1-mesityl-1,3-dihydro-imidazole-2-selone | 912851-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-mesityl-1,3-dihydro-imidazole-2-selone
• 英文别名: 1-mesitylimidazole-2-selone；Mes(C3H3N2)Se；1-(2,4,6-Trimethylphenyl)imidazole-2-selenol；1-(2,4,6-trimethylphenyl)imidazole-2-selenol
• CAS: 912851-95-7
• 化学式: C₁₂H₁₄N₂Se
• 分子量: 265.217
• InChiKey: GYTIOBJOEGSURT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-mesityl-1,3-dihydro-imidazole-2-selone 在 氧气 作用下， 以 氘代氯仿 为溶剂， 反应 48.0h， 生成 (1-mesityl-imidazol-2-yl)diselenide
  参考文献：
  名称：

  Synthesis and Structural Characterization of 1-Mesityl-1,3-dihydro-imidazole-2-selone and Bis(1-mesitylimidazol-2-yl)diselenide:  Experimental Evidence That the Selone Is More Stable Than the Selenol Tautomer

  摘要：

  1-Mesityl-1,3-dihydro-imidazole-2-selone, (seim(Mes))H, may be obtained from 1-mesitylimidazole via (i) deprotonation with (BuLi)-Li-n, (ii) treatment with elemental selenium, and (iii) addition of HCl(aq). Structural characterization of (seim(Mes))H by X-ray diffraction demonstrates that the compound exists as the selone rather than selenol tautomer, a result that is in accord with DFT calculations. Solutions of (seim(Mes))H are oxidized by air to give bis(1- mesitylimidazol-2-yl) diselenide, (seim(Mes))(2). A corresponding investigation of (seim(Me)) H demonstrates that, in contrast to a previous report, the selenium analogue of methimazole exists in the selone form with a structure analogous to that of methimazole. H-1 and Se-77 NMR studies demonstrate that the (seim(R)) groups of the selone (seim(R))H and diselenide (seim(R))(2) undergo facile exchange on the NMR time scale.

  DOI：

  10.1021/ja063168e
• 作为产物：
  描述：

  (1-mesityl-imidazol-2-yl)diselenide 在 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以64%的产率得到1-mesityl-1,3-dihydro-imidazole-2-selone
  参考文献：
  名称：

  Synthesis and Structural Characterization of 1-Mesityl-1,3-dihydro-imidazole-2-selone and Bis(1-mesitylimidazol-2-yl)diselenide:  Experimental Evidence That the Selone Is More Stable Than the Selenol Tautomer

  摘要：

  1-Mesityl-1,3-dihydro-imidazole-2-selone, (seim(Mes))H, may be obtained from 1-mesitylimidazole via (i) deprotonation with (BuLi)-Li-n, (ii) treatment with elemental selenium, and (iii) addition of HCl(aq). Structural characterization of (seim(Mes))H by X-ray diffraction demonstrates that the compound exists as the selone rather than selenol tautomer, a result that is in accord with DFT calculations. Solutions of (seim(Mes))H are oxidized by air to give bis(1- mesitylimidazol-2-yl) diselenide, (seim(Mes))(2). A corresponding investigation of (seim(Me)) H demonstrates that, in contrast to a previous report, the selenium analogue of methimazole exists in the selone form with a structure analogous to that of methimazole. H-1 and Se-77 NMR studies demonstrate that the (seim(R)) groups of the selone (seim(R))H and diselenide (seim(R))(2) undergo facile exchange on the NMR time scale.

  DOI：

  10.1021/ja063168e

文献信息

• Synthesis and structural characterization of tris(2-seleno-1-mesitylimidazolyl) hydroborato complexes: A new type of strongly electron donating tripodal selenium ligand
  作者：Mao Minoura、Victoria K. Landry、Jonathan G. Melnick、Keliang Pang、Luciano Marchi?、Gerard Parkin

  DOI：10.1039/b608078b

  日期：——

  A new tripodal ligand that features three selenium donors, namely the tris(2-seleno-1-mesitylimidazolyl)hydroborato ligand, [TseMes], has been constructed via the reaction of KBH4 with 1-mesitylimidazole-2-selone; comparison of the IR spectroscopic data of [TseMes]Re(CO)3 with those of a variety of related LRe(CO)3 complexes demonstrates that the [TseMes] ligand is more strongly electron donating than Cp, Cp*, [Tp], [TpMe2] and [TmMes] ligands.

  通过 KBH4 与 1-甲脒咪唑-2-硒酮的反应，我们构建了一种具有三个硒供体的新三元配体，即三(2-硒基-1-甲脒咪唑基)氢硼配体 [TseMes]；将[TseMes]Re(CO)3 的红外光谱数据与各种相关 LRe(CO)3 复合物的红外光谱数据进行比较，结果表明[TseMes]配体比 Cp、Cp*、[Tp]、[TpMe2]和[TmMes]配体具有更强的电子捐赠性。
• Synthesis and Structural Characterization of 1-Mesityl-1,3-dihydro-imidazole-2-selone and Bis(1-mesitylimidazol-2-yl)diselenide:  Experimental Evidence That the Selone Is More Stable Than the Selenol Tautomer
  作者：Victoria K. Landry、Mao Minoura、Keliang Pang、Daniela Buccella、Bryte V. Kelly、Gerard Parkin

  DOI：10.1021/ja063168e

  日期：2006.9.1

  1-Mesityl-1,3-dihydro-imidazole-2-selone, (seim(Mes))H, may be obtained from 1-mesitylimidazole via (i) deprotonation with (BuLi)-Li-n, (ii) treatment with elemental selenium, and (iii) addition of HCl(aq). Structural characterization of (seim(Mes))H by X-ray diffraction demonstrates that the compound exists as the selone rather than selenol tautomer, a result that is in accord with DFT calculations. Solutions of (seim(Mes))H are oxidized by air to give bis(1- mesitylimidazol-2-yl) diselenide, (seim(Mes))(2). A corresponding investigation of (seim(Me)) H demonstrates that, in contrast to a previous report, the selenium analogue of methimazole exists in the selone form with a structure analogous to that of methimazole. H-1 and Se-77 NMR studies demonstrate that the (seim(R)) groups of the selone (seim(R))H and diselenide (seim(R))(2) undergo facile exchange on the NMR time scale.