(1-mesityl-imidazol-2-yl)diselenide | 912851-96-8

• 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-imidazol-2-yl)diselenide
• 英文别名: 1-(2,4,6-Trimethylphenyl)-2-[[1-(2,4,6-trimethylphenyl)imidazol-2-yl]diselanyl]imidazole；1-(2,4,6-trimethylphenyl)-2-[[1-(2,4,6-trimethylphenyl)imidazol-2-yl]diselanyl]imidazole
• CAS: 912851-96-8
• 化学式: C₂₄H₂₆N₄Se₂
• 分子量: 528.417
• InChiKey: KALDKGIUGUUHNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-mesityl-imidazol-2-yl)diselenide 在 sodium 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 1.0h， 生成
  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-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

文献信息

• Applications of Bis(1-R-imidazol-2-yl)disulfides and Diselenides as Ligands for Main-Group and Transition Metals:  κ²-(N<i>,</i>N) Coordination, S−S Bond Cleavage, and S−S/E−E (E = S, Se) Bond Metathesis Reactions
  作者：Joshua S. Figueroa、Kevin Yurkerwich、Jonathan Melnick、Daniela Buccella、Gerard Parkin

  DOI：10.1021/ic701228y

  日期：2007.10.1

  Ni(PMe3)4 effects cleavage of the disulfide bond of (mim(Bu)(t))2 to give square-planar trans-Ni(PMe3)2(mim(Bu)(t))2 in which the (mim(Bu)(t)) ligands coordinate via nitrogen rather than sulfur, a most uncommon coordination mode for this class of ligands. Although [kappa2-(mim(R))2]MCl2 (M = Fe, Co, Ni, Zn) are not subject to homolytic cleavage of the S-S bond because the tetravalent state is not readily

  双(1-R-咪唑-2-基)二硫化物(mim(R))2 (R = Ph, Bu(t))和二硒化物(seim(Mes))2作为二齿N,N-主族金属和过渡金属的供体配体。例如，[kappa2-(mim(Bu)(t))2]MCl2 (M = Fe, Co, Ni, Zn), [kappa2-(mim(Ph))2]MCl2 (M = Co, Zn), [kappa2-(mim(Bu)(t))2]CuX (X = Cl, I) 和 [kappa2-(seim(Mes))2]MCl2 (M = Fe, Co, Ni) (mim(Bu)(t))2 或 (seim(Mes))2 与相应的金属卤化物，并已通过 X 射线衍射进行结构表征。另一方面，零价镍配合物 Ni(PMe3)4 影响 (mim(Bu)(t))2 的二硫键断裂，得到方形平面反式 Ni(PMe3)2(mim(Bu)(t) ))2 其中 (mim(Bu)(t))
• 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.