5-甲基-5H-二苯并[B,D]噻吩-5-三氟甲烷磺酸盐 | 112359-25-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 5-甲基-5H-二苯并[B,D]噻吩-5-三氟甲烷磺酸盐
• 英文名称: S-methyl dibenzothiophenium triflate
• 英文别名: 5-Methyl-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate；5-methyldibenzothiophen-5-ium;trifluoromethanesulfonate
• CAS: 112359-25-8
• 化学式: CF₃O₃S*C₁₃H₁₁S
• 分子量: 348.367
• InChiKey: ROHWBLNJJVPWCN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P501,P260,P270,P264,P280,P303+P361+P353,P301+P330+P331,P363,P301+P312+P330,P304+P340+P310,P305+P351+P338+P310,P405
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H314
• 包装等级：
  III
• 储存条件：
  存储条件为：2-8°C，避光，惰性气体环境。

反应信息

• 作为反应物：
  描述：

  5-甲基-5H-二苯并[B,D]噻吩-5-三氟甲烷磺酸盐 在 吡啶 、 水 作用下， 反应 0.17h， 以90%的产率得到二苯并噻吩
  参考文献：
  名称：

  Dibenzothienobisbenzothiophene-a novel fused-ring oligomer with high field-effect mobility

  摘要：

  具有刚性熔环结构的共轭低聚物对有机场效应晶体管很有意义，在这种晶体管中，相邻分子之间需要有很强的π-π相互作用，以获得很高的电荷载流子迁移率。二苯并[b,b′]噻吩并[2,3-f:5,4-f′]双[1]苯并噻吩（DBTBT）是通过一种新路线合成的，其关键步骤是芳香族甲基硫醚的酸诱导分子内环化反应。采用真空升华法沉积的多晶 DBTBT 薄膜场效应晶体管（FET）显示出 0.15 cm 2 (Vs) -1 的高场效应迁移率和大于 10 6 的导通-关断电流比。耦合反应不具有区域选择性，而且已经发现了不同的区域异构体。当升华薄膜含有不同异构体的混合物时，场效应晶体管的性能会下降。

  DOI：

  10.1039/a902679g
• 作为产物：
  描述：

  2-溴联苯 在 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 63.0h， 生成 5-甲基-5H-二苯并[B,D]噻吩-5-三氟甲烷磺酸盐
  参考文献：
  名称：

  Dibenzothienobisbenzothiophene-a novel fused-ring oligomer with high field-effect mobility

  摘要：

  具有刚性熔环结构的共轭低聚物对有机场效应晶体管很有意义，在这种晶体管中，相邻分子之间需要有很强的π-π相互作用，以获得很高的电荷载流子迁移率。二苯并[b,b′]噻吩并[2,3-f:5,4-f′]双[1]苯并噻吩（DBTBT）是通过一种新路线合成的，其关键步骤是芳香族甲基硫醚的酸诱导分子内环化反应。采用真空升华法沉积的多晶 DBTBT 薄膜场效应晶体管（FET）显示出 0.15 cm 2 (Vs) -1 的高场效应迁移率和大于 10 6 的导通-关断电流比。耦合反应不具有区域选择性，而且已经发现了不同的区域异构体。当升华薄膜含有不同异构体的混合物时，场效应晶体管的性能会下降。

  DOI：

  10.1039/a902679g
• 作为试剂：
  描述：

  methyl (1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18-dihydroxy-32,35,37,48-tetramethoxy-19-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylate 在 四羟基二硼 、 potassium acetate 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 、 铜 、 碳酸氢钠 、 5-甲基-5H-二苯并[B,D]噻吩-5-三氟甲烷磺酸盐 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Probing the Role of the Vancomycin E-Ring Aryl Chloride: Selective Divergent Synthesis and Evaluation of Alternatively Substituted E-Ring Analogues

