Preparations and properties of caged polycyclic systems. 1. Pentacyclo[5.3.0.02,5.03,9.04,8]decane and pentacyclo[4.3.0.02,5.03,8.04,7]nonane derivatives
About: This article is published in Journal of Organic Chemistry.The article was published on 1970-11-01. It has received 95 citations till now. The article focuses on the topics: Decane & Nonane.
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TL;DR: A family of 4-substituted 1-cubanecarboxylic acids have been synthesized and their X-ray crystal structures analyzed as discussed by the authors, and the rare syn-anti O−H−O catemer 6 is a recurring pattern in this series of compounds.
Abstract: A family of 4-substituted-1-cubanecarboxylic acids have been synthesized and their X-ray crystal structures analyzed. The rare syn-anti O−H···O catemer 6 is a recurring pattern in this series of compounds. Catemer 6 is observed in the crystal structures of 4-chloro-1-cubanecarboxylic acid (10), 4-bromo-1-cubanecarboxylic acid (11), 4-iodo-1-cubanecarboxylic acid (12), and 4-(methoxycarbonyl)-1-cubanecarboxylic acid (13). The ready occurrence of catemer 6 in this family is ascribed to its stabilization by auxiliary C−H···O hydrogen bonds formed by the relatively acidic cubyl C−H groups. The frequency of occurrence of 6 also facilitates its definition as a useful supramolecular synthon. As is true in many catemers, the formation of 6 is sensitive to steric factors. Therefore, the robustness of this synthon may be assessed by analyzing the crystal structures of molecules wherein the 4-substituent is too small (R = H, 14), too large (R = Ph, 15), or has a specific hydrogen bonding preference of its own (R = C...
239 citations
TL;DR: This paper presents a meta-analyses of the chiral stationary phase of Na6(CO3)(SO4)2, which shows clear patterns in the response of the immune system to Na2CO3 and also investigates the role of “chiral reprograming” in the formation of Na2SO4.
Abstract: Kyle F. Biegasiewicz,† Justin R. Griffiths,‡ G. Paul Savage, John Tsanaktsidis, and Ronny Priefer* †Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, United States ‡Department of Chemistry, University at Buffalo, Buffalo, New York 14260-1660, United States Ian Wark Laboratory, CSIRO Manufacturing Flagship, Bayview Avenue, Clayton, Victoria 3168, Australia College of Pharmacy, Western New England University, Springfield, Massachusetts 01119, United States
124 citations
TL;DR: This Review article focuses on covalently linked, nonconjugated linear arrangements and discusses the physical and chemical properties and differences of individual linkers, as well as their application in material and medicinal sciences.
Abstract: Nonconjugated hydrocarbons, like bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, triptycene, and cubane are a unique class of rigid linkers. Due to their similarity in size and shape they are useful mimics of classic benzene moieties in drugs, so-called bioisosteres. Moreover, they also fulfill an important role in material sciences as linear linkers, in order to arrange various functionalities in a defined spatial manner. In this Review article, recent developments and usages of these special, rectilinear systems are discussed. Furthermore, we focus on covalently linked, nonconjugated linear arrangements and discuss the physical and chemical properties and differences of individual linkers, as well as their application in material and medicinal sciences.
118 citations
TL;DR: This Perspective describes synthetic methodology for accessing a range of functionalized cubanes and their applications in pharmaceuticals and provides some perspectives on challenges and future directions in the advancement of this field.
Abstract: Cubane is a highly strained saturated hydrocarbon system that has historically been of interest in theoretical organic chemistry. More recently it has become a molecule of interest for biological applications due to its inherent stability and limited toxicity. Of greater significance is the ability to potentially functionalize cubane at each of its carbon atoms, providing complex biologically active molecules with unique spatial arrangements for probing active sites. These characteristics have led to an increased use of cubane in pharmaceutically relevant molecules. In this Perspective we describe synthetic methodology for accessing a range of functionalized cubanes and their applications in pharmaceuticals. We also provide some perspectives on challenges and future directions in the advancement of this field.
73 citations
TL;DR: The first synthesis of pentaprismane, hexacyclo[4.4.0.0 2,5.0 3,9.0 4,8.0 7,10 ]decane, is presented in this article.
67 citations