287104-64-7

Basic information

• Product Name: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5S,6R)- (9CI)
• Synonyms: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5S,6R)- (9CI)
• CAS NO: 287104-64-7
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.16256
• Product Categories: ALCOHOL
• Mol File: 287104-64-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5S,6R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5S,6R)- (9CI)(287104-64-7)
• EPA Substance Registry System: 1,3-Cyclohexadiene-1-acetonitrile, 5,6-dihydroxy-, (5S,6R)- (9CI)(287104-64-7)

Safety Data

• Hazardous Substances Data: 287104-64-7(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 molecular weight is the mass of one mole of a substance, expressed in grams per mole (g/mol). It is calculated by adding the atomic weights of all the atoms in the molecule.

Explanation

The compound is derived from cyclohexadiene, which is a six-membered ring with two double bonds.

Explanation

The compound contains two hydroxyl (-OH) groups, which are functional groups consisting of an oxygen atom bonded to a hydrogen atom.

Explanation

The hydroxyl groups are located at the 5th and 6th positions of the cyclohexadiene ring.

Explanation

The stereochemistry of the compound is specified as (5S,6R), which indicates the configuration of the chiral centers (carbon atoms with four different substituents) in the molecule. "S" and "R" denote the absolute configuration of the chiral centers according to the Cahn-Ingold-Prelog priority rules.

Explanation

The compound may have potential applications in various fields, such as organic synthesis, pharmaceuticals, and other industries. However, its specific uses and properties may require further investigation and research.

Explanation

The specific uses and properties of the compound may not be fully understood and may require additional research to explore its potential applications and characteristics.

Molecular Weight

151.16 g/mol

Derivative of Cyclohexadiene

Yes

Hydroxyl Groups

Two

Hydroxyl Group Positions

5th and 6th

Stereochemistry

(5S,6R)

Potential Applications

Organic synthesis, pharmaceuticals, and other industries

Further Research Needed

Yes

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.