1,8-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)octane-1,8-dione

• 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: 1,8-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)octane-1,8-dione
• 英文别名: 5-[8-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1,8-dihydroxyoctylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[8-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1,8-dihydroxyoctylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• 化学式: C₂₀H₂₆O₁₀
• 分子量: 426.42
• InChiKey: DKXXYEWBKBEBEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  1,8-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)octane-1,8-dione 以 氯仿 为溶剂， 反应 20.0h， 以9%的产率得到23,25-Dihydroxy-10,21-dioxa-tricyclo[18.2.2.2^9,12]hexacosa-1(23),9(26),12(25),20(24)-tetraene-2,11,13,22-tetraone
  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：

  丙二酸环(亚)异丙酯 、 1,8-二辛酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以76%的产率得到1,8-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)octane-1,8-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

文献信息

• TWI588139
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.