5,11,17,23-tetraformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene | 136991-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetraformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene
• 英文别名: 5,11,17,23-Tetraformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene；5,11,17,23-tetraformyl-25,26,27,28-tetrakis-(2-ethoxyethyl)calix[4]arene；25,26,27,28-Tetrakis(2-ethoxyethoxy)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-5,11,17,23-tetracarbaldehyde
• CAS: 136991-58-7
• 化学式: C₄₈H₅₆O₁₂
• 分子量: 824.965
• InChiKey: GRYTXAQJOSHZFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  60
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetraformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5,11,17,23-tetrakis(chloromethyl)-25,26,27,28-tetrakis(ethoxyethoxy)calix<4>arene
  参考文献：
  名称：

  Calix[4]arenes Linked to Multiple Bidentate N-Donors:  Potential Ligands for Synthetic Modeling of Multinuclear Metalloenzymes

  摘要：

  [GRAPHICS]A series of calix[4]arenes incorporating three or four bidentate diamines or pyridylamines attached at the "upper rim" were synthesized via practical protocols. Proof of structure was obtained in one instance by X-ray crystallography. These molecules are designed for general use as ligands for the preparation of multinuclear active site models of metalloenzymes.

  DOI：

  10.1021/ol025715g
• 作为产物：
  描述：

  4-叔丁基苯酚 在 aluminum (III) chloride 、 四氯化钛 、 sodium hydride 、 sodium hydroxide 、 苯酚 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 生成 5,11,17,23-tetraformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene
  参考文献：
  名称：

  Synthesis and evaluation of deep cavity imidazolyl calix[n]arenes

  摘要：

  通过五步合成法（包括预成型钙[n]烯下缘的适当烷基化、上缘的甲酰化以及随后在醋酸铵和冰醋酸存在下与芳基二酮的缩合），从容易获得的起始材料中获得了一系列深腔二苯基咪唑钙[n]烯（4、6、8）。已对获得锥形构型的标题衍生物的优化反应条件以及通过光谱方法（红外光谱、紫外光谱、核磁共振和 FAB 质量）对其进行表征进行了界定。初步研究了合成的咪唑烷基萼片烯对一价金属离子（Li+、Na+、K+、Cs+、Ag+）的选择性识别能力。

  DOI：

  10.1007/s10847-010-9921-2

文献信息

• Selective formylation of calix[4]arenes at the ‘upper rim’ and synthesis of new cavitands
  作者：Arturo Arduini、Giuseppe Manfredi、Andrea Pochini、Anna Rita Sicuri、Rocco Ungaro

  DOI：10.1039/c39910000936

  日期：——

  The direct selective upper rim 1,3-formylation of conformationally rigid calyx[4]arenes is achieved for the first time; the diametrical bis(formyl)calix[4]arene 4 is used as a key intermediate for the synthesis of new cavitands.

  首次实现构象刚性花萼[4]芳烃的直接选择性上边缘1,3-甲酰化；径向双（甲酰基）杯[4]芳烃4被用作合成新空泡分子的关键中间体。
• New calix[4]arenes having electron donating groups at the upper rim as molecular platforms and host molecules
  作者：Arturo Arduini、Leonardo Mirone、Daniela Paganuzzi、Alessandra Pinalli、Andrea Pochini、Andrea Secchi、Rocco Ungaro

  DOI：10.1016/0040-4020(96)00238-4

  日期：1996.4

  a new and general synthetic procedure for the exhaustive and selective introduction of hydroxy groups at the upper rim of calix[4]arenes in the cone conformation is reported. The aldehyde-derivatives of tetraalkoxycalix[4]arenes have been oxidized by Baeyer-Villiger reaction. The introduction of amino and hydroxy groups on calix[4]arene having a rigid cone conformation has been achieved for the first

  报道了一种新的通用合成方法，用于在圆锥构象的杯[4]芳烃的上边缘完全和选择性地引入羟基。四烷氧基杯[4]芳烃的醛衍生物已被Baeyer-Villiger反应氧化。首次实现在具有刚性圆锥构象的杯[4]芳烃上引入氨基和羟基。
• Synthesis of selectively formylated calixarene ethers
  作者：Vandna Arora、H.M Chawla、Anuradha Santra

  DOI：10.1016/s0040-4020(02)00551-3

  日期：2002.7

  By careful choice of a catalyst (TiCl4 or SnCl4) temperature, reaction time and mole ratio of the substrate to dichloromethyl-methylether, it has been possible to obtain new functionalized formylated calix[n]arenes in the cone or partial cone conformation. Optimized general reaction procedures for obtaining mono-, di-, tri- and tetraformylated derivatives of calix[4]arenes as exemplified by formylation of tetramethoxy-, tetrakis(2-ethoxyethoxy)-, bis(ethoxycarbonylmethoxy)- and bis(hexadecyloxy)-calix[4]-arenes have been reported. (C) 2002 Published by Elsevier Science Ltd.
• Direct Regioselective Formylation of Tetraalkoxycalix[4]arenes Fixed in the Cone Conformation and Synthesis of New Cavitands
  作者：Arturo Arduini、Stefano Fanni、Giuseppe Manfredi、Andrea Pochini、Rocco Ungaro、Anna R. Sicuri、Franco Ugozzoli

  DOI：10.1021/jo00110a054

  日期：1995.3

  Regioselectivity of the formylation of tetraalkoxycalix[4]arene fixed in the cone conformation has been studied. Direct, diametrical (1,3) diformylation of calix[4]arenes having four chelating chains at the lower rim has been achieved. Simple tetraalkoxycalix[4]arenes produce a mixture of diametrical (1,3) and proximal (1,2) diformylated products. The (1,3) functionalized compounds have been used for the synthesis of double calix[4]arenes 12a,d linked via the upper rim. The residual mobility of these cone conformers is indicated by the X-ray crystal structure of compound 12d, which shows a flattened cone conformation, and by the reactive behavior of 1,3-bis(hydroxymethyl) derivatives 9a,d which give very distorted 1,3-bridged compounds 11a,d, through an intramolecular cyclization process.
• The first synthesis and characterisation of elusive cone 1,2-diformyl tetralkoxycalix[4]arenes and their derivatives
  作者：Andrea Sartori、Alessandro Casnati、Luigi Mandolini、Francesco Sansone、David N Reinhoudt、Rocco Ungaro

  DOI：10.1016/s0040-4020(03)00808-1

  日期：2003.7

  The synthesis and isolation of elusive tetralkoxycalix[4]arenes 2 in the cone conformation and bearing two formyl groups in proximal (1.2) positions at the upper rim are described for the first time. They were obtained as a mixture with the distal (1,3) regioisomers 3 by optimizing the Gross formylation reaction on the tetralkoxycalix[4]arenes 1. After reduction to the corresponding alcohols, compounds 4 could be isolated and oxidized to 1,2-diformyl (2) and 1,2-diacid (6) tetralkoxycalix[4]arenes. These 1,2-difunctionalized derivatives are useful intermediates for the synthesis of calixarene-based molecular receptors having proximal binding groups. (C) 2003 Elsevier Science Ltd. All rights reserved.