5,17-diallylcalix[4]arene | 125065-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,17-diallylcalix[4]arene
• 英文别名: 5,17-Diallyl-25,26,27,28-tetrahydroxycalix[4]arene；5,17-bis(prop-2-enyl)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-dodecaene-25,26,27,28-tetrol
• CAS: 125065-75-0
• 化学式: C₃₄H₃₂O₄
• 分子量: 504.626
• InChiKey: AHFWUMOLHHUWBU-UHFFFAOYSA-N

物化性质

• 熔点：
  233-235 °C
• 沸点：
  654.5±55.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,17-diallylcalix[4]arene 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Synthesis of Bridged, Multifunctional Calixarenes via Ring Closing Metathesis

  摘要：

  Ring-closing metathesis catalyzed by RuCl2(CHPh)(PCy3)(2) has been used to synthesize calix[4]arenes in cane and 1,3-alternate conformations with upper and lower rim alkenyl bridges. Ester, methoxy, and hydroxy groups have been used to probe the effect of substituents on the mode of metathesis. With some substrates, intermolecular metathesis competes with the intramolecular process leading to oligocalix[4]arenes. X-ray diffraction has been used to reveal the molecular structures of two single-bridged calix[4]arenes and of a double-bridged calix[4]arene.

  DOI：

  10.1021/jo970887q
• 作为产物：
  描述：

  25,27-dihydroxy-26,28-bis(prop-2-en-1-yloxy)calix[4]arene 以 various solvent(s) 为溶剂， 生成 5,17-diallylcalix[4]arene
  参考文献：
  名称：

  杯[4]芳烃在上缘的选择性功能化

  摘要：

  描述了通过转移功能和在苯酚环对位的选择性取代在上边缘对杯[4]芳烃进行选择性径向官能化的方法。描述了26,28-二甲氧基-11,23-二硝基杯[4]芳烃的晶体结构。

  DOI：

  10.1016/s0040-4039(00)99097-x

文献信息

• Capping the upper and lower rims of calix[4]arenes by aryl dinitrile oxide reactions
  作者：Ya-Jiun Shiao、Pei-Chen Chiang、Annamalai Senthilvelan、Ming-Tsung Tsai、Gene-Hsiang Lee、Wen-Sheng Chung

  DOI：10.1016/j.tetlet.2006.09.070

  日期：2006.11

  1,3-Dipolar cycloadditions of upper- and lower-rim diallylcalix[4]arenes (1 and 3) with aryl dinitrile oxides provide a unique and efficient way of capping the calix[4]arenes. When dinitrile oxides reacted with 5-allylcalix[4]arene 7, they underwent a 1,3-dipolar cycloaddition on one side and an electrophilic substitution on the other side, which led to a novel type of asymmetric calix[4]arenes (9

  上缘和下缘二烯丙基杯[4]芳烃（1和3）的1，3-偶极环加成与芳基二腈氧化物提供了一种独特且有效的方式来盖住杯[4]芳烃。当二腈氧化物与5-烯丙基杯[4]芳烃7反应时，它们的一侧发生1,3-偶极环加成反应，另一侧发生亲电取代，这导致了新型的不对称杯[4]芳烃（9和12）。
• Calix[4]arenes with a Lid in their Upper Rims: 1,3-Dipolar Cycloaddition Reactions of Benzonitrile Oxides with 5-Allyl-, 5,11-Dially- and 5,17-Diallylcalix[4]arenes
  作者：Chun-Mei Shu、Wei-Ling Lin、Gene-Hsiang Lee、Shie-Ming Peng、Wen-Sheng Chung

  DOI：10.1002/jccs.200000020

  日期：2000.2

  The upper rim substituted mono- and diisoxazolinomethylcalix[4]arenes 9-23 are synthesized in good yields from 1,3-dipolar cycloaddition reactions of papa-substituted phenyl nitrileoxides with 5-allyl-, 5,11-diallyl-and 5,17-diallycalix[4]arenes 5-7; the structures of 9-23 are consistent with a ‘cone’ conformation and the ‘vase-with-a-lid’ structure of 11 was confirmed by a single-crystal x-ray analysis

