5-allyl-1,2,3,4,5-pentamethoxycarbonylcyclopentadiene

• 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: 5-allyl-1,2,3,4,5-pentamethoxycarbonylcyclopentadiene
• 英文别名: pentamethyl 5-prop-2-enylcyclopenta-1,3-diene-1,2,3,4,5-pentacarboxylate
• 化学式: C₁₈H₂₀O₁₀
• 分子量: 396.351
• InChiKey: RYPQPFFYTVUXMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  环戊二烯-1,2,3,4,5-五羧酸戊甲酯 、 3-溴丙烯 生成 5-allyl-1,2,3,4,5-pentamethoxycarbonylcyclopentadiene
  参考文献：
  名称：

  QIU, CHANGLONG;WU, MINYANG;ZHOU, ZHIHONG, CHEM. J. CLIN. UNIV., 8,(1987) N 8, 712-713

  摘要：

  DOI：

文献信息

• 3,3-Sigmatropic Shifts of Allyl Group Along Cyclopentadiene Ring Perimeter
  作者：G. A. Dushenko、I. E. Mikhailov、O. I. Mikhailova、R. M. Minyaev、V. I. Minkin

  DOI：10.1134/s1070363220020012

  日期：2020.2

  Reversible non-degenerate 3,3-sigmatropic shifts of the allyl group along the perimeter of the five-membered ring occurring with energy barriers Delta G degrees(not equal) = 28.5-30.2 kcal/mol (o-dichlorobenzene-d(4)) have been detected in the allyl derivatives of 5-methyl-1,2,3,4-tetramethoxycarbonylcyclopentadiene by NMR method. Using DFT B3LYP/6-311++G(d,p) method, it has been shown that degenerate migrations of the allyl group in the related 5-allyl-1,2,3,4,5-pentamethoxycarbonylcyclopentadiene should occur via 3,3-sigmatropic shift through transition states with conformation of a six-membered ring (chair or boat, with close barriers Delta G degrees(not equal) = 27.4 or 27.7 kcal/mol, respectively). The simulated higher barrier of alternative 1,5-sigmatropic shifts of the allyl group (Delta G degrees(not equal) = 30.8 kcal/mol) indicates the energy preference of the migrations via 3,3-shifts.
• QIU, CHANGLONG;WU, MINYANG;ZHOU, ZHIHONG, CHEM. J. CLIN. UNIV., 8,(1987) N 8, 712-713
  作者：QIU, CHANGLONG、WU, MINYANG、ZHOU, ZHIHONG

  DOI：——

  日期：——