1-methyl-2,4-bismethylthio-1,3,5-triazine-6(1H)-one | 72681-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1-methyl-2,4-bismethylthio-1,3,5-triazine-6(1H)-one
• 英文别名: 1-Methyl-4,6-bis(methylsulfanyl)-1,3,5-triazin-2-one
• CAS: 72681-76-6
• 化学式: C₆H₉N₃OS₂
• 分子量: 203.289
• InChiKey: DSLZPBHOAJJEIM-UHFFFAOYSA-N

物化性质

• 沸点：
  292.9±23.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-2,4-bismethylthio-1,3,5-triazine-6(1H)-one 生成 dihydro-3-methyl-4-methylthio-6-methoxy-1,3,5-triazin-2-one
  参考文献：
  名称：

  TOSATO, M. L.;SOCCORSI, L., J. CHEM. SOC. PERKIN TRANS., 1982, N 11, 1321-1326

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methoxy-4,6-bismethylthio-1,3,5-triazine 生成 1-methyl-2,4-bismethylthio-1,3,5-triazine-6(1H)-one
  参考文献：
  名称：

  Tosato, Maria Livia; Soccorsi, Laura, Journal of the Chemical Society. Perkin transactions II, 1982, p. 1321 - 1326

  摘要：

  DOI：

文献信息

• Topochemically controlled solid-state methyl rearrangement in thiocyanurates
  作者：Mark Greenberg、Vitaly Shteiman、Menahem Kaftory

  DOI：10.1107/s0108768101005171

  日期：2001.6.1

  4,6-Dimethoxy-3-methyl-1,3,5-triazine-2(3H)-thione crystallizes in two polymorphic forms, needles and plates. In the needle-shaped crystals (9a) the molecules occupy the crystallographic mirror plane, thus the layers are stacked along the b axis. The molecules of the other polymorph [plate-shape crystals, (9b)] are packed in a herringbone packing mode. Upon heating, (9b) undergoes a phase transition to form (9a). At 378 K the needles undergo O → S topochemically controlled methyl transfer in the solid state to produce 1-methyl-4-methoxy-6-methylthio-1,3,5-triazine-2(1H)-one in 75% yield. The enthalpy of the rearrangement is estimated to be −39.1 kJ mol⁻¹. 1-Methyl-6-methoxy-4-methylthio-1,3,5-triazine-2(1H)-thione crystallizes in space group P2₁ with two crystallographically independent molecules in the asymmetric unit. Compound (9b) undergoes O → S methyl transfer in the solid state at 373 K. The rearrangement is topochemically assisted and the product, 1-methyl-2,4-bismethylthio-1,3,5-triazine-6(1H)-one, is obtained in quantitative yield. The enthalpy of the rearrangement is estimated to be −58.8 kJ mol⁻¹. The crystal structures of the compounds as well as their DSC thermographs are described and discussed. Energy calculation by ab initio methods shows that the driving force for the reactions is the difference between the molecular energies of the pre-rearranged compounds and their products, 54.2 and 59.3 kJ mol⁻¹ in the two cases, respectively.

  4,6-二甲氧基-3-甲基-1,3,5-三嗪-2(3H)-硫酮以针状和板状两种多晶型态结晶。在针状晶体（9a）中，分子占据晶体学镜面，因此晶体层沿 b 轴堆积。而另一种多晶体（板状晶体，(9b)）的分子则以人字形堆积方式堆积。加热时，（9b）发生相变，形成（9a）。在 378 K 的温度下，这些针状物在固态下发生 O → S 表化学控制的甲基转移，生成 1-甲基-4-甲氧基-6-甲硫基-1,3,5-三嗪-2(1H)-酮，产率为 75%。重排焓估计为 -39.1 kJ mol-1。1 甲基-6-甲氧基-4-甲硫基-1,3,5-三嗪-2(1H)-硫酮在空间群 P21 中结晶，不对称单元中有两个晶体学上独立的分子。化合物 (9b) 在 373 K 的固态下发生 O → S 甲基转移。该重排是在拓扑化学的辅助下进行的，产物 1-甲基-2,4-二巯基-1,3,5-三嗪-6(1H)-酮的定量收率很高。重排焓估计为 -58.8 kJ mol-1。报告描述并讨论了这些化合物的晶体结构及其 DSC 热图。利用 ab initio 方法进行的能量计算表明，反应的驱动力是预重排化合物和其产物的分子能量之差，在两种情况下分别为 54.2 和 59.3 kJ mol-1。
• Crystallization and characterization of the prolidase from<i>Pyrococcus furiosus</i>
  作者：Katrina Willingham、Megan J. Maher、Amy M. Grunden、Mousumi Ghosh、Michael W. W. Adams、Hans C. Freeman、J. Mitchell Guss

  DOI：10.1107/s0907444900020187

  日期：2001.3.1

  The prolidase (proline-specific amino dipeptidase) from the hyperthermophilic archaeon Pyrococcus furiosus has been crystallized. The enzyme has been shown to be a homodimer and to require two Co atoms per subunit for optimum activity. Two crystal forms have been obtained under similar growth conditions. Both are monoclinic, space group P2(1). Form I has unit-cell parameters a = 130.4, b = 97.4, c = 129.9 Angstrom, beta = 118.3 degrees. Form II has a smaller unit cell, with a = 56.5, b = 97.3, c = 70.0 Angstrom, beta = 97.1 degrees. If the crystal density is assumed to lie near the center of the normal range then the form I crystals will have four dimers per asymmetric unit, whereas the form II crystals will have only one dimer in each asymmetric unit. Diffraction data have been recorded from native form I and form II crystals to resolutions of 3.2 and 1.95 Angstrom, respectively.
• Tosato, Maria Livia; Soccorsi, Laura, Journal of the Chemical Society. Perkin transactions II, 1982, p. 1321 - 1326
  作者：Tosato, Maria Livia、Soccorsi, Laura

  DOI：——

  日期：——
• TOSATO, M. L.;SOCCORSI, L., J. CHEM. SOC. PERKIN TRANS., 1982, N 11, 1321-1326
  作者：TOSATO, M. L.、SOCCORSI, L.

  DOI：——

  日期：——