5-phenyl-3-methylthio-1,2-dithiolium iodide | 4849-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-phenyl-3-methylthio-1,2-dithiolium iodide
• 英文别名: 3-Methylmercapto-5-phenyl-1,2-dithiolium-jodid；3-Methylmercapto-5-phenyl-1,2-dithiolium；3-Methylmercapto-5-phenyl-dithiol-1,2-ylium；3-methylsulfanyl-5-phenyl-[1,2]dithiolylium; iodide；3-Methylmercapto-5-phenyl-[1,2]dithiolylium; Jodid；3-Methylsulfanyl-5-phenyldithiol-2-ium;iodide；3-methylsulfanyl-5-phenyldithiol-2-ium;iodide
• CAS: 4849-59-6
• 化学式: C₁₀H₉S₃*I
• 分子量: 352.284
• InChiKey: NHXJMMHSAUJTOD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-phenyl-3-methylthio-1,2-dithiolium iodide 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 碘 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 52.83h， 生成 N-methyl-5-phenylthiophen-3-amine
  参考文献：
  名称：

  C-2上具有各种取代基的3-烷基氨基-5-芳基噻吩的便捷合成及反应机理的研究

  摘要：

  在乙酸汞（II）的存在下，用活性亚甲基化合物（包括β-酮酸酯，硝基甲烷，氰基乙酸，对甲苯磺酰基丙酮，4-硝基苯乙酸和4-乙基苯基乙酸）处理亚硫酰芳基烯酮S，N-缩醛。 CH（2）Cl（2）在室温下。这些反应以良好的收率得到了含有各种取代基的3-烷基氨基-5-芳基噻吩，这些取代基分别在C-2上包含烷氧羰基，硝基，氰基，对甲苯磺酰基，4-硝基苯基和二乙基膦酰基。在相同条件下，使3-甲基氨基-3-甲基硫基-1-苯基硫代丙烯与丙二酸或Meldrum酸反应，得到3-甲基氨基-5-苯基噻吩。同样地，使用各种可烯丙基环酮（例如4-羟基-6-甲基-2-吡喃酮）处理3-甲基氨基-3-甲基硫基-1-苯基硫代丙烯，

  DOI：

  10.1021/jo991884b
• 作为产物：
  描述：

  5-苯基二硫杂环戊烯-3-硫酮 、 碘甲烷 以 丙酮 为溶剂， 反应 48.0h， 生成 5-phenyl-3-methylthio-1,2-dithiolium iodide
  参考文献：
  名称：

  C-2上具有各种取代基的3-烷基氨基-5-芳基噻吩的便捷合成及反应机理的研究

  摘要：

  在乙酸汞（II）的存在下，用活性亚甲基化合物（包括β-酮酸酯，硝基甲烷，氰基乙酸，对甲苯磺酰基丙酮，4-硝基苯乙酸和4-乙基苯基乙酸）处理亚硫酰芳基烯酮S，N-缩醛。 CH（2）Cl（2）在室温下。这些反应以良好的收率得到了含有各种取代基的3-烷基氨基-5-芳基噻吩，这些取代基分别在C-2上包含烷氧羰基，硝基，氰基，对甲苯磺酰基，4-硝基苯基和二乙基膦酰基。在相同条件下，使3-甲基氨基-3-甲基硫基-1-苯基硫代丙烯与丙二酸或Meldrum酸反应，得到3-甲基氨基-5-苯基噻吩。同样地，使用各种可烯丙基环酮（例如4-羟基-6-甲基-2-吡喃酮）处理3-甲基氨基-3-甲基硫基-1-苯基硫代丙烯，

  DOI：

  10.1021/jo991884b

文献信息

• Charbonnel-Jobic, Gaelle; Guemas, Jean-Pierre; Adelaere, Bruno, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 624 - 636
  作者：Charbonnel-Jobic, Gaelle、Guemas, Jean-Pierre、Adelaere, Bruno、Parrain, Jean-Luc、Quintard, Jean-Paul

  DOI：——

  日期：——
• Woronkow; Broun; Karpenko, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1927,1939
  作者：Woronkow、Broun、Karpenko

  DOI：——

  日期：——
• Specific Molecular Orbital Contributions to Nucleophilicity. The Thiocarbonyl Group as Priviledged Monitor to Pinpoint Active and Less Active Molecular Orbitals in Reactions with Methylating Agents
  作者：M. Arbelot、A. Allouche、K. F. Purcell、M. Chanon

  DOI：10.1021/jo00113a010

  日期：1995.4

  The rate constants for 41 compounds bearing a C=S function reacting with MeX (X = I, Tos) span 7 orders of magnitude. The PES spectra of these compounds display two very low energy peaks, which stand clearly apart from the other peaks. These two peaks correspond to the pi orbitals of the C-S group; one is its CS pi bonding orbital oriented out of the molecular plane (pi(CS)) and the other its p-type in-plane lone pair orbital (pi(S)). For some of the compounds, the HOMO is the pi(CS) orbital and for others the HOMO is the ns lone pair orbital. The best correlation (R = 0.96) between rate constants h and PES data is obtained when In(k) is plotted against the inverse of PES energy of the pi(S) lone pair orbital. Whether this lone pair orbital is the HOMO or the next lower HOMO has no importance. A modest correlation (R = 0.78) is obtained when In(k) is plotted against the inverse of PES energy of the pi(CS) bonding orbital, An attempt to correlate the calculated energy of the third highest occupied orbital (from AM1 calculations) with In(h) provides a complete scattering of data (R < 0.1), but the calculated energy of the second lone pair orbital sigma(S) (approximate to 90 kcal mol-l deeper than the HOMO) correlates reasonably with In(h) (R = 0.88). The energies of the S 2s and 2p core orbitals (calculated for 13 cyclic compounds with the HF/3-21G technique to be 4000 to 5500 kcal mol(-1) deeper than HOMO) correlate with In(k) (R = 0.86) as well as does that of the second lone pair orbital os. These results are the first where both frontier orbitals and core orbitals display correlation with overall reactivity. They are discussed in terms of direct (perturbational) versus indirect (nonperturbational) concepts.
• Mysyk, Dmitrii D.; Perepichka, Igor F., Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 527 - 530
  作者：Mysyk, Dmitrii D.、Perepichka, Igor F.

  DOI：——

  日期：——
• McKinnon, David M.; Duncan, K.Ann; McKinnon, Aileen M., Canadian Journal of Chemistry, 1985, vol. 63, p. 882 - 886
  作者：McKinnon, David M.、Duncan, K.Ann、McKinnon, Aileen M.、Spevack, Perry A.

  DOI：——

  日期：——