  摘要：

  The selective functionalization of vancomycin aglycon derivatives through conversion of the E-ring aryl chloride to a reactive boronic acid and its use in the synthesis of a systematic series of vancomycin E-ring analogues are described. The series was used to examine the E-ring chloride impact in binding D-Ala-D-Ala and on antimicrobial activity. In contrast to the reduced activity of the unsubstituted E-ring derivatives, hydrophobic and relatively nonpolar substituents approach or match the chloro-substituted vancomycin and were insensitive to the electronic character of the substituent (e.g., Cl vs CN/OMe), whereas highly polar substituents fail to provide the enhancements. Moreover, the active permethylated vancomycin aglycon derivatives exhibit VanB VRE antimicrobial activity at levels that approach (typically within 2-fold) their activity against sensitive bacteria. The robust borylation reaction also enabled the functionalization of a minimally protected vancomycin aglycon (N-Boc-vancomycin aglycon) and provides a direct method for the preparation of previously inaccessible analogues.

  DOI：

  10.1021/jm4004494

文献信息

• Sulfonium Salts as Alkylating Agents for Palladium-Catalyzed Direct Ortho Alkylation of Anilides and Aromatic Ureas
  作者：Dániel Cs. Simkó、Péter Elekes、Vivien Pázmándi、Zoltán Novák

  DOI：10.1021/acs.orglett.7b03813

  日期：2018.2.2

  novel method for the ortho alkylation of acetanilide and aromatic urea derivatives via C–H activation was developed. Alkyl dibenzothiophenium salts are considered to be new reagents for the palladium-catalyzed C–H activation reaction, which enables the transfer of methyl and other alkyl groups from the sulfonium salt to the aniline derivatives under mild catalytic conditions.

  开发了一种通过C–H活化对乙酰苯胺和芳香族脲衍生物进行邻位烷基化的新方法。烷基二苯并噻吩鎓盐被认为是钯催化的C–H活化反应的新试剂，该反应能够在温和的催化条件下将甲基和其他烷基从salt盐转移至苯胺衍生物。
• The Use of Polydialkylsiloxanes/Triflic Acid as Derivatization Agents in the Analysis of Sulfur-Containing Aromatics by “Soft”-Ionization Mass Spectrometry
  作者：Zhanna Starkova、Valentina Ilyushenkova、Nikolay Polovkov、Daria Voskressenskaya、Ilya Pikovskoi、Mikhail Tebenikhin、Ella Vtorushina、Anastasiia Kanateva、Roman Borisov、Vladimir Zaikin

  DOI：10.3390/molecules27238600

  日期：——

  action of alkyl iodides and a silver-containing agent is widely used. In the process of developing more economical derivatization methods, we found a rather unexpected possibility of implementing S-alkylation of organic sulfides with commercial polydialkylsiloxanes (alkyl = CH3 or C2H5) in the presence of triflic acid (CF3SO3H) as a superacid co-alkylating agent. For homologous dibenzothiophenes as a typical

  多环芳族含硫化合物广泛分布于油品中，尤其是低挥发分和重质馏分（胶质、沥青质），这就要求开发可靠的油品脱硫、清洁和加工方法时对其进行测定。在这些情况下，基于电喷雾电离 (ESI) 和基质辅助激光解吸/电离 (MALDI) 的“软”电离质谱法特别有效。然而，芳香族含硫化合物具有低极性并且不容易通过这些方法电离。为了克服这个问题，它们通过烷基碘和含银试剂的作用初步转化为硫鎓盐被广泛使用。在开发更经济的衍生化方法的过程中，我们发现在三氟甲磺酸 (CF3SO3H) 作为超强酸共烷基化剂存在的情况下，用商业聚二烷基硅氧烷（烷基 = CH3 或 C2H5）对有机硫化物进行 S-烷基化是一种相当出乎意料的可能性。对于同系二苯并噻吩作为石油含硫芳香族化合物的典型代表，ESI 和 MALDI 质谱显示出相应的 S-烷基硫盐的信号具有高信噪比。提出了所描述的化学转化的合理机制，包括三氟甲磺酸不可或缺的活化作用和
• DNA Interaction and Cleavage Modes of Anthraquinone-Fused Enediynes: A Study on Tiancimycins, Yangpumicins, and Their Semisynthetic Analogues
  作者：Zhongqing Wen、Zhoukang Zhuang、Huiming Liu、Zilong Wang、Xueqiong Feng、Xiangcheng Zhu、Xiaohui Yan、Yanwen Duan、Yong Huang

