60462-27-3

Usage

Chemical structure

1,4-bis(hydroxymethyl)cubane is a chemical compound with a unique cubane structure and two hydroxymethyl groups attached to the carbon atoms at positions 1 and 4 of the cubane molecule.

Symmetry

It is a highly symmetrical and rigid molecule.

Applications

It has potential applications in medicinal chemistry and materials science due to its unique structure.

Functionalization

The hydroxymethyl groups provide reactive sites for further functionalization.

Versatility

1,4-bis(hydroxymethyl)cubane is a versatile building block for the synthesis of various organic compounds.

High-energy density material

It has been studied for its potential as a high-energy density material.

Propellant or fuel additive

Its molecular structure may contribute to its use as a propellant or fuel additive.

Electronic or mechanical properties

The rigid and compact structure of 1,4-bis(hydroxymethyl)cubane makes it a promising candidate for the development of new materials with specific electronic or mechanical properties.

Upstream product

• 29412-62-2 cubane-1,4-dicarboxylic acid dimethyl ester 

Downstream Products

• 163332-89-6 cubane-1,4-dicarboxaldehyde 

Relevant academic research and scientific papers

Cubane derivatives: 3.* synthesis and molecular structure of 1,4-bis(hydroxymethyl)cubane

An efficient procedure for the preparation of 1,4-bis(hydroxymethyl)cubane by reduction of cubane-1,4-dicarboxylic acid or its dimethyl ester with aluminum hydride was developed. The molecular structure of 1,4-bis(hydroxymethyl)cubane was established by X-ray diffraction analysis.

Building siRNAs with Cubes: Synthesis and Evaluation of Cubane-Modified siRNAs

Cubane molecules hold great potential for medicinal chemistry applications due to their inherent stability and low toxicity. In this study, we report the synthesis of a cubane derivative phosphoramidite for the incorporation of cubane into small interfering RNAs (siRNAs). Synthetic siRNAs rely on chemical modifications to improve their pharmacokinetic profiles. However, they are still able to mediate sequence-specific gene silencing via the endogenous RNA interference pathway. We designed a library of siRNAs bearing cubane at different positions within the sense and antisense strands. All siRNAs showed excellent gene-silencing activity, with IC50 values ranging from 45.4 to 305 pM. Incorporating the cubane modification in both the sense and antisense strand led to viable duplexes with good biological activity. To the best of our knowledge, this is the first report of siRNAs bearing a cubane derivative within the backbone.

Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations

The scope and limitations of Eaton's rhodium(I)-catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigated in the context of functional group tolerability, multiple substitution modes and the ability of cubane-alcohols to undergo one-pot tandem Ley–Griffith Wittig reactions in the absence of a transition metal catalyst.

Cubane Arrives on the Cucurbituril Scene

Cubane, an intriguing chemical curiosity first studied in the early 1960s, has become a valuable structural motif and has recently been involved in the structures of a great number of prospective compounds. The first dicationic supramolecular guest 5 is prepared and derived from a 1,4-disubstituted cubane moiety, and its binding behavior toward cucurbit[n]urils (CBn) and cyclodextrins (CD) is studied. The bisimidazolium salt 5 forms 1:1 inclusion complexes with CB7, CB8, and β-CD with the respective association constants (6.7 ± 0.5) × 1011 M-1, (1.5 ± 0.2) × 109 M-1, and 2 M-1 in water. The solid-state structures of the 5@CB7 and 5@CB8 complexes are also reported.

The preparation and fate of cubylcarbinyl radicals

The cubylcarbinyl radical has been generated from cubylcarbinyl bromide and from the N-hydroxy-2-pyridinethaione ester of cubylacetic acid under various conditions favoring hydrogen-atom transfer to the radical. Only when selenophenol in high concentration is used as the hydrogen donor is any methylcubane formed. Otherwise the cubylcarbinyl radical rearranges. There is no evidence of a 1,2-shift into the homocubyl system. Instead, one, two, or three bonds of the cubane nucleus cleave, leading to a variety of olefinic products. For the most part, these have been characterized. A mechanistic scheme accounting for their formation is presented; sequential σ-bond breaking occurs regioselectively, favoring processes in which there is good overlap between the radical orbital and that of the breaking bond. The distribution of products is shown to depend qualitatively on the time the radical intermediates are let live, that is, on the concentration and effectiveness of the hydrogen atom transfer agent. From product distributions, the rate constant for ring cleavage of cubylcarbinyl radical is calculated to be at least 2 × 1010 s-1, substantially greater than that of any radical derived to date from a saturated hydrocarbon system. Methodology is given for the synthesis of cubylcarbinol, cubylacetic acid, 1,4-bis(hydroxymethyl)cubane, methylcubane, and a variety of other new cabane compounds.