1,2-bis[4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)butyl]benzene | 240484-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-bis[4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)butyl]benzene
• 英文别名: 6-[4-[2-[4-(2,2-Dimethyl-6-oxo-1,3-dioxin-4-yl)butyl]phenyl]butyl]-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 240484-80-4
• 化学式: C₂₆H₃₄O₆
• 分子量: 442.552
• InChiKey: FIWYFJYHFPAJDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis[4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)butyl]benzene 在 氢氧化钾 作用下， 以 四氢呋喃 、 氯苯 、 苯 为溶剂， 反应 41.0h， 生成 (+/-)-7,8-benzo-16-hydroxy-14-oxabicyclo[11.2.2]heptadecane-1(16),7,13(17)-triene-2,15-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
• 作为产物：
  描述：

  1,2-benzenedipentanoic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 1,2-bis[4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)butyl]benzene
  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

文献信息

• Convenient Synthesis of Chiral Cyclophanes that Can Coordinate to Metals
  作者：Masayuki Sato、Fumiaki Uehara、Kayo Sato、Masahiko Yamaguchi、Chizuko Kabuto

  DOI：10.1021/ja983907u

  日期：1999.9.1

  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.