  上环取代的单和二异恶唑啉基甲基杯[4]芳烃 9-23 由木瓜取代的苯腈氧化物与 5-烯丙基-、5,11-二烯丙基-和 5,17 的 1,3-偶极环加成反应合成，收率良好-diallycalix[4]芳烃 5-7；9-23 的结构与“锥形”构象一致，11 的“带盖花瓶”结构通过单晶 X 射线分析得到证实。初步结果表明，单异恶唑啉甲基杯[4]芳烃可以与铵阳离子形成包合物。
• Glycoside-Clustering Round Calixarenes toward the Development of Multivalent Carbohydrate Ligands. Synthesis and Conformational Analysis of Calix[4]arene <i>O</i>- and <i>C</i>-Glycoconjugates
  作者：Alessandro Dondoni、Martin Kleban、Xubo Hu、Alberto Marra、Harold D. Banks

  DOI：10.1021/jo020178z

  日期：2002.7.1

  and C-glycosyl calixarenes (calixsugars) have been prepared by tethering carbohydrate moieties to a tetrapropoxycalix[4]arene scaffold through alkyl chains. Two methodologies have been employed. One consisted of the stereoselective multiple glycosylation of upper rim calix[4]arene polyols leading to calix-O-glycosides; the other involved a multiple Wittig olefination of upper rim calix[4]arene-derived

  通过将碳水化合物部分通过烷基链束缚到四丙氧基杯[4]芳烃骨架上，制备了双-和四-O-和C-糖基杯芳烃（杯糖）。已经采用了两种方法。一种是由上边缘杯[4]芳烃多元醇的立体选择性多重糖基化反应而形成杯-O-糖苷。另一种涉及通过使用糖磷烷将上边缘杯[4]芳烃衍生的多醛进行多次维蒂希烯烃化反应，并还原烯烃双键，得到杯-C-糖苷。双糖基化产物的NMR光谱和NOE实验表明，带有糖保护残基的化合物优先以扁平圆锥排列形式（远构象）存在于溶液中，而脱保护的衍生物则采用紧密构象。
• Diallylbis(arylazo)calix[4]arenes: the syntheses of calix[4]arenes with two different para-substituents
  作者：Chun-mei Shu、Tai-sheng Yuan、Ming-chung Ku、Zong-chia Ho、Wen-chin Liu、Fa-shin Tang、Lee-gin Lin

  DOI：10.1016/0040-4020(96)00512-1

  日期：1996.7

  The diazonium coupling between two kinds of p-diallylcalix[4]arenes (3 and 4) and p-substituted benzenediazonium salts yielded calix[4]arenes with two different substituents on their para-position. The synthesis and the 1H-NMR spectral characteristic features of the two p-diallylcalix[4]arenes and their arylazo derivatives are discussed.

  两种对二烯丙基杯[4]芳烃（3和4）与对位取代的苯重氮盐之间的重氮偶合反应产生了杯[4]芳烃，其对位带有两个不同的取代基。讨论了两个对二烯丙基杯[4]芳烃及其芳基偶氮衍生物的合成及1 H-NMR光谱特征。
• Synthesis of bridged and oligocalix[4]arenes via ruthenium-catalysed ring closing metathesis
  作者：M. Anthony McKervey、Miguel Pitarch

  DOI：10.1039/cc9960001689

  日期：——

  Ruthenium-catalysed metathesis of calix[4]arenes with alkenyl substituents on the upper or lower rims leads efficiently to singly- or doubly-bridged calix[4]arenes and oligocalix[4]arenes.

  在钌催化下，上缘或下缘带有烯基取代基的钙[4]炔能有效地发生偏析反应，生成单桥或双桥钙[4]炔和低聚钙[4]炔。