365458-96-4

Basic information

• Product Name: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5R,6S)-rel- (9CI)
• Synonyms: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5R,6S)-rel- (9CI)
• CAS NO: 365458-96-4
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.16256
• Product Categories: ALCOHOL
• Mol File: 365458-96-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5R,6S)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5R,6S)-rel- (9CI)(365458-96-4)
• EPA Substance Registry System: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5R,6S)-rel- (9CI)(365458-96-4)

Safety Data

• Hazardous Substances Data: 365458-96-4(Hazardous Substances Data)

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule. In this case, the compound has 8 carbon (C), 9 hydrogen (H), 1 nitrogen (N), and 2 oxygen (O) atoms.

Explanation

The compound is derived from cyclohexadiene, which is a six-membered ring with two double bonds. It has an acetonitrile group (a carbon-nitrogen triple bond and a cyano group) and two hydroxyl groups (OH) attached to the ring.

Explanation

The stereochemistry of the compound is described by the (5R,6S)-relconfiguration, which indicates the spatial arrangement of the atoms at the 5th and 6th positions of the cyclohexadiene ring. The "R" and "S" notations are based on the Cahn-Ingold-Prelog priority rules and describe the three-dimensional arrangement of the substituents around the chiral centers.

Explanation

The compound may have potential applications in the pharmaceutical industry, possibly as a precursor to other compounds or as a building block for more complex molecules. It could also be used in organic synthesis for the creation of various organic compounds.

Explanation

While the compound has potential applications, further research and testing are required to fully understand its properties, reactivity, and potential uses in various industries. This may include studying its stability, solubility, and potential interactions with other compounds.

Structure

Cyclohexadiene derivative with an acetonitrile group and two hydroxyl groups

Stereochemistry

(5R,6S)-relconfiguration

Potential Applications

Pharmaceutical industry or organic synthesis

Further Research

Necessary to determine specific uses and properties

Upstream product

• 140-29-4 phenylacetonitrile 

Relevant articles and documents

Recombinant chlorobenzene dioxygenase from Pseudomonas sp. P51: A biocatalyst for regioselective oxidation of aromatic nitriles

An efficient biocatalyst was developed for the cis-dihydroxylation of aromatic nitriles. The chlorobenzene dioxygenase (CDO) genes of Pseudomonas sp. strain P51 were cloned under the strict control of the Palk promoter of Pseudomonas putida GPo1. Escherichia coli JM101 cells carrying the resulting plasmid pTEZ30 were used for the biotransformation of benzonitrile in a 2-L stirred tank bioreactor. Use of a stable expression system resulted in an average specific activity and an average volumetric productivity of 1.47 U/g cdw and 120 mg of product/h/L, respectively. The values represent a three-fold increase compared to the results of the similar biotransformations with E. coli JM101 (pTCB144) where the genes of CDO were expressed under the control of lac promoter. The productivity of the cis-dihydroxylation process was limited by product toxicity. Removal of the products at toxic concentrations by means of an external charcoal column resulted in an additional increase in product concentration by 43%. E. coli JM101 (pTEZ30) was further used for the regio- and stereospecific dihydroxylations of various monosubstituted benzonitriles, benzyl cyanide, and cinnamonitrile. Biotransformations resulted in products with 42.9-97.1% enantiomeric excess. Initial enzymatic activities and isolated yields were obtained in the range of 1.7-4.7 U/g cdw and of 3-62%, respectively.

Enantioselective toluene dioxygenase catalysed di- and tri-hydroxylation of monosubstituted benzenes

Asymmetric cis-dihydroxylation to yield diols 2A-2G and sequential benzylic monohydroxylation-cis-dihydroxylation to yield triols 4A-4G (trihydroxylation), occurred during biotransformation of a series of monosubstituted alkylbenzene substrates 1A-1G using toluene dioxygenase, a biocatalyst present in Pseudomonas putida UV4. Dioxygenase-catalysed cis-dihydroxylation of the R and S benzylic alcohol enantiomers 3B-3D, 3B′-3D′ gave the corresponding enantiopure triols 4B-4D, 4B′-4D′. Biotransformation of substrates 1J-1L yielded cis-diols 2J-2L and a minor triol metabolite 4A. Benzylic alcohols 3J-3L were postulated as unstable intermediates yielding triol 4A via benzaldehyde 5 and benzyl alcohol 3A intermediates, cis-Dihydroxylation of monosubstituted benzylic substrates containing bulky groups (1H, 1I) or 1,4-dialkyl-substituted benzene substrates (10A-10C) gave the corresponding cis-dihydrodiol metabolites (2H, 2I, 11A-11C) exclusively. The cis-diols 2A-2L, 11A-11C and triols 4A-4F, 4B′-4D′ were stereochemically assigned as single enantiomers of 1S,2R-configuration based on NMR and CD spectroscopy. The absolute configurations of the exocylic chiral centres in the triol bioproducts 4A-4F, 4B′-4D′ were established by stereochemical correlation and aromatisation/hydrogenation to yield the corresponding enantiopure phenolic benzylic alcohols having similar CD spectra.