Ethyl 2-[[27-(2-ethoxy-2-oxoethoxy)-26,28-dihydroxy-4,5,10,11,16,17,22,23-octamethyl-25-pentacyclo[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-dodecaenyl]oxy]acetate | 130147-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 2-[[27-(2-ethoxy-2-oxoethoxy)-26,28-dihydroxy-4,5,10,11,16,17,22,23-octamethyl-25-pentacyclo[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-dodecaenyl]oxy]acetate
• CAS: 130147-90-9
• 化学式: C₄₄H₅₂O₈
• 分子量: 708.892
• InChiKey: UEWNEWIZNQMFRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  52
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  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 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以86%的产率得到Ethyl 2-[[27-(2-ethoxy-2-oxoethoxy)-26,28-dihydroxy-4,5,10,11,16,17,22,23-octamethyl-25-pentacyclo[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-dodecaenyl]oxy]acetate
  参考文献：
  名称：

  Dissymmetric calix[4]arenes with C2 and C4 symmetry

  摘要：

  DOI：

  10.1021/jo00309a001

文献信息

• Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies
  作者：Giovanni D. Andreetti、Volker Boehmer、J. Graham Jordon、Moniralsadat Tabatabai、Franco Ugozzoli、Walter Vogt、Artur Wolff

  DOI：10.1021/jo00067a040

  日期：1993.7

  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.