5,17-dihydroxymethyl-25,26,27,28-tetra-(1-propoxy)calix[4]arene | 163121-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,17-dihydroxymethyl-25,26,27,28-tetra-(1-propoxy)calix[4]arene
• 英文别名: 5,17-bis(hydroxymethyl)-25,26,27,28-tetrakis(1-propyloxy)calix[4]arene；[17-(Hydroxymethyl)-25,26,27,28-tetrapropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]methanol
• CAS: 163121-51-5；176298-99-0
• 化学式: C₄₂H₅₂O₆
• 分子量: 652.871
• InChiKey: QSCDCAITHZMVHI-UHFFFAOYSA-N

物化性质

• 沸点：
  823.8±65.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,17-dihydroxymethyl-25,26,27,28-tetra-(1-propoxy)calix[4]arene 在 氯化亚砜 、 一水合肼 、 sodium iodide 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 64.0h， 生成 5,17-bis(aminomethyl)-25,26,27,28-tetra-n-propoxy-calix[4]arene
  参考文献：
  名称：

  Casnati, Alessandro; Fochi, Mariacristina; Minari, Patrizia, Gazzetta chimica Italiana, 1996, vol. 126, # 2, p. 99 - 106

  摘要：

  DOI：
• 作为产物：
  描述：

  5,17-dibromo-25,26,27,28-tetra-n-propylcalix[4]arene 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 5,17-dihydroxymethyl-25,26,27,28-tetra-(1-propoxy)calix[4]arene
  参考文献：
  名称：

  由两个杯[4]芳烃组成的新型笼状分子的客体包含特性

  摘要：

  通过将上边缘与两个间隔基连接起来，合成了双斯卡尔克斯[4]芳烃。由于两个碗形杯[4]芳烃中阳离子-π相互作用的协同作用，提高了各种季铵离子的包容能力和选择性。络合和解配过程中非常缓慢的动力学过程以及阳离子客体和抗衡阴离子的分离是由Biscalix [4]芳烃的包封引起的。

  DOI：

  10.1016/s0040-4039(99)02232-7

文献信息

• Calix[4]arenes with 1,2- and 1,3-upper rim tetrathiafulvalene bridges
  作者：Matthias H. Düker、Felix Kutter、Thomas Dülcks、Vladimir A. Azov

  DOI：10.1080/10610278.2013.872245

  日期：2014.8.3

  Herein we report the synthesis of several calix[4]arene derivatives with tetrathiafulvalene bridges at the upper rim. Calix[4]arene-tetrathiafulvalene (TTF) conjugates 4a–d, fixed in cone conformation and comprising two smaller 1,2-bridges, were prepared by cyclisation of tetrakis-chloromethylated calix[4]arene 1 with 2,3-dithiolates of TTFs. Larger calix[4]arene-TTF macrocycles 14 and 15, also in

  在这里，我们报告了几种杯[4]芳烃衍生物的合成，在上缘具有四硫富瓦烯桥。杯[4] 芳烃-四硫富瓦烯 (TTF) 共轭物 4a-d，固定为锥形构象并包含两个较小的 1,2-桥，通过四氯甲基化杯 [4] 芳烃 1 与 2,3-二硫醇盐的环化制备TTF。较大的杯 [4] 芳烃-TTF 大环 14 和 15，同样为锥形构象，包含 1,3-桥，通过用双溴甲基化杯 [4] 环化 TTF 的 2,6- 和 2,7-二硫醇盐合成芳烃 7. 使用循环伏安法表征新杯[4]芳烃-TTF缀合物的氧化还原特性。
• On the ‘livingness’ of a dynamic library of cyclophane formaldehyde acetals incorporating calix[4]arene subunits
  作者：Roberta Cacciapagliaa、Stefano Di Stefanoa、Luigi Mandolinia

  DOI：10.1002/poc.1357

  日期：2008.7

  incorporating calix[4]arene subunits generates a short-lived dynamic library of macrocycles. The side reaction responsible for the loss of ‘livingness’ is the unexpected decomposition of monomeric units into a bridged ether and formaldehyde. A plausible mechanism is suggested, in which the crucial step is the formation of benzyl carbocations strongly stabilized by the alkoxy substituents at the lower rim of the

  酸结合环芳烃[4]芳烃亚基的环烷甲醛缩醛的缩醛缩醛化反应生成了大环化合物的短寿命动态库。导致失去“活性”的副反应是单体单元意外分解为桥连的醚和甲醛。提出了一个可能的机制，其中关键的步骤是在杯[4]芳烃部分的较低边缘上形成烷氧基取代基，从而稳定地稳定苄基碳阳离子。版权所有©2008 John Wiley＆Sons，Ltd.
• Synthesis of a rhodium(<scp>iii</scp>) dinitrogen complex using a calix[4]arene-based diphosphine ligand
  作者：Jack Emerson-King、Sudip Pan、Matthew R. Gyton、Ralf Tonner-Zech、Adrian B. Chaplin

  DOI：10.1039/d2cc06837k

  日期：——

  The synthesis and characterisation of the rhodium(III) dinitrogen complex [Rh(2,2′-biphenyl)(CxP2)(N2)]+ are described, where CxP2 is a trans-spanning calix[4]arene-based diphosphine and the dinitrogen ligand is projected into the cavity of the macrocycle.

  描述了铑 ( III ) 二氮络合物 [Rh(2,2'-联苯)(CxP 2 )(N 2 )] +的合成和表征，其中 CxP 2是反式跨杯[4]芳烃基双膦和二氮配体投射到大环的空腔中。
• Synthesis and Properties ofO-Glycosyl Calix[4]Arenes (Calixsugars)
  作者：Alessandro Dondoni、Alberto Marra、Marie-Christine Scherrmann、Alessandro Casnati、Francesco Sansone、Rocco Ungaro

  DOI：10.1002/chem.19970031108

  日期：1997.11

  AbstractModelO‐glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate‐containing calixarene derivatives named calixsugars. One or two sugar moieties (D‐mannofuranose and D‐glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]arenes bearing two or four hydroxymethyl groups at the upper rim were coupled with perbenzoylated thioethyl D‐galactoside and D‐lactoside in the presence of the thiophilic promoter copper(III) triflate. In this way β‐linked bis‐ and tetrakis‐O‐galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For theO‐lactosyl derivatives only the bis‐substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3‐hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose‐containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.
• 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.