25,27-dihydroxy-26-propoxy-28-(benzyloxy)calix<4>arene | 459141-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,27-dihydroxy-26-propoxy-28-(benzyloxy)calix<4>arene
• 英文别名: 25-benzyloxy-27-propoxy-26,28-dihydroxycalix<4>arene；25,27-dihydroxy-26-phenylmethoxy-28-propoxycalix[4]arene；26-phenylmethoxy-28-propoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-25,27-diol
• CAS: 459141-71-0
• 化学式: C₃₈H₃₆O₄
• 分子量: 556.701
• InChiKey: BKVISMIISDYCIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  25,27-dihydroxy-26-propoxy-28-(benzyloxy)calix<4>arene 在 吡啶 、 氢氧化钾 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 54.0h， 生成 25-allyloxy-26-benzyloxy-27-butoxy-28-propoxycalix<4>arene
  参考文献：
  名称：

  用四种不同的“下缘”取代基合成杯[4]芳烃。

  摘要：

  按照六步序列合成具有四个不同“下边缘”取代基的杯[4]芳烃。使用R（1）X和CH（3）ONa引入第一个烷基（R（1）），然后与R（2）X和K（2）CO（3）反应导致引入第二个3位的烷基（R（2））。苯甲酸酯在1,3-O-二取代阶段被引入作为保护基，并在第三个烷基（R（3））与R（3）X和NaH结合后在碱性条件下被除去。将最终的烷基（R（4））与R（4）X和NaH引入，得到手性标题化合物。

  DOI：

  10.1021/jo981648l
• 作为产物：
  描述：

  25,27-dihydroxy-26,28-dipropoxycalix[4]arene 在 碘代三甲硅烷 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 25,27-dihydroxy-26-propoxy-28-(benzyloxy)calix<4>arene
  参考文献：
  名称：

  Syntheses and optical resolution of calix[4]arenes with molecular asymmetry. Systematic classification of all possible chiral isomers derivable from calix[4]arene

  摘要：

  All possible chiral isomers that can be derived from calix[4]arene by modification of the OH groups were systematically classified. Molecular asymmetry can be generated not only by different substituents but also by conformational isomerism. The numbers of chiral isomers are 24 for tetra-O-substituted calix[4]arenes, 10 for tri-O-substituted calix[4]arenes, 3 for di-O-substituted calix[4]arenes, and 0 for mono-O-substituted calix[4]arenes. This implies that calix[4]arene is a useful building block for the design of novel asymmetric ring structures. In order to demonstrate asymmetry in these chiral calix[4]arenes, we synthesized several tetra-, tri-, and di-O-substituted calix[4]arenes by using the metal template method, the stepwise synthesis method, the protection-deprotection method, etc., which were developed in efforts directed toward regioselective O-alkylation and control of conformational isomerism in calix[4]arenes. Finally, we succeeded in complete optical resolution of chiral calix[4]arenes by an HPLC method using a chiral-packed column or by the formation of diastereomers with the (-)-menthoxyacetyl group. This article thus contains all of the molecular design concepts, syntheses, and optical resolutions of chiral calix[4]arenes.

  DOI：

  10.1021/ja00063a020

文献信息

• Iwamoto Koji, Shimizu Hiroyasu, Araki Koji, Shinkai Seiji, J. Amer. Chem. Soc., 115 (1993) N 10, S 3997-4006
  作者：Iwamoto Koji, Shimizu Hiroyasu, Araki Koji, Shinkai Seiji

  DOI：——

  日期：——
• Highly Selective Optical-Sensing Membranes, Containing Calix[4]arene Chromoionophores, for Pb2+ Ions
  作者：Niels J. van der Veen、Ewa Rozniecka、Léon A. Woldering、Michal Chudy、Jurriaan Huskens、Frank C. J. M. van Veggel、David N. Reinhoudt

  DOI：10.1002/1521-3765(20011119)7:22<4878::aid-chem4878>3.0.co;2-8

  日期：2001.11.19

  Plasticized poly(vinyl chloride) (PVC) optode membranes containing novel calix[4]arene chromoionophores 1 or 2 and one equivalent of a lipophilic anion respond to Pb2+ ions with high selectivity over alkali, alkaline-earth, and other heavy metal ions. This selectivity stems from the combination of ligand specificity and a unique ion exchange scheme that employs both monovalent metal ions and protons as the exchanged ions. Complexation of Pb2+ ions inside the membrane is accompanied by deprotonation of the chromoionophores, which causes a bathochromic shift of the absorption maximum lambda(max). The response to Pb2+ ions is modulated by pH and alkali metal ions in a fashion that is consistent with the proposed ion-exchange mechanism. Of all of the other metal ions tested, only Cs+ and Ag+ produce a color change. However, these monovalent metal ions cause hypsochromic shifts of lambda(max) instead of the bathochromic shift caused by Pb2+, because the chromoionophores remain protonated upon complexation.