  DOI：10.1021/acs.jmedchem.3c02049

  日期：2024.3.28

  Dynemicin A has been the sole prototypical anthraquinone-fused enediyne (AFE) explored since its discovery in 1989. This study investigates the distinct DNA binding and cleavage mechanisms of emerging AFEs, represented by tiancimycins and yangpumicins, along with semisynthetic analogues. Our findings reveal their potent cytotoxicity against various tumor cell lines, while 18-methoxy tiancimycin A treatment

  自 1989 年发现以来，动力霉素 A 一直是唯一被探索的原型蒽醌融合烯二炔 (AFE)。这项研究研究了新兴 AFE 的独特 DNA 结合和切割机制，以天赐霉素和杨普米星为代表，以及半合成类似物。我们的研究结果揭示了它们对各种肿瘤细胞系的有效细胞毒性，而 18-甲氧基天西霉素 A 治疗可以显着抑制乳腺肿瘤生长，且毒性最小。最有效的 AFE 之一，即天西霉素 A，优先靶向 DNA 序列 5'-ATT、5'-CTT、5'-GAA、5'-GAT 和 5'-TTA。分子动力学模拟表明，与动力霉素 A 相比，新兴的 AFE 可以更深地嵌入富含 AT 的 DNA 碱基对。重要的是，天西霉素 A 可以在插入模式和嵌入模式之间实现平衡，而无需脱嵌，从而能够选择性切割 T 和 A 碱基。这项研究强调了 AFE 之间微妙的结构变化如何显着影响其 DNA 识别和切割，从而促进未来新型 AFE 的设计，作为抗体药物偶联物的有效和选择性有效负载。
• Kinetic study of trifluoromethylation with s-(trifluoromethyl) dibenzothiophenium salts
  作者：Taizo Ono、Teruo Umemoto

  DOI：10.1016/s0022-1139(96)03392-1

  日期：1996.10

  The kinetic parameters were determined for C-trifluoromethylation of aniline with S-(trifluoromethyl) dibenzothiophenium triflate (1), its 3,7-dinitro derivative (2) and S-(trifluoromethyl) diphenylsulfonium triflate (3) in DMF-d(7). The higher reactivity of heterocyclic 1 compared with non-heterocyclic 3 could be explained on the basis of its greatly enhanced activation entropy (Delta S-not equal: - 11.2 cal mol(-1) K-1 for 1; -47.1 for 3), but not its enhanced activation enthalpy (Delta H-not equal: 21.2 kcal mol(-1) for 1; 12.1 for 3). The aromatic delocalization of the heterocyclic ring may thus be only slightly disturbed by the S-trifluoromethyl substituent. The high reactivity of 2 was attributed to the great electron deficiency caused by two nitro groups in addition to the heterocyclic salt system (Delta H-not equal 17.0 kcal mol(-1), Delta S-not equal -9.1 cal mol(-1) K-1 for 2), The reaction mechanism is discussed; the conventional S(N)2 attack mechanism was ruled out and a mechanism for a side-on attack to the CF3-S bond may possibly be applicable.
• Visible-Light-Promoted Radical C–H Trifluoromethylation of Free Anilines
  作者：Jin Xie、Xiangai Yuan、Ablimit Abdukader、Chengjian Zhu、Jing Ma

  DOI：10.1021/ol500469a

  日期：2014.3.21

  The trifluoromethyl-substituted anilines are biologically active compounds and useful building blocks. In this communication, we have developed the first visible-light-induced radical trifluoromethylation of free anilines with the commercially available and easily handled Togni reagent at room temperature. The resulting products were successfully transformed into a variety of valuable fluorine-containing molecules and heterocyclic compounds. This protocol provides an economical and powerful route to trifluoromethylated free anilines.