58920-80-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4318, 1971 DOI: 10.1021/ja00746a052

InChI:InChI=1/C9H13NO2/c1-12-8(11)9(7-10)5-3-2-4-6-9/h2-6H2,1H3

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 105-34-0 methyl 2-cyanoacetate 
• 766-05-2 cyclohexane carbonitrile 
• 17640-15-2 methyl cyanoformate 
• 1510799-28-6 1-(pyridin-2-ylthio)cyclohexanecarbonitrile 
• 1453071-06-1 1-((2-methoxyphenyl)sulfinyl)cyclohexanecarbonitrile 
• 1360557-39-6 1-(phenylsulfinyl)cyclohexanecarbonitrile 
• 3196-23-4 methyl 1-bromocyclohexanecarboxylate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 108-94-1 cyclohexanone 
• 61827-29-0 1-(1-Cyanocyclohexyl)-2-carbomethoxyhydrazine 
• 676132-35-7 1-bromocyclohexane-1-carbonitrile 
• 33670-04-1 Methyl N-(1-cyanocyclohexyl)-diazoformiat 

Downstream Products

• 99092-04-3 methyl 1-(aminomethyl)cyclohexanecarboxylate 
• 227203-35-2 trans aminomethylcyclohexanecarboxylic acid 
• 220145-20-0 methyl 1-(<<(tert-butoxy)carbonyl>amino>methyl)cyclohexane-1-carboxylate 
• 204514-23-8 1-(<<(tert-butoxy)carbonyl>amino>methyl)cyclohexane-1-carboxylic acid 
• 220145-23-3 Boc-β^2,2-HAc6c-β^2,2-HAc6c-OMe 
• 220145-27-7 Boc-β^2,2-HAc6c-β^2,2-HAc6c-β^2,2-HAc6c-OH 
• 220145-26-6 Boc-β^2,2-HAc6c-β^2,2-HAc6c-β^2,2-HAc6c-OMe 
• 2041-57-8 (1-(aminomethyl)cyclohexyl)methanol 
• 1420477-37-7 Boc-Aib-β^2,2Ac₆c-OMe 

Relevant academic research and scientific papers

Sulfone–Metal Exchange and Alkylation of Sulfonylnitriles

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Chemoselective Alkylations with N- and C-Metalated Nitriles

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The structural characterization of folded peptides containing the conformationally constrained β-amino acid residue β 2,2Ac6c

Backbone alkylation has been shown to result in a dramatic reduction in the conformational space that is sterically accessible to α-amino acid residues in peptides. By extension, the presence of geminal dialkyl substituents at backbone atoms also restricts available conformational space for β and γ residues. Five peptides containing the achiral β2,2- disubstituted β-amino acid residue, 1-(aminomethyl)cyclohexanecarboxylic acid (β2,2Ac6c), have been structurally characterized in crystals by X-ray diffraction. The tripeptide Boc-Aib-β 2,2Ac6c-Aib-OMe (1) adopts a novel fold stabilized by two intramolecular H-bonds (C11 and C9) of opposite directionality. The tetrapeptide Boc-[Aib-β2,2Ac 6c]2-OMe (2) and pentapeptide Boc-[Aib-β 2,2Ac6c]2-Aib-OMe (3) form short stretches of a hybrid αβ C11 helix stabilized by two and three intramolecular H-bonds, respectively. The structure of the dipeptide Boc-Aib-β2,2Ac6c-OMe (5) does not reveal any intramolecular H-bond. The aggregation pattern in the crystal provides an example of an extended conformation of the β2,2Ac6c residue, forming a 'polar sheet' like H-bond. The protected derivative Ac-β2,2Ac6c-NHMe (4) adopts a locally folded gauche conformation about the Cβi?￡?C α bonds (θ=-55.7°). Of the seven examples of β2,2Ac6c residues reported here, six adopt gauche conformations, a feature which promotes local folding when incorporated into peptides. A comparison between the conformational properties of β2,2Ac6c and β3,3Ac6c residues, in peptides, is presented. Backbone torsional parameters of H-bonded αβ/βα turns are derived from the structures presented in this study and earlier reports. Copyright

Nitrile alkylations through sulfinyl-metal exchange

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(Chemical Equation Presented) α-Halonitriles react with alkyllithium, organomagnesium, and lithium dimethylcuprate reagents generating reactive, metalated nitriles. The rapid halogen-metal exchange with alkyllithium and Grignard reagents allows selective exchange in the presence of reactive carbonyl electrophiles, including aldehydes, providing a high-yielding alkylation protocol. Lithiated and magnesiated nitriles react with propargyl bromide by SN2 displacement whereas organocopper nitriles react by S N2′ displacement, correlating with the formation of a C-metalated nitrile.