4,5,10,11,16,17,22,23-Octamethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol | 130147-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,5,10,11,16,17,22,23-Octamethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol
• CAS: 130147-84-1
• 化学式: C₃₆H₄₀O₄
• 分子量: 536.711
• InChiKey: KRSVYYOQVUTJGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5,10,11,16,17,22,23-Octamethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol 在 碘代三甲硅烷 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 28-Butoxy-4,5,10,11,16,17,22,23-octamethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27-triol
  参考文献：
  名称：

  Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies

  摘要：

  Six dissymmetric calix[4]arenes with C4 symmetry consisting of four 3,4-disubstituted phenolic units have been obtained by condensation of the respective 2- or 6-hydroxymethylated phenols. The regular incorporation of the phenolic units into the macrocycle was established on the basis of H-1 NMR spectra and in one case also by X-ray analysis. One example for a calixarene with C2-symmetry consisting of p-cresol and 3,4-dimethylphenol units in alternating sequence was also prepared. Calixarene 4a consisting of 3,4-dimethylphenol units shows a lower energy barrier (DELTAG(double dagger) = 13.4 kcal/mol) for the cone-to-cone inversion in CDCl3 than p-methylcalix[4]arene (DELTAG(double dagger) = 14.6 kcal/mol). The dissymmetric calixarenes 4 could be conformationally fixed by alkylation of the phenolic hydroxyl group. Due to the equivalence of all four phenolic units, mono- and 1,3-di-derivatives could be obtained in addition to tetra derivatives. A tetraester derivative in the cone conformation, like the parent calix[4]arene, crystallizes as a racemate. In solution these tetraester derivatives exist in a distorted cone conformation with C2 symmetry. Dynamic H-1 NMR spectra reveal an energy barrier of DELTAG(double dagger) = 13.3-13.4 kcal/mol for the C2-to-C2 interconversion with the C4-cone as transition state.

  DOI：

  10.1021/jo00067a040
• 作为产物：
  描述：

  4,5-dimethyl-2-hydroxybenzyl alcohol 在 四氯化钛 作用下， 以 1,4-二氧六环 为溶剂， 以17%的产率得到4,5,10,11,16,17,22,23-Octamethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol
  参考文献：
  名称：

  Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies

  摘要：

  Six dissymmetric calix[4]arenes with C4 symmetry consisting of four 3,4-disubstituted phenolic units have been obtained by condensation of the respective 2- or 6-hydroxymethylated phenols. The regular incorporation of the phenolic units into the macrocycle was established on the basis of H-1 NMR spectra and in one case also by X-ray analysis. One example for a calixarene with C2-symmetry consisting of p-cresol and 3,4-dimethylphenol units in alternating sequence was also prepared. Calixarene 4a consisting of 3,4-dimethylphenol units shows a lower energy barrier (DELTAG(double dagger) = 13.4 kcal/mol) for the cone-to-cone inversion in CDCl3 than p-methylcalix[4]arene (DELTAG(double dagger) = 14.6 kcal/mol). The dissymmetric calixarenes 4 could be conformationally fixed by alkylation of the phenolic hydroxyl group. Due to the equivalence of all four phenolic units, mono- and 1,3-di-derivatives could be obtained in addition to tetra derivatives. A tetraester derivative in the cone conformation, like the parent calix[4]arene, crystallizes as a racemate. In solution these tetraester derivatives exist in a distorted cone conformation with C2 symmetry. Dynamic H-1 NMR spectra reveal an energy barrier of DELTAG(double dagger) = 13.3-13.4 kcal/mol for the C2-to-C2 interconversion with the C4-cone as transition state.

  DOI：

  10.1021/jo00067a040

文献信息

• Dissymmetric calix[4]arenes with C2 and C4 symmetry
  作者：Artur Wolff、Volker Boehmer、Walter Vogt、Franco Ugozzoli、Giovanni D. Andreetti

  DOI：10.1021/jo00309a001

  日期：1990.10