25,27-bis[(1-((R)-(α-pyrrolidinylbenzyl))naphthalen-2-yloxy)propoxy]-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene | 1266715-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 25,27-bis[(1-((R)-(α-pyrrolidinylbenzyl))naphthalen-2-yloxy)propoxy]-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene
• 英文别名: 5,11,17,23-tetratert-butyl-26,28-bis[3-[1-[(R)-phenyl(pyrrolidin-1-yl)methyl]naphthalen-2-yl]oxypropoxy]pentacyclo[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-25,27-diol
• CAS: 1266715-35-8
• 化学式: C₉₂H₁₀₆N₂O₆
• 分子量: 1335.86
• InChiKey: AESAAQAVZITIBA-KARIZSNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.2
• 重原子数：
  100
• 可旋转键数：
  22
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,27-di(2-bromopropyl)-26,28-dihydroxycalix[4]arene 、 (R)-1-(phenyl(pyrrolidin-1-yl)methyl)naphthalen-2-ol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到25,27-bis[(1-((R)-(α-pyrrolidinylbenzyl))naphthalen-2-yloxy)propoxy]-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene
  参考文献：
  名称：

  带有氨基萘部分的手性杯[4]芳烃的合成及其在羧酸的对映体识别中的应用†

  摘要：

  制备了两个在下部边缘用手性氨基萘酚官能化的武装手性杯[4]芳烃8-16，并通过FTIR，1 H和13 C，DEPT和COZY NMR光谱学和元素分析对这些受体的结构进行了表征。通过1 H NMR和UV / Vis光谱研究了这些受体与各种羧酸的对映选择性识别。受体对外消旋物质的对映异构体表现出不同的手性识别能力，并在宿主和客体之间形成2：1或1：1的复合物。还证明手性杯[4]芳烃9和16 可以用作手性NMR溶剂来确定对映体的纯度 扁桃酸。

  DOI：

  10.1039/c0ob00399a

文献信息

• Chiral calix[4]arenes bearing aminonaphthol moieties as membrane carriers for amino acid methyl esters and mandelic acid
  作者：Mustafa Durmaz、Selahattin Bozkurt、Hayriye Nevin Naziroglu、Mustafa Yilmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2011.04.019

  日期：2011.4

  Chiral calix[4]arene derivatives functionalized at the lower rim with chiral aminonaphthol units have been prepared. The structures of these receptors were characterized by a combination of (1)H NMR, (13)C NMR, FTIR and elemental analysis. The transport of amino acid derivatives (phenylglycine, phenylalanine and tryptophan methyl ester hydrochlorides) and mandelic acid were studied through a bulk liquid membrane in the presence of chiral calix[4]arene derivatives. The transport rate and enantioselectivity of the amino acid esters studied depended mainly upon the structure of the chiral receptors. The influence of calixarene and amino acid ester structures upon transport through a liquid membrane is discussed. The receptors with hydrogen bonding sites and aromatic groups showed considerable higher transport rates and stereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of chiral calix[4]arenes bearing aminonaphthol moieties and their use in the enantiomeric recognition of carboxylic acids
  作者：Mustafa Durmaz、Mustafa Yilmaz、Abdulkadir Sirit

  DOI：10.1039/c0ob00399a

  日期：——

  exhibited different chiral recognition abilities towards the enantiomers of racemic materials and formed 2 : 1 or 1 : 1 complexes between host and guest. It was also demonstrated that chiral calix[4]arenes 9 and 16 could be used as chiral NMR solvating agents to determine the enantiomeric purity of mandelic acid.

  制备了两个在下部边缘用手性氨基萘酚官能化的武装手性杯[4]芳烃8-16，并通过FTIR，1 H和13 C，DEPT和COZY NMR光谱学和元素分析对这些受体的结构进行了表征。通过1 H NMR和UV / Vis光谱研究了这些受体与各种羧酸的对映选择性识别。受体对外消旋物质的对映异构体表现出不同的手性识别能力，并在宿主和客体之间形成2：1或1：1的复合物。还证明手性杯[4]芳烃9和16 可以用作手性NMR溶剂来确定对映体的纯度 扁桃酸。