Synthesis of 4-bromocubane-1-carbaldehyde

Шастин, А. В.; Захаров, В. В.; Bugaeva, G. P.; Erëmenko, L. T.; Романова, Л. Б.; Lagodzinskaya, G. V.; Александров, Г. Г.; Еременко, И. Л.

doi:10.1007/s11172-006-0416-7

Cited by 4 publications

(4 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several 4‐bromo‐cubane structures, with alternate substitution patterns and size of the substituents, have been deposited to the CCDC over the past few years. The structure of 4‐bromocubane‐1‐carbaldehyde ( 49 ) exhibits a linear stacking pattern with the cubane scaffolds in line with each other (Figure S22) . Unfortunately, the structure is highly disordered, with the bromine and aldehyde being modeled over each other in multiple parts, and hydrogen atoms have not been assigned in the deposited structure.…”

Section: Resultsmentioning

confidence: 99%

“…The structure of 4-bromocubane-1-carbaldehyde (49)e xhibitsalinear stacking pattern with the cubanes caffolds in line with each other (Figure S22). [24] Unfortunately,t he structure is highly disordered, with the bromine and aldehyde being modeled over each other in multiple parts, and hydrogen atoms have not been assigned in the deposited structure. Therefore, this linear stacking can only indicatet he potential interactions between the cubanes caffolds.…”

Section: Halogensmentioning

confidence: 99%

See 1 more Smart Citation

Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

Flanagan

Bernhard

Plunkett

2019

Chemistry A European J

View full text Add to dashboard Cite

Previous studies by Desiraju and co‐workers have implicated the acidic hydrogen atoms of cubane as a support network for hydrogen bonding groups. Herein we report a detailed structural analysis of all currently available 1,4‐disubstituted cubane structures with an emphasis on how the cubane scaffold interacts in its solid‐state environment. In this regard, the interactions between the cubane hydrogen atoms and acids, ester, halogens, ethynyl, nitrogenous groups, and other cubane scaffolds were cataloged. The goal of this study was to investigate the potential of cubane as a substitute for phenyl. This could be achieved by analyzing all contacts that are directed by the cubane hydrogen atoms in the X‐ray crystal structures. As a result, we have established several new cubane interaction profiles, such as the catemer formation seen in esters, the preferences of halogen–hydrogen contacts over direct halogen bonding, and the stabilizing effects caused by the cubane hydrogen atoms interacting with ethynyl groups. These interaction profiles can then be used as a guide for designing cubane bioisosteres of known materials and drugs containing phenyl moieties.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Halogensmentioning

confidence: 99%

Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

Flanagan

Bernhard

Plunkett

2019

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Iodocubane was synthesized by Eaton’s procedures from appropriate precursors. Methyl 1-bromocubanyl-4-carboxylate and its precursors were synthesized as described by Klunder and Zwanenburg and converted into 2 through standard methodologies .…”

Section: Methodsmentioning

confidence: 99%

“…Methyl 1-bromocubanyl-4carboxylate and its precursors were synthesized as described by Klunder and Zwanenburg 26 and converted into 2 through standard methodologies. 43 1-Bromo-4-iodocubane was synthesized via Moriarty et al process. 44 All compounds and intermediates had analytical data consistent with literature values (see Supporting Information for further information).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Highly Strained Tertiary sp³ Scaffolds: Synthesis of Functionalized Cubanes and Exploration of Their Reactivity under Pd(II) Catalysis

et al. 2015

View full text Add to dashboard Cite

A series of chemically distinct, highly strained, activated cubane scaffolds was synthesized through optimization of the metal-halogen exchange reactions of iodinated cubane derivatives. This included the first reported successful attachment of both boron and phosphorous; key elements in potential transition metal-catalyzed cross coupling reactions; on the cubane scaffold. Additionally, Zn, Sn, Si, S and various C-based systems were also attached in a high-yielding, one-pot reaction from readily available precursors. A comprehensive program investigating the reactivity of these tertiary cubane nucleophiles towards Suzuki-Miyaura, Negishi and Stille cross-coupling methods, never previously reported with the cubane scaffold; is also described, but proved unsuccessful.

show abstract

Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

2009

View full text Add to dashboard Cite

The discovery in 1959 of stable nitroxide‐based free radicals such as the prototypical 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) led to their use as electron spin resonance (ESR) spin labels in chemistry, biomedicine, and materials science. These nitroxides are prepared by the oxidation of secondary amines that contain no hydrogen atoms on the alpha‐carbons. The unique redox properties of nitroxides enable their use as oxidants in organic synthesis. The varied preparation and uses of oxoammonium salts as stoichiometric oxidants for alcohols are one subject of this review. Oxoammonium ions as oxidants for alcohols have a number of advantages, for example, the method is heavy‐metal free and some of the reactions can be performed in water or aqueous mixtures. A few side reactions are associated with these oxidations. The most serious is the fast reaction of the oxoammonium ion with free amines The several ways these oxidation reactions can be carried out are discussed in detail. They are: Oxidations using stoichimetric quantities of preformed oxoammonium salts carried out in either acidic, neutral, or basic conditions; reactions in which stoichiometric quantities of oxoammonium salts are generated in situ by disproportionation of a nitroxide in the presence of a strong acid; nitroxide‐catalyzed oxidations using a secondary oxidant; efficient nitroxide‐catalyzed oxidations of primary alcohols to carboxylic acids; and oxidations of primary alcohols or hemiacetals that can lead to lactones.

show abstract

Synthesis of 4-bromocubane-1-carbaldehyde

Cited by 4 publications

References 9 publications

Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

Highly Strained Tertiary sp³ Scaffolds: Synthesis of Functionalized Cubanes and Exploration of Their Reactivity under Pd(II) Catalysis

Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

Contact Info

Product

Resources

About

Synthesis of 4-bromocubane-1-carbaldehyde

Cited by 4 publications

References 9 publications

Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

Highly Strained Tertiary sp3 Scaffolds: Synthesis of Functionalized Cubanes and Exploration of Their Reactivity under Pd(II) Catalysis

Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

Contact Info

Product

Resources

About

Highly Strained Tertiary sp³ Scaffolds: Synthesis of Functionalized Cubanes and Exploration of Their Reactivity under Pd(II) Catalysis