2,5,8,11,14-Pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carboxylic acid | 173483-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5,8,11,14-Pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carboxylic acid
• CAS: 173483-35-7
• 化学式: C₁₅H₂₀O₇
• 分子量: 312.32
• InChiKey: GLJBSPHDCWKQQC-UHFFFAOYSA-N

物化性质

• 沸点：
  521.7±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4'-二羟基联苯 、 2,5,8,11,14-Pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carboxylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以80%的产率得到[4-[4-(2,5,8,11,14-Pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carbonyloxy)phenyl]phenyl] 2,5,8,11,14-pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carboxylate
  参考文献：
  名称：

  Syntheses of Monofunctional Derivatives of m-Phenylene-16-crown-5, Bis(m-phenylene)-32-crown-10, and m-Phenylene-p-phenylene-33-crown-10

  摘要：

  A series of monofunctional bis(m-phenylene)-32-crown-10 and m-phenylene-p-phenylene-33-crown-10 derivatives has been synthesized. Cyclization of m- and p-bis(omega-chlorotetraethyleneoxy)benzenes (6) with 5-substituted resorcinols 1 using pseudo-high dilution conditions in DMF and either CsF or K2CO3 as base afforded 5-carbomethoxy-1,3-phenylene-m-phenylene-32-crown-10 (7a, 46%), 5-carbomethoxy-1,3-phenylene-p-phenylene-33-crown-10 (7b, 48%), 5-(benzyloxy)-1,3-phenylen-m-phenylene-32-crown-10 (11b, 51%). Unsubstituted m-phenylene-p-phenylene-33-crown-10 (15) was also made (29%) in this way. Functional group conversions of the bis-phenylene macrocycles yielded 5-carboxy-1,3-phenylene-m-phenylene-32-crown-10 (8a), 5-(hydroxymethyl)-1,3-phenylene-m-phenylene-32-crawn-10 (9a), 5-(bromomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (10a), 5-hydroxy-1,3-phenylene-m-phenylene-32-crown-10 (12a), 5-hydroxy-1,3-phenylene-p-phenylene-33-crown-10 (12b), 5-(phthalimidomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (13a), and 5-(aminomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (14a). Similarly 5-carbomethoxy-1,3-phenylene-16-crown-5 (4) was transformed to the corresponding acid (16), hydroxymethyl (17), formyl(18), bromomethyl (19), phthalimidomethyl (20), azidomethyl (21), and aminomethyl (22) derivatives. These compounds are building blocks for supramolecular assemblies (as shown by the synthesis of a Schiff base (23) from 18 and a diester (24) from 4,4'-biphenol and 17) and useful endcapping or pendant host components of macromolecules.

  DOI：

  10.1021/jo9619948
• 作为产物：
  描述：

  Methyl 2,5,8,11,14-pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以95%的产率得到2,5,8,11,14-Pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carboxylic acid
  参考文献：
  名称：

  Synthesis and Properties of Cholesteryl Esters Bearing 32- and 16-Membered Crown Ethers

  摘要：

  The cholesteryl esters (3b and 3a) of 5-carboxy-1,3-phenylene-16-crown-5 and 5-carboxy-4,6-dichloro-1,3-phenylene-16-crown-5 show cholesteric liquid crystalline behavior but only upon heating samples that were rapidly cooled from the isotropic melt in the case of 3a and a monotropic phase for 3b. The dichloro compound 3a was formed by treatment of the corresponding acid 2 with SOCl2 first and then cholesterol; it is believed that the SOCl2 was contaminated with SO2Cl2, leading to the chlorination of the aromatic ring. The dichloro compound 3a was structurally characterized using single crystal X-ray diffraction. 3a crystallizes in the orthorhombic space group P2(1)2(1)2(1) With unit cell parameters of a = 12.76(4) Angstrom, b = 17.511(5) Angstrom, and c = 18.213 Angstrom. Use of freshly opened SOCl2 produced 3b. The reaction of the acid 2 and cholesterol in the presence of dicyclohexylcarbodiimide yielded the acylisourea 4 as the major product (64%) along with 3b (36%) upon treatment with cholesterol. The dicholesteryl ester 9 of bis(5-carboxy-1,3-phenylene)-32-crown-10 (8a) was also synthesized, and by differential scanning calorimetry (DSC) and polarized optical microscopy no liquid crystalline behavior was observed with this system. Apparently the presence of the semirigid crown in the molecule prevents the two cholesteryl moieties from organizing in independent helices. The complexation ability of this cholesteryl crown (9) with methyl viologen bis(hexafluorophosphate) ([paraquat]. 2[PF6]) (12) in acetone has been examined by H-1 NMR spectroscopy; it showed weaker binding than its simple dimethyl ester analog 8b.

  DOI：

  10.1021/jo950097l