphatase STEP
  作者：Tyler D. Baguley、Angus C. Nairn、Paul J. Lombroso、Jonathan A. Ellman

  DOI：10.1016/j.bmcl.2015.01.020

  日期：2015.3

  Striatal-enriched protein tyrosine phosphatase (STEP) is a brain specific protein tyrosine phosphatase that has been implicated in many neurodegenerative diseases, such as Alzheimer's disease. We recently reported the benzopentathiepin TC-2153 as a potent inhibitor of STEP in vitro, cells and animals. Herein, we report the synthesis and evaluation of TC-2153 analogs in order to define what structural features are important for inhibition and to identify positions tolerant of substitution for further study. The trifluoromethyl substitution is beneficial for inhibitor potency, and the amine is tolerant of acylation, and thus provides a convenient handle for introducing additional functionality such as reporter groups. (C) 2015 Elsevier Ltd. All rights reserved.
• Cytotoxic and cancer preventive activity of benzotrithioles and benzotrithiole oxides, synthetic analogues of varacins
  作者：Alexandra S. Kuzmich、Tatyana M. Khomenko、Sergey N. Fedorov、Tatyana N. Makarieva、Larisa K. Shubina、Nina I. Komarova、Dina V. Korchagina、Tatyana V. Rybalova、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1007/s00044-016-1759-8

  日期：2017.2

  The cytotoxic and cancer preventive activities of synthetic analogs of natural varacins with polysulfide groups were studied. Presence of a sulfoxide group was found to have no significant effect on the cytotoxicity of these compounds. At the same time, this group is important for inhibition of colony formation of tumor cells treated with tumor promoter thus demonstrating cancer preventive activity. The most promising compound appears to be a synthetic varacin C analog, sulfoxide 10a, which exhibits the cancer preventive activity at dose into 100 times lower than its cytotoxic concentrations.
• RASHEED K.; WARKENTIN J. D., J. ORG. CHEM., 1980, 45, NO 23, 4806-4807
  作者：RASHEED K.、 WARKENTIN J. D.

  DOI：——

  日期：——
• Asymmetric oxidation of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole
  作者：T. M. Khomenko、D. V. Korchagina、K. P. Volcho、N. F. Salakhutdinov

  DOI：10.1134/s1070428009090140

  日期：2009.9

  Both enantiomers of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole 1-oxide as analogs of Varacins B and C were synthesized for the first time. The use of the Modena method ensures higher optical purity but lower yields of the chiral sulfoxides, as compared to the Kagan procedure.
• Synthesis of 6-Aminobenzopentathiepines by Reactions of 4-Nitrobenzodithiol- 2-ones with NaHS
  作者：Tatyana M. Khomenko、Dina V. Korchagina、Nina I. Komarova、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.2174/157017811795038331

  日期：2011.3.1

  The reactions of benzodithiol-2-ones containing a 4-nitro group with NaHS led to mixtures of 6- aminobenzopentathiepines and 4-nitrobenzotrithiols. The product ratio and yields depend on the substituent in the aromatic ring. Based on the yields of benzopentathiepines, the following series of substituent efficiency can be inferred: CF3 F, Cl CN. Aminobenzopentathiepines are probably formed via the intermediate benzotrithiols; the transformation apparently starts with the reduction of the nitro group.

  含有4- nitro基的苯二硫酮与NaHS反应，生成了6-氨基苯五硫啶和4-硝基苯三硫醇的混合物。产物的比例和产率取决于芳香环中的取代基。根据苯五硫啶的产率，可以推断出以下取代基效能的系列：CF3 > F > Cl > CN。氨基苯五硫啶可能是通过中间体苯三硫醇形成的；该转化显然是从硝基的还原开始的。