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 | 206660-62-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 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
• CAS: 206660-62-0
• 化学式: C₁₉H₂₄O₁₀
• 分子量: 412.394
• InChiKey: DBDSWGQJDJIIHH-YBCCTHHKSA-N

反应信息

• 作为反应物：
  描述：

  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 在 三溴化磷 作用下， 以 水 、 苯 为溶剂， 反应 48.0h， 以72%的产率得到tetramethyl 1-ethyl-5-methyltetracyclo[3.3.0^1,5.0^2,8.0^4,6]octane-3-exo,7-exo-dibromo-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：

  tetramethyl 1-ethyl-5-methyltetracyclo[3.3.0^1,5.0^2,8.0^4,6]octane-3,7-dione-2,4,6,8-tetracarboxylate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以79%的产率得到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