2-N-piperidino-5-methyl-1,3-dithiolium-4-thiolate | 85102-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-N-piperidino-5-methyl-1,3-dithiolium-4-thiolate
• 英文别名: 5-methyl-2-piperidino-4-sulfido-1,3-dithiol-2-ium；5-Methyl-2-piperidino-1,3-dithiolium-4-thiolate；5-Methyl-2-piperidin-1-yl-1lambda4,3-dithiacyclopenta-1,5-diene-4-thione；5-methyl-2-piperidin-1-yl-1λ4,3-dithiacyclopenta-1,5-diene-4-thione
• CAS: 85102-68-7
• 化学式: C₉H₁₃NS₃
• 分子量: 231.407
• InChiKey: KOLGLIRKOIDCDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-N-piperidino-5-methyl-1,3-dithiolium-4-thiolate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.0h， 生成 1-(4-hexadecylsulfanyl-5-methyl-1,3-dithiol-2-yl)piperidine
  参考文献：
  名称：

  Abashev; Shklyaeva; Russkikh, Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1652 - 1655

  摘要：

  DOI：
• 作为产物：
  描述：

  triethylammonium piperidinodithiocarbamate 在 二硫化碳 、 乙酸酐 、 三乙胺 作用下， 以 Petroleum ether 、 苯 为溶剂， 生成 2-N-piperidino-5-methyl-1,3-dithiolium-4-thiolate
  参考文献：
  名称：

  MESOIONIC 2-N-CYCLOALKYLAMINO-5-ALKYL-1,3-DITHIOLIUM-4-THIOLATES

  摘要：

  Seven 2-(N-cycloalkylamino-1,3-dithiocarbamoyl)-carboxylic acids and seven mesoionic 2-N-cycloalkylamino-5-alkyl-1,3-dithiolium-4-thiolates have been conveniently synthesized. They were characterized by elemental analysis, I.R., U.V., mass and H-1 NMR spectrometry, plus C-13 NMR spectrometry in some cases. Important questions concerning the structure of the mesoionic compounds, relevant to mesoionic compounds in general, are addressed. In particular, we refer to the degree of separation of regions of positive and negative charge, bond orders, electron and charge delocalization and aromaticity. In this discussion we cite some of our X-ray diffraction and theoretical studies. We conclude that there are regions of positive and negative charge in which there is delocalization of electrons and charge with bond orders between 1 and 2. However, the shared regions are separated by what are essentially single bonds. Thus, they, and mesoionic compounds in general, should not be considered as formally aromatic. This is supported by estimates of Bird Aromaticity indices-experimentally based for two of the title mesoionic compounds-of the order of 50: substantially less than values for thiophene and pyrrole and much less than values for benzene and pyridine. Finally, based on this discussion, we introduce a new notation for the structures of mesoionic compounds which we believe more accurately represents both the bonding situation and the chemical patterns of reactivity of such compounds.

  DOI：

  10.1080/10426509608029640

文献信息

• New redox active ligands involving a tetrathiafulvalene vinylogue backbone
  作者：Michel Guerro、Ngoc Ha Pham、Julien Massue、Nathalie Bellec、Dominique Lorcy

  DOI：10.1016/j.tet.2008.03.032

  日期：2008.5

  Two synthetic approaches towards a new bisthiopicoline substituted vinylogous tetrathiafulvalene (TTFV) are described. As evidenced by electrochemistry and 1H NMR studies, this redox active ligand shows excellent coordinating properties towards Zn2+ metal ion.

  描述了一种针对新的双硫代吡啶啉取代的乙烯基四硫富富瓦烯（TTFV）的两种合成方法。如通过电化学和1 H NMR研究所证明的，该氧化还原活性配体对Zn 2+金属离子显示出优异的配位性能。
• Preparation of dithiadiazafulvalene precursors: 2-piperidino-2,3-dihydro-1,3-thiazoles or 2-unsubstituted 2,3-dihydro-1,3-thiazoles from the reduction of the corresponding 2-piperidino mesoionic thiazoles
  作者：Mohammed Bssaibis、Albert Robert、Abdel Aziz Souizi

  DOI：10.1039/p19940001469

  日期：——

  3-aryl-4-alkylthio-5-aryl- or -alkyl-2,3-dihydro-1,3-thiazoles 10 have been prepared starting from mesoionic 5-alkyl- or 5-aryl-2-piperidino-1,3-thiazole-4-thiolates 6. After alkylation of the mesoionic compound, the best conditions to isolate these two dihydrothiazoles were established from a mechanistic study of the reduction. Compound 8 is known to give dithiadiazafulvalenes through its thiazolium tetrafluoroborate

  取决于实验条件，是2-哌啶子基-3-芳基-4-烷基硫代5-芳基-或-烷基-2,3-二氢-1,3-噻唑8或2-未取代的3-芳基-4从中离子的5-烷基-或5-芳基-2-哌啶子基-1,3-噻唑-4-开始制备了-烷硫基-5-芳基-或-烷基-2,3-二氢-1,3-噻唑10。硫醇盐6。对中离子化合物进行烷基化后，从还原反应的机理研究中确定了分离这两种二氢噻唑的最佳条件。已知化合物8通过其噻唑鎓四氟硼酸盐得到二噻二氮富瓦烯。我们在这里表明，这些盐也可以从10获得。
• ——
  作者：G. G. Abashev、E. V. Shklyaeva、A. G. Tenishev、D. N. Korekov

  DOI：10.1023/a:1025647112804

  日期：——
• Mesoions as versatile intermediates in tetrathiafulvalene synthesis
  作者：M. Joergensen、K. A. Lerstrup、K. Bechgaard

  DOI：10.1021/jo00019a041

  日期：1991.9
• Bis(1,3-dithiole-2-chalcogenones) and tetrathiafulvalenes in the synthesis of bridged tetrathiafulvalene-containing structures
  作者：G. G. Abashev、A. Yu. Bushueva、K. Yu. Lebedev、E. V. Shklyaeva

  DOI：10.1134/s1070428007010186

  日期：2007.1

  Bis(1,3-dithiole-2-chalcogenones) in which the 1,3-dithiole fragments are linked through various bridging groups were synthesized by different methods. Some of these compounds were converted into substituted tetrathiafulvalenes with bridged 1,3-dithiole rings. The same structures were synthesized from preliminarily prepared symmetric tetrathiafulvalenes containing 2-cyanoethylsulfanyl groups in both 1,3-dithiole rings. Similar spacers were used to bridge two tetrathiafulvalene fragments. Syntheses of the involved initial compounds were described.