1-(4-chlorophenyl)-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octa-3,7-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1-(4-chlorophenyl)-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octa-3,7-dione
• 英文别名: (3aR,6aR)-6a-(4-chlorophenyl)-3,3,6,6-tetramethyl-3aH-furo[3,2-b]furan-2,5-dione
• 化学式: C₁₆H₁₇ClO₄
• 分子量: 308.762
• InChiKey: KYZTWBUJMXVZFT-BZNIZROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴代异丁酸甲酯 、 (4-氯苯基)-氧代乙醛 在 锌 作用下， 以 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 0.5h， 以68%的产率得到1-(4-chlorophenyl)-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octa-3,7-dione
  参考文献：
  名称：

  摘要：

  Methyl 2-bromo-2-methylpropionate reacts with zinc and arylglyoxals under conditions of Reformatsky reaction in ether-HMPA mixture to afford 1-aryl-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octane-3,7-diones in 68-85% yield. Methyl 2-bromopropionate reacts with zinc and 4-bromophenylglyoxal in the same way giving the bicyclic product in 28% yield. The bromination of 1-(4-tolyl)-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octane-3,7-dione with bromosuccinimide results in successive replacement of hydrogens in the tolyl moiety by bromine. The calculation of formation enthalpy for stereoisomers of compounds obtained in AM1 approximation predicts the highest stability for chair-type conformation with eclipsed position of substituents at C-1 and C-5 atoms.

  DOI：

  10.1023/a:1015530120212

文献信息

• ——
  作者：V. V. Shchepin、D. V. Fotin、A. N. Nedugov、V. V. Fotin、M. I. Vakhrin

  DOI：10.1023/a:1011629226986

  日期：——
• ——
  作者：V. V. Shchepin、D. V. Fotin、A. N. Nedugov、V. V. Fotin

  DOI：10.1023/a:1015530120212

  日期：——

  Methyl 2-bromo-2-methylpropionate reacts with zinc and arylglyoxals under conditions of Reformatsky reaction in ether-HMPA mixture to afford 1-aryl-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octane-3,7-diones in 68-85% yield. Methyl 2-bromopropionate reacts with zinc and 4-bromophenylglyoxal in the same way giving the bicyclic product in 28% yield. The bromination of 1-(4-tolyl)-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octane-3,7-dione with bromosuccinimide results in successive replacement of hydrogens in the tolyl moiety by bromine. The calculation of formation enthalpy for stereoisomers of compounds obtained in AM1 approximation predicts the highest stability for chair-type conformation with eclipsed position of substituents at C-1 and C-5 atoms.