bis(5-carboxy-1,3-phenylene)-20-crown-6 | 198328-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(5-carboxy-1,3-phenylene)-20-crown-6
• 英文别名: 2,5,8,14,17,20-Hexaoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarboxylic acid；2,5,8,14,17,20-hexaoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarboxylic acid
• CAS: 198328-20-0
• 化学式: C₂₂H₂₄O₁₀
• 分子量: 448.427
• InChiKey: PEKYFINLTSHRPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Dimethyl 2,5,8,14,17,20-hexaoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarboxylate 在 四丁基氢氧化铵 作用下， 以 水 为溶剂， 反应 24.0h， 以70%的产率得到bis(5-carboxy-1,3-phenylene)-20-crown-6
  参考文献：
  名称：

  Polyrotaxanes by in situ self threading during polymerization of functional macrocycles. Part 2: Poly(ester crown ether)s

  摘要：

  Poly(ester crown ether)s were synthesized by direct condensation of bis(5-carboxy-m-phenylene)-(3x + 2)-crown-x, x = 6, 8 and 10 (1a, 1b and 1c) with bisphenols via the Higashi method. The formation of higher molecular weight poly(ester crown ether) 5 from the 32-membered crown ether 1c and bisphenol-A (2a) as compared to polyester 3 from 20-membered crown ether 1a and bisphenol-A, polyester 4 made from the 26-membered crown ether 1b and bisphenol-A (2a) and polyester 6 derived from 32-membered 1c and bis(p-t-butylphenyl)-bis(p-hydroxyphenyl)methane (2b) under identical conditions is believed to be the result of threading (rotaxane formation) in 5 but no or less threading in 3, 4 or 6; indeed polyester 3 provides a control because its macrocyclic component (1a) too small to be threaded, even by a polymethylene chain. Threading in 5 was undetectable through NOESY experiments. However, melt polymerization of bis(5-hydroxymethyl-m-phenylene)-32-crown-10 (7) with sebacoyl chloride (8) gave an insoluble, but swellable elastomeric material 9, a polyrotaxane network, as a result of more extensive in situ threading brought about by hydrogen bonding of the crown ether with the alcohol moieties in the more concentrated medium. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00957-5

文献信息

• Polyrotaxanes by in situ self threading during polymerization of functional macrocycles. Part 2: Poly(ester crown ether)s
  作者：Harry W Gibson、Devdatt S Nagvekar、Jason Powell、Caiguo Gong、William S Bryant

  DOI：10.1016/s0040-4020(97)00957-5

  日期：1997.11

  Poly(ester crown ether)s were synthesized by direct condensation of bis(5-carboxy-m-phenylene)-(3x + 2)-crown-x, x = 6, 8 and 10 (1a, 1b and 1c) with bisphenols via the Higashi method. The formation of higher molecular weight poly(ester crown ether) 5 from the 32-membered crown ether 1c and bisphenol-A (2a) as compared to polyester 3 from 20-membered crown ether 1a and bisphenol-A, polyester 4 made from the 26-membered crown ether 1b and bisphenol-A (2a) and polyester 6 derived from 32-membered 1c and bis(p-t-butylphenyl)-bis(p-hydroxyphenyl)methane (2b) under identical conditions is believed to be the result of threading (rotaxane formation) in 5 but no or less threading in 3, 4 or 6; indeed polyester 3 provides a control because its macrocyclic component (1a) too small to be threaded, even by a polymethylene chain. Threading in 5 was undetectable through NOESY experiments. However, melt polymerization of bis(5-hydroxymethyl-m-phenylene)-32-crown-10 (7) with sebacoyl chloride (8) gave an insoluble, but swellable elastomeric material 9, a polyrotaxane network, as a result of more extensive in situ threading brought about by hydrogen bonding of the crown ether with the alcohol moieties in the more concentrated medium. (C) 1997 Elsevier Science Ltd.