11,23-dibromo-25,26,27,28-tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-5,17-dicarbaldehyde | 172472-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 11,23-dibromo-25,26,27,28-tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-5,17-dicarbaldehyde
• CAS: 172472-59-2
• 化学式: C₄₂H₄₆Br₂O₆
• 分子量: 806.632
• InChiKey: RBYZHBOJYAKOBW-UHFFFAOYSA-N

物化性质

• 沸点：
  884.2±65.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.67
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  11,23-dibromo-25,26,27,28-tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-5,17-dicarbaldehyde 在 三(三甲代甲硅烷基)亚磷酸盐 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以97%的产率得到25,26,27,28-tetrapropoxycalix[4]arene-11,23-dibromo-5,17-bis(α-hydroxymethylphosphonic acid)
  参考文献：
  名称：

  杯[4]芳烃-α-羟基膦酸。谷胱甘肽S-转移酶的合成、立体化学和抑制

  摘要：

  通过相应的单-和二-甲酰基杯芳烃与二烷基钠盐的反应，制备了一系列在大环上缘带有一个或两个α-羟甲基膦酸片段的二丙氧基-、三丙氧基-和四丙氧基杯（4）芳烃。亚磷酸酯或与三烷基（三甲基甲硅烷基）亚磷酸酯，然后酯衍生物的脱烷基化（脱甲硅烷基化）。通过 1 H NMR研究了大环骨架的构象和所得化合物的立体异构形式。发现所得的α-羟甲基膦酸能够在体外抑制谷胱甘肽S-转移酶的活性。

  DOI：

  10.3998/ark.5550190.0013.421
• 作为产物：
  描述：

  杯[4]芳烃 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 11,23-dibromo-25,26,27,28-tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-5,17-dicarbaldehyde
  参考文献：
  名称：

  Highly extended styrylstyrylcalix[4]arene assemblies: synthesis and optical properties

  摘要：

  Novel highly extended, cone-conformed tetrakis-styrylstyryltetrapropoxycalix[4]arenes and bis-styryl-styryltetrapropoxycalix[4]arenes were synthesized by stereoselective Wadsworth-Emmons reactions. Intramolecular chromophoric interaction of these assemblies resulted in changes to optical properties relative to those of the corresponding monomers with fluorescence enhancement being observed for the assemblies end-capped with methylsulfonyl accepters. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00948-5

文献信息

• The synthesis and properties of a calixarene-based ‘sugar bowl’
  作者：Patrick Linnane、Tony D. James、Seiji Shinkai

  DOI：10.1039/c39950001997

  日期：——

  A novel calix-diboronic acid 1 has been synthesised which can detect saccharides at neutral pH in aqueous media; the binding events are sensitively monitored by changes in the fluorescence intensity.

  一种新型的钙克斯-二硼酸1已被合成，该化合物能够在中性pH条件下在水相中检测糖类；结合事件通过荧光强度的变化被灵敏监测。
• Jorgensen, Mikkel; Krebs, Frederik C., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 9, p. 1929 - 1934
  作者：Jorgensen, Mikkel、Krebs, Frederik C.

  DOI：——

  日期：——
• Synthesis and structure of [2-oxo(thioxo)tetrahydropyrimidin-4-yl]calix[4]arenes
  作者：S. G. Vishnevskii、A. B. Drapailo、A. V. Ruban、V. V. Pirozhenko、S. V. Shishkina、O. V. Shishkin、V. I. Kal’chenko

  DOI：10.1134/s1070428014040228

  日期：2014.4

  Cone-shaped di- and tetrapropoxycalix[4]arenes functionalized at the upper rim with one or two 2-oxo(thioxo)tetrahydropyrimidine residues were synthesized by the Biginelli reaction of formylcalixarenes with urea (thiourea) and methyl acetoacetate. The steric structure of the products was studied by NMR and X-ray diffraction. The Biginelli reaction with dipropoxyformylcalixarene was diastereoselective, and it quantitatively produced the corresponding meso form. Tetrapropoxydiformylcalixarenes under analogous conditions gave rise to equimolar mixtures of racemic and meso compounds. The macrocyclic skeleton of the synthesized pyrimidine-containing calixarenes in crystal and in solution has a flattened cone conformation. (5-Methoxycarbonyl-2-oxotetrahydropyrimidin-4-yl)calixarene molecules in crystal undergo self-organization to form infinite chains via repeated inclusion of the methoxy group into the cavity of the neighboring macrocycle. Selforganization of bis(5-methoxycarbonyl-2-oxotetrahydropyrimidin-4-yl)calixarene with formation of analogous chains involves intermolecular hydrogen bonding NH ... O=C.