tetramethyl (1S,3aR,4R,6aR)-3a-ethyl-2,5-dihydroxy-6a-methyl-1,4-dihydropentalene-1,3,4,6-tetracarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tetramethyl (1S,3aR,4R,6aR)-3a-ethyl-2,5-dihydroxy-6a-methyl-1,4-dihydropentalene-1,3,4,6-tetracarboxylate
• 化学式: C₁₉H₂₄O₁₀
• 分子量: 412.394
• InChiKey: VZPZSBQFBAYUAF-FXCLICFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tetramethyl (1S,3aR,4R,6aR)-3a-ethyl-2,5-dihydroxy-6a-methyl-1,4-dihydropentalene-1,3,4,6-tetracarboxylate 在 sodium tetrahydroborate 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.0h， 生成 tetramethyl 1-ethyl-5-methyltetracyclo[3.3.0^1,5.0^2,8.0^4,6]octane-3-endo,7-endo-diol-2,4,6,8-tetracarboxylate
  参考文献：
  名称：

  The Search for Homoaromatic Semibullvalenes. 5.¹ 1,5-Dimethyl-2,4,6,8-semibullvalenetetracarboxylic Dianhydride

  摘要：

  The synthesis and study of a novel bisannelated semibullvalene that is calculated to be a neutral homoaromatic ground state molecule is presented. Through variable-temperature X-ray, C-13 solution-phase NMR, and C-13 solid-state CP-MAS NMR studies and by a modified Saunders' isotopic perturbation method, 1,5-dimethyl-2,4,6,8-semibullvalenetetracarboxylic dianhydride is shown to be a highly fluxional molecule that is not homoaromatic in the solution or solid states, The barrier to the Cope rearrangement of this dianhydride, in solution, is estimated (from 125 MHz C-13 NMR data) to be less than 14 kJ mol(-1).

  DOI：

  10.1021/jo972010x
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 2,3-戊二酮 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 tetramethyl (1R,3aR,4R,6aR)-3a-ethyl-2,5-dihydroxy-6a-methyl-1,4-dihydropentalene-1,3,4,6-tetracarboxylate 、 tetramethyl (1S,3aR,4R,6aR)-3a-ethyl-2,5-dihydroxy-6a-methyl-1,4-dihydropentalene-1,3,4,6-tetracarboxylate
  参考文献：
  名称：

  Williams, Richard Vaughan; Gadgil, Vijay R.; Vij, Ashwani, Journal of the Chemical Society. Perkin transactions I, 1997, # 9, p. 1425 - 1428

  摘要：

  DOI：

文献信息

• Williams, Richard Vaughan; Gadgil, Vijay R.; Vij, Ashwani, Journal of the Chemical Society. Perkin transactions I, 1997, # 9, p. 1425 - 1428
  作者：Williams, Richard Vaughan、Gadgil, Vijay R.、Vij, Ashwani、Cook, James M.、Kubiak, Greg、Huang, Qi

  DOI：——

  日期：——
• The Search for Homoaromatic Semibullvalenes. 5.¹ 1,5-Dimethyl-2,4,6,8-semibullvalenetetracarboxylic Dianhydride
  作者：Richard Vaughan Williams、Vijay R. Gadgil、Kamlesh Chauhan、Lloyd M. Jackman、Errol Fernandes

  DOI：10.1021/jo972010x

  日期：1998.5.1

  The synthesis and study of a novel bisannelated semibullvalene that is calculated to be a neutral homoaromatic ground state molecule is presented. Through variable-temperature X-ray, C-13 solution-phase NMR, and C-13 solid-state CP-MAS NMR studies and by a modified Saunders' isotopic perturbation method, 1,5-dimethyl-2,4,6,8-semibullvalenetetracarboxylic dianhydride is shown to be a highly fluxional molecule that is not homoaromatic in the solution or solid states, The barrier to the Cope rearrangement of this dianhydride, in solution, is estimated (from 125 MHz C-13 NMR data) to be less than 14 kJ mol(-1).