m-Benzoldipentansaeure | 54698-77-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: m-Benzoldipentansaeure
• 英文别名: 5-[3-(4-Carboxybutyl)phenyl]pentanoic acid；5-[3-(4-carboxybutyl)phenyl]pentanoic acid
• CAS: 54698-77-0
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: KZRSCPOWICBCQX-UHFFFAOYSA-N

物化性质

• 沸点：
  508.3±43.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  m-Benzoldipentansaeure 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-[3-[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
• 作为产物：
  描述：

  二甲基3,3'-(1,3-亚苯基)二丙酸酯 在 lithium aluminium tetrahydride 、 硫酸 、 sodium bromide 作用下， 以 乙醚 为溶剂， 生成 m-Benzoldipentansaeure
  参考文献：
  名称：

  Synthesis of oxometacyclophanes with the Dieckmann condensation

  摘要：

  DOI：

  10.1021/jo00898a025

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.
• Synthesis of oxometacyclophanes with the Dieckmann condensation
  作者：Clarence W. Schimelpfenig

  DOI：10.1021/jo00898a025

  日期：1975.5