Ketocalixarenes: Versatile yet still Unexplored Macrocycles

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC
Synlett Pub Date : 2024-08-12 DOI:10.1055/s-0043-1775380
Ori Shalev, Silvio E. Biali
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引用次数: 0

Abstract

Ketocalix[n]arenes can be prepared via oxidation of the methylene groups of protected calix[n]arenes. The presence of carbonyl groups at the bridges alters the preferred conformation and reactivity of the macrocycle and provides an entry point (via nucleophilic additions reactions) to a wide array of methylene-substituted derivatives as well as calix[n]radialenes.

1 Introduction

2 Synthesis of Ketocalix[n]arenes

2.1 Ketocalix[4]arene Derivatives

2.2 Systems Possessing both Carbonyl and Bromomethane Bridges

2.3 Pentaoxoketocalix[5]arene and Hexaoxoketocalix[6]arene Derivatives

2.4 Monooxo- and Dioxoketocalix[6]arenes

3 Conformation of Ketocalixarenes

4 Reactions of Ketocalixarenes

4.1 Alkylation of the OH Groups

4.2 Intramolecular Aromatic Nucleophilic Substitution

4.3 Reduction of the Carbonyl Groups

4.4 Reaction of 5c with PhLi

4.5 Reaction with tert-Butyllithium

5 From Ketocalix[n]arenes to Calix[n]radialenes and Calix[n]rotanes

6 Summary and Outlook

Abstract Image

酮钙烯烃:用途广泛但仍未开发的大环
通过氧化受保护的钙并[n]烯的亚甲基,可以制备酮钙并[n]烯。桥上羰基的存在改变了大环的优选构象和反应活性,并(通过亲核加成反应)为多种亚甲基取代衍生物以及钙并[n]辐射烯提供了切入点。1 引言 2 Ketocalix[n]arenes 的合成 2.1 Ketocalix[4]arene 衍生物 2.2 同时具有羰基和溴甲烷桥的体系 2.3 Pentaoxoketocalix[5]arene 和 Hexaoxoketocalix[6]arene 衍生物 2.4 Monooxo- 和 Dioxoketocalix[6]arenes 3 Ketocalixarenes 的构象 4 Ketocalixarenes 的反应 4.1 OH 基团的烷基化 4.2 分子内芳香族亲核取代 4.3 羰基的还原 4.4 5c 与 PhLi 的反应 4.5 与叔丁基锂的反应 5 从 Ketocalix[n]arenes 到 Calix[n]radialenes 和 Calix[n]rotanes 6 小结与展望
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来源期刊
Synlett
Synlett 化学-有机化学
CiteScore
3.40
自引率
5.00%
发文量
369
审稿时长
1 months
期刊介绍: SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
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