60462-19-3

Usage

Uses

Used in Pharmaceutical Synthesis:
METHYL 4-HYDROXYMETHYLCUBANECARBOXYLATE is used as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure and properties make it a valuable building block for creating new and effective drugs.
Used in Organic Chemistry Research:
METHYL 4-HYDROXYMETHYLCUBANECARBOXYLATE is used as a building block in the synthesis of novel organic molecules with unique chemical properties. Its potential applications in drug development and materials science make it an important compound for research and innovation in the field of organic chemistry.
Used in Drug Development:
METHYL 4-HYDROXYMETHYLCUBANECARBOXYLATE is used as a starting material for the development of new drugs. Its unique structure and properties allow for the creation of innovative and effective pharmaceuticals that can address various medical needs.
Used in Materials Science:
METHYL 4-HYDROXYMETHYLCUBANECARBOXYLATE is used in the development of new materials with unique properties. Its potential applications in this field make it an important compound for research and innovation in materials science.

InChI:InChI=1/C11H12O3/c1-14-9(13)11-6-3-7(11)5-8(11)4(6)10(3,5)2-12/h3-8,12H,2H2,1H3

Upstream product

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

Downstream Products

• 1431475-02-3 (4-methoxycarbonyl)cubylmethyl 2-nitrobenzoate 
• 1431475-01-2 (4-methoxycarbonyl)cubylmethyl 3-nitrobenzoate 
• 1431475-00-1 (4-methoxycarbonyl)cubylmethyl p-nitrophenoxide 
• 1350821-91-8 4-(fluoromethyl)-N-(2-(4-(2-hydroxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)cubane-1-carboxamide 
• 1350821-87-2 4-(fluoromethyl)-N-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)cubane-1-carboxamide 
• 211635-37-9 4-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-cubane-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

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.

Determining the necessity of phenyl ring π-character in warfarin

Despite the difficulty in administering a safe dose regimen and reports of emerging resistance, warfarin (1) remains the most widely-used oral anticoagulant for the prevention and treatment of thrombosis in humans globally. Systematic substitution of the warfarin phenyl ring with either 1,3,5,7-cyclooctatetraene (COT) (2), cubane (3), cyclohexane (4) or cyclooctane (5) and subsequent evaluation against the target enzyme, vitamin K epoxide reductase (VKOR), facilitated interrogation of both steric and electronic properties of the phenyl pharmacophore. The tolerance of VKOR to further functional group modification (carboxylate 14, PTAD adduct 15) was also investigated. The results demonstrate the importance of both annulene conferred π-interactions and ring size in the activity of warfarin.

Cubanes in medicinal chemistry: Synthesis of functionalized building blocks

A collection of novel, pharmaceutically relevant cubane-containing molecules has been prepared from the commercially available cubane-1,4- dimethylester. A range of synthetic methods have been applied to prepare these cubane building blocks with one or two functional handles to allow easy incorporation into existing medicinal chemistry programs.

Hyperconjugation involving strained carbon-carbon bonds. Application of the variable oxygen probe to ester and ether derivatives of cubylmethanol

Application of the variable oxygen probe to derivatives of (4-methoxycarbonyl)cubylmethanol 11 demonstrated a strong response of C-OR bond distance to the electron demand of the OR substituent, consistent with an enhanced σ-donor ability of the strained C-C bonds of cubane. The extent of cubane donor ability was found to be superior to an unstrained donor 13, comparing data extracted from the Cambridge Structural Database (T. W. Cole, Ph.D. Dissertation, University of Chicago, 1966), but weaker than the previously studied cyclopropane donors. Structural evidence is also found for σCC-π*CO interactions in these structures. The Royal Society of Chemistry 2013.

Synthesis and preliminary evaluation of (S)-2-(4'-carboxycubyl)glycine, a new selective mGluR1 antagonist

The synthesis and the pharmacological evaluation at metabotropic glutamate receptors of S-2-(4'-carboxy-cubyl)glycine (ACUDA, 9) are described. S-2-(4'-Carboxy-cubyl)glycine is a structurally novel group I selective antagonist for mGluR1 subtype.