19036-56-7

Usage

Structure

Cycloheptane ring with a hydroxyl group at the 1-position and a carbonitrile group attached
The compound is composed of a seven-carbon ring structure with a hydroxyl (-OH) group attached to the first carbon and a cyano (-CN) group attached to the ring.

Usage

Building block in organic synthesis and pharmaceutical research
1-hydroxycycloheptanecarbonitrile is utilized as an intermediate compound in the production of various other chemical compounds, particularly in the fields of organic synthesis and pharmaceutical research.

Potential applications

Development of pharmaceuticals and agrochemicals
Due to its unique chemical properties, 1-hydroxycycloheptanecarbonitrile has potential applications in the creation of new pharmaceuticals and agrochemicals.

Upstream product

• 502-42-1 cycloheptanone 
• 151-50-8 potassium cyanide 
• 74-90-8 hydrogen cyanide 
• 64-17-5 ethanol 
• 143-33-9 sodium cyanide 

Downstream Products

• 74-90-8 hydrogen cyanide 
• 502-42-1 cycloheptanone 
• 98425-73-1 Cyclohepten-1-carbonsaeure-(1)-amid 
• 27873-57-0 6-Oxabicyclo<3.2.2>nonan-7-on 
• 91554-20-0 4-(cyclohept-1-enecarbonyl)-morpholine 
• 72233-47-7 1-Cycloheptene-1-carboxylic acid chloride 
• 111-14-8 oenanthic acid 
• 80904-20-7 4-cycloheptone-1-carbonitrile 
• 71-43-2 benzene 
• 20343-19-5 cyclohept-1-enecarbonitrile 
• 100-47-0 benzonitrile 
• 65-85-0 benzoic acid 
• 45732-95-4 1-(aminomethyl)cycloheptanol 

Relevant academic research and scientific papers

Synthesis, spectral, and structural characteristics of cyanohydrines derived from aliphatic cyclic ketones1

A series of cyanohydrines derived from cyclic aliphatic ketones was synthesized by acid-catalyzed nucleophilic addition reaction under the action of potassium cyanide. The products were characterized by means of multi-nuclear NMR spectroscopy (1H, 13C, 14N, 15N), mass spectrometry, elemental analysis, UV-Vis spectroscopy, refraction index measurements as well as vibrational spectroscopy. The structure of the cyanohydrine of cyclohexanone was elucidated by means of single crystal X-ray diffraction.

Synthesis of Disodium 3-cyclohepta-1,6-diene-1-carboxylate: A Seven-Membered Ring Analogue of Chorismate.

The synthesis of seven-membered ring analogue of chorismate, disodium 3--cyclohepta-1,6-diene-1-carboxylate (4c), was accomplished in 3percent overall yield from cycloheptanone.Compound χ was not processed by chorismate mutase, but it was a moderate inhibitor of the normal enzyme-catalyzed conversion of chorismate to prephenate.Prephenate analogue 5c did not inhibit the prephenate dehydrogenase catalyzed decarboxylation of prephenate.Thermolysis of the dimethyl ester 4c led to a complex mixture of products via 1,5-hydrogen migrations, Claisen rearrangement, and intramolecular Michael and Diels-Alder reactio n.The products were separated and identified on the basis of spectral and analytical data.

Synthesis of Succinonitrile Derivatives by Homocoupling from Cyanohydrin Derivatives with a Low-Valent Titanium Reagent

A method is described for synthesizing succinonitrile derivatives bearing alkyl or aryl substituents from cyanohydrin derivatives using low-valent titanium. The active species in this reaction is proposed to be a resonance hybrid of the TiIV nitrile enolate and TiIII alkyl radical.

Tandem alkylation-cyclization process via an O,C-dianion

A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the γ carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6.

Studies on phosphoroheterocycle chemistry III: An unusual way to 1,3,2-thiazaphospholidine-4-thione 2-sulfide derivatives

An unusual but efficient method for the synthesis of phosphoroheterocycles, 1,3,2-thiazaphospholidine-4-thione 2-sulfide derivatives, by the reaction of Lawesson's reagent with a variety of α-hydroxy nitriles has been developed. The possible mechanism of the reaction is proposed to involve thiation of hydroxy group in a first step, sequential addition of P-SH to the nitrile and rearrangement resulting in the title phosphoroheterocycles. The preliminary bioassays show that these heterocyclic compounds have herbicidal properties.

Lactone Formation in Superacidic Media

The reaction of substituted 1-hydroxycyclohexanecarboxylic acids in fluorosulphuric acid has been studied.Cyclisation takes place around 0 deg C, accompanied by rearrangement in appropriate cases, yielding the thermodynamically stable lactone or mixture of lactones.An unexpected feature of these reactions is that the carboxy-substituted cyclohexyl carbocation does not undergo ring contraction, unlike the unsubstituted cyclohexyl carbocation, although the cycloheptyl system contracts to cyclohexyl.We suggest that the cyclohexyl carbocation is strongly stabilised by carboxyl substitution, as a result of through-space interaction between the carboxyl oxygen atom and the carbocation centre.