135362-75-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-2-Hydroxy-2-methyl-heptanitrile is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures that can exhibit therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, (R)-2-Hydroxy-2-methyl-heptanitrile serves as a key component in the creation of compounds designed to protect crops and enhance agricultural productivity, leveraging its reactive nature to form stable and effective agrochemicals.
Used in Organic Compound Production:
(R)-2-Hydroxy-2-methyl-heptanitrile is utilized as a building block in the production of a range of organic compounds, capitalizing on its chemical reactivity to form new molecules with diverse applications across various industries.

Upstream product

• 110-43-0 n-pentyl methyl ketone 
• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 

Relevant academic research and scientific papers

Synthesis of aliphatic and α-halogenated ketone cyanohydrins with the hydroxynitrile lyase from Manihot esculenta

The potential of the hydroxynitrile lyase from Manihot esculenta towards ketone substrates was investigated. It was observed that the length of the aliphatic chain is a key parameter for the conversion of aliphatic, non-branched ketones. Smaller substrates are readily converted with high enantioselectivites, but the elongation of the chain length causes a significant loss in enzyme activity. For a number of halogenated, herein especially fluorinated, acetophenone derivatives the corresponding cyanohydrins have been synthesized with good to moderate enantioselectivities. Overcoming limitations: Ketone cyanohydrins are extremely useful intermediates for the synthesis of unusual tertiary alcohols. In this contribution, the limits of the hydroxynitrile lyase from Manihot esculenta towards such substrates are investigated and evaluated. High enantioselectivities are obtained in a simple two-phase system, even with very challenging fluorinated acetophenone derivatives.

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

Approach to (R)- and (S)-ketone cyanohydrins using almond and apple meal as the source of (R)-oxynitrilase

The synthesis of aliphatic and aromatic (R)-ketone cyanohydrins through the addition of hydrogen cyanide to the corresponding ketones and the synthesis of the (S)-enantiomers through the kinetic resolution of racemic ketone cyanohydrins has been studied in the presence of almond or apple meal. Substrate tolerance of the (R)-oxynitrilases towards ketones (R1R2C=O) is highly restricted compared to that of structurally similar aldehydes, reactivity following the order of H>Me>>Et for R2. In the case of aromatic methyl ketones reactivity difference (C6H5>>p-Me-C6H4 for R1) is notable.

Ueber die erste rekombinante Hydroxynitril-Lyase und ihre Anwendung in der Synthese von (S)-Cyanhydrinen

Keywords: Asymmetrische Synthesen; (S)-Cyanhydrine; Enzymkatalyse; Lyasen

(R)-Oxynitrilase Catalyzed Synthesis of (R)-Ketone Cyanohydrins

(R)-Oxynitrilase from almonds (Prunus amygdalus) catalyzed the enantioselective addition of HCN to ethyl alkyl ketones 1 in diisopropyl ether yielding (R)-ethyl alkyl ketone cyanohydrins (R)-2, which are hydrolyzed under acid catalysis to give the α-hydroxy acids (R)-3.This (R)-oxynitrilase also catalyzes the enantioselective addition in aqueous citrate buffer (50 mM, pH 4.0), as demonstrated for the preparation of (R)-methyl alkyl ketone cyanohydrins (R)-5 which are obtained in high enantiomeric excesses comparable to those in diisopropyl ether as solvent.

Synthese und Reaktionen optisch aktiver Cyanhydrine

Bei der grossen Bedeutung, die Cyanhydrine in der Technik und in der Organischen Chemie immer schon hatten, ist es erstaunlich, dass optisch aktive Cyanhydrine erst in den letzten Jahren intensiver untersucht und in der Synthese eingesetzt wurden.Der Grund dafuer ist wohl darin zu sehen, dass es erst in neurerer Zeit gelungen ist, chirale Cyanhydrine, hauptsaechlich mit enzymatischen Methoden, relativ einfach und in hoher optischer Reinheit herzustellen.Chirale Cyanhydrine sind, zumeist als Glycoside geschuetzt, in der Natur weit verbreitet.Annaehernd dreitausend Pflanzen und vielen Insekten dienen sie unter anderem als Abwehrstoffe gegen "Fresser".Ihre grosse Bedeutung in der Organischen Chemie beruht auf ihrem enormen Synthesepotential fuer die Gewinnung anderer wichtiger chiraler Verbindungen.In Wirkstoffen sind chirale Cyanhydrinbausteine nur vereinzelt enthalten.Wegen der Notwendigkeit, bei neuen Wirksubstanzen mit Chiralitaetszentren, saemtliche Stereoisomere herzustellen und sie bezueglich ihres Wirkungsspektrums sowie ihres Metabolismus zu untersuchen, ist die Entwicklung neuer und einfacher stereoselektiver Synthesen erforderlich.Chirale Cyanhydrine koennen hierbei wertwolle Ausgangsverbindungen sein.Im vorliegenden Artikel werden folgende Themen behandelt: die durch die Enzyme (R)- oder (S)-Oxynitrilase katalysierte enantioselektive Addition von Blausaeure an Aldehyde und Ketone zu (R)- bzw. (S)-Cyanhydrinen; die durch cyclische Dipeptide katalysierte enantioselektive Addition von Blausaeure an Aldehyde; die durch Lipasen und Esterasen katalysierte enantioselektive Hydrolyse bzw.Veresterung racemischer Cyanhydrine und Cyanhydrinester; Folgereaktionen der Nitrilgruppe chiraler Cyanhydrine zu optisch aktiven α-Hydroxycarbonsaeuren, α-Hydroxyaldehyden, α-Hydroxyketonen und 2-Aminoalkoholen; Folgereaktionen der OH-Gruppe chiraler Cyanhydrine durch Sulfonylaktivierung und anschliessende stereoselektive Substitution mit Nucleophilen unter Konfigurationsumkehr zu optisch aktiven α-Azidonitrilen, α-Aminonitrilen unf α-Fluornitrilen.

Enzyme-catalyzed synthesis of (R)-ketone-cyanohydrins and their hydrolysis to (R)-α-hydroxy-α-methyl-carboxylic acids

(R)-Ketone-cyanohydrins (R)-2 are obtained with high enantioselectivity from aliphatic ketones 1 and HCN in organic solvents using (R)-oxynitrilase ( EC 4.1.2.10) as catalyst. Acid catalyzed hydrolysis of the cyanohydrins (R)-2 affords the corresponding (R)-α-hydroxy-α-methyl-carboxylic acids (R)-3 without measurable racemization.