Methyl(3-methyl-3H-thiazol-2-ylidene)sulfonium iodide | 33167-42-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Methyl(3-methyl-3H-thiazol-2-ylidene)sulfonium iodide
• 英文别名: 3-methyl-2-(methylthio)thiazolium iodide；2-Methylmercapto-3-methyl-thiazoliumiodid；3-methyl-2-methylsulfanyl-thiazolium; iodide；3-Methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide；3-methyl-2-methylsulfanyl-1,3-thiazol-3-ium;iodide
• CAS: 33167-42-9
• 化学式: C₅H₈NS₂*I
• 分子量: 273.162
• InChiKey: KLNFYAHMUXXSGF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  Methyl(3-methyl-3H-thiazol-2-ylidene)sulfonium iodide 生成 bis-(3-methyl-3H-thiazol-2-ylidene)-hydrazine
  参考文献：
  名称：

  Huenig,S.; Sauer,G., Justus Liebigs Annalen der Chemie, 1971, vol. 748, p. 173 - 188

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲硫基噻唑 、 碘甲烷 以 甲醇 为溶剂， 反应 8.0h， 生成 Methyl(3-methyl-3H-thiazol-2-ylidene)sulfonium iodide
  参考文献：
  名称：

  噻唑橙类似物的合成和抗衰老评价。

  摘要：

  以前，花菁化合物已显示出优异的体外和体内有希望的抗衰老功效，但这些试剂的潜在毒性令人担忧。噻唑橙（商业花菁）（噻唑橙）（（Z）-1-甲基-4-（（3-甲基苯并[ d ]噻唑-2（3 H）-亚烷基）甲基）喹啉-1-盐的一系列22类似物为了提高此类化合物的选择性，同时又保持功效，合成了具有抗衰老活性的染料。在喹啉鎓环系统上具有取代基的花青显示出对利什曼原虫多酚新戊二酸弹药的有效力，与母体化合物相差不大（IC 5012-42 nM），而环脱位类似物的效力和毒性均较低。当将合成的寡核苷酸与选定的类似物（ΔTm≤5°C）一起孵育时，DN​​A熔解温度的变化适中，而环脱位类似物对该参数的影响最小。尽管目标化合物具有很高的无毒杀虫效力，但它们的毒性和相对平缓的SAR提示需要有关这些分子的靶标的进一步信息，以帮助其发展为无毒杀伤菌。

  DOI：

  10.1016/j.bmcl.2019.126725

文献信息

• The impact of sulfur functionalisation on nitrogen-based ionic liquid cations
  作者：Ana R. Santos、Magnus W. D. Hanson-Heine、Nicholas A. Besley、Peter Licence

  DOI：10.1039/c8cc05515g

  日期：——

  the impact of sulfur containing substituents on the electronic structure of a series of N-based cations, all with a common anion, [NTf2]−. The experiments reveal complexity and perturbation of delocalised systems which cannot be easily interpreted by NMR and XPS alone, DFT provides critical insight into bonding and underpins the assignment of spectra and development of deconstruction models for each

  已经证明，可以通过操纵结构和引入官能团来优雅地调节离子液体（IL）中的键合和相互作用。在这里，我们使用XPS来研究含硫取代基对一系列N基阳离子的电子结构的影响，这些阳离子均带有一个共同的阴离子[NTf 2 ] -。实验揭示了离域系统的复杂性和微扰性，仅凭NMR和XPS难以轻易解释，DFT为键合提供了关键见解，并为每个研究的系统提供了光谱分配和解构模型开发的基础。
• 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.
• Chanon,M. et al., Bulletin de la Societe Chimique de France, 1968, p. 2881 - 2885
  作者：Chanon,M. et al.

  DOI：——

  日期：——