5-[5-[4-[5-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-5-hydroxypentyl]phenyl]-1-hydroxypentylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione | 247599-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[5-[4-[5-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-5-hydroxypentyl]phenyl]-1-hydroxypentylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 247599-49-1
• 化学式: C₂₈H₃₄O₁₀
• 分子量: 530.572
• InChiKey: CYKCWKOHUJODGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  丙酮 、 5-[5-[4-[5-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-5-hydroxypentyl]phenyl]-1-hydroxypentylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 以 甲苯 为溶剂， 反应 1.0h， 以59%的产率得到6-[4-[4-[4-(2,2-Dimethyl-6-oxo-1,3-dioxin-4-yl)butyl]phenyl]butyl]-2,2-dimethyl-1,3-dioxin-4-one
  参考文献：
  名称：

  Convenient Synthesis of Chiral Cyclophanes that Can Coordinate to Metals

  摘要：

  Optically pure cyclophanes possessing a 1,3-dicarbonyl moiety were conveniently synthesized from alkanedioyl dichloride in four steps. The intramolecular [4+2]cycloaddition of bis(acylketene)s generated by thermal decomposition of bis(4,6-dioxo-1,3-dioxane) proceeded smoothly, giving cyclophane pyranones in high yields. The compounds possessing 7-10 bridging methylenes were resolved by imine formation with (R)-1-phenylethylamine, followed by basic hydrolysis. These cyclophanes are optically active versions of acetylacetone or salicylaldehyde and formed complexes with metals such as copper and europium. X-ray analysis of the chiral copper complex indicated the pentacoordinated structure of the copper metal with syn configuration of the two bridging chains.

  DOI：

  10.1021/ja983907u
• 作为产物：
  描述：

  4,4'-p-phenylenebis(valeric acid) 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 5-[5-[4-[5-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-5-hydroxypentyl]phenyl]-1-hydroxypentylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Convenient Synthesis of Chiral Cyclophanes that Can Coordinate to Metals

  摘要：

  Optically pure cyclophanes possessing a 1,3-dicarbonyl moiety were conveniently synthesized from alkanedioyl dichloride in four steps. The intramolecular [4+2]cycloaddition of bis(acylketene)s generated by thermal decomposition of bis(4,6-dioxo-1,3-dioxane) proceeded smoothly, giving cyclophane pyranones in high yields. The compounds possessing 7-10 bridging methylenes were resolved by imine formation with (R)-1-phenylethylamine, followed by basic hydrolysis. These cyclophanes are optically active versions of acetylacetone or salicylaldehyde and formed complexes with metals such as copper and europium. X-ray analysis of the chiral copper complex indicated the pentacoordinated structure of the copper metal with syn configuration of the two bridging chains.

  DOI：

  10.1021/ja983907u