(+/-)-17-hydroxy-15-oxabicyclo[12.2.2]octadecane-1(17),14(18)-diene-2,16-dione | 240484-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-17-hydroxy-15-oxabicyclo[12.2.2]octadecane-1(17),14(18)-diene-2,16-dione
• 英文别名: 17-Hydroxy-15-oxabicyclo[12.2.2]octadeca-1(17),14(18)-diene-2,16-dione
• CAS: 240484-85-9
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: PXJKRBZQSCMPEB-UHFFFAOYSA-N

物化性质

• 沸点：
  469.062±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.147±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  R(+)-alpha-甲基苄胺 、 (+/-)-17-hydroxy-15-oxabicyclo[12.2.2]octadecane-1(17),14(18)-diene-2,16-dione 以 苯 为溶剂， 反应 1.0h， 生成 (E)-2-((R)-1-Phenyl-ethylamino)-15-oxa-bicyclo[12.2.2]octadeca-1,14(18)-diene-16,17-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：

  1,13-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)tridecane-1,13-dione 以 氯苯 为溶剂， 反应 20.0h， 以87%的产率得到(+/-)-17-hydroxy-15-oxabicyclo[12.2.2]octadecane-1(17),14(18)-diene-2,16-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