41977-20-2

Basic information

• Product Name: (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol
• Synonyms: (1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol; 3,5-cyclohexadiene-1,2-diol, 3-methyl-, (1S,2R)-
• CAS NO: 41977-20-2
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.1531
• Mol File: 41977-20-2.mol

Chemical Properties

• Boiling Point: 234.3°C at 760 mmHg
• Flash Point: 111.4°C
• Density: 1.201g/cm³
• Vapor Pressure: 0.00978mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol(41977-20-2)
• EPA Substance Registry System: (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol(41977-20-2)

Safety Data

• Hazardous Substances Data: 41977-20-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol is used as a building block in organic synthesis for the production of pharmaceuticals, agrochemicals, and fine chemicals. Its unique structure and properties make it a valuable component in the synthesis of various complex organic molecules.
Used in Research:
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol is used as a target compound in research for asymmetric synthesis and catalysis. Its stereochemistry and functional groups provide opportunities for the development of novel synthetic methods and the exploration of new catalytic processes.

Upstream product

• 154097-65-1 (1S,2S,3R,4R)-5-methyl-5-cyclohexene-1,2,3,4-tetraol 
• 40635-67-4 acetoxyisobutyryl bromide 
• 108-88-3 toluene 
• 173381-12-9 (1S,2S)-1,2-di-tert-butyldimethylsiloxy-3-bromocyclohexa-3,5-diene 

Downstream Products

• 131043-52-2 (1R,7S,10R,11S)-10,11-Dihydroxy-1-methyl-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 
• 125164-90-1 (1S,2S,3S,4R)-1-Methyl-cyclohex-5-ene-1,2,3,4-tetraol 
• 141478-45-7 (-)-(1S,2R)-3-methyl-3-cyclohexene-1,2-diol 
• 114818-66-5 (2R,3S)-1-methyl-2,3-diacetoxycyclohexa-4,6-diene 
• 41977-23-5 1(S)-(benzoyloxy)-2(R)-hydroxy-3(S)-methylcyclohexane 
• 41977-23-5 1(S)-(benzoyloxy)-2(R)-hydroxy-3(R)-methylcyclohexane 
• 578-58-5 2-methylmethoxybenzene 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 775343-12-9 (3aS,4R,5S,6R,7S,7aS)-5,6-dihydroxy-7-methyl-3a,4,7,7a-tetrahydroethanoisobenzofuran-(3H)-one 
• 488-17-5 3-methylbenzene-1,2-diol 
• 900791-55-1 C₂₄H₂₄O₆ 
• 900791-57-3 C₂₄H₂₄O₆ 
• 900791-68-6 (+)-(1S,2S,3S,4S)-2-methyl-5-cyclohexene-1,2,3,4-tetraol 
• 900791-85-7 (1R,2R,5R,6R)-6-(acetyloxy)-2,5-dibromo-1-methyl-3-cyclohexenyl acetate 

Relevant articles and documents

Diels–Alder reaction of two green chiral precursors. Approach to natural product like structures

Diels–Alder cycloaddition between an enantiomerically pure protected cis-cyclohexadiene diol metabolite and optically pure levoglucosenone derived from cellulose gave rise to complex pentacyclic natural product like structures in a chemically succinct pro

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used in the synthesis of ampelomins and deoxy-carbasugars

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used as important intermediates for the preparation of ampelomins and deoxy-carbasugars was studied. These olefins were obtained in few steps from a chiral cis-diol resulting from microbial oxidation of toluene. Although the stereoselective hydrogenation of this type of substrates is difficult, high yields were obtained for heterogeneous hydrogenation using Adam's catalyst, where steric hindrance controlled the stereochemical outcome of the process. On the other hand, for homogeneous hydrogenation of similar olefins using Crabtree's catalyst, coordination with the allylic alcohols allowed for a controlled hydrogen addition from the more hindered face. In this manner two protocols for the hydrogenation of these types of substrates resulting in complementary stereoselectivities are described.

Aza and oxo Diels-Alder reactions using cis-cyclohexadienediols of microbial origin: Chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds

Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene.

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used in the synthesis of ampelomins and deoxy-carbasugars

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used as important intermediates for the preparation of ampelomins and deoxy-carbasugars was studied. These olefins were obtained in few steps from a chiral cis-diol resulting from microbial o

Concise chemoenzymatic synthesis of gabosine A, ent-epoformin and ent-epiepoformin

An efficient methodology has been developed to synthesize three related enantiomerically pure natural and unnatural compounds, based on a chemoenzymatic approach. We confirmed the usefulness of 3-methyl-cis-1,2-cyclohexadienediol derived from a biotransfo

syn-benzene dioxides: Chemoenzymatic synthesis from 2,3-cis-dihydrodiol derivatives of monosubstituted benzenes and their application in the synthesis of regioisomeric 1,2- and 3,4-cis-dihydrodiols and 1,4-dioxocins

cis-2,3-Dihydrodiol metabolites of monosubstituted halobenzenes and toluene have been used as synthetic precursors of the corresponding 3,4-cis-dihydrodiols. Enantiopure syn-benzene dioxide intermediates were reduced to the 3,4-cis-dihydrodiols and therma

Chemoenzymatic synthesis of the trans-dihydrodiol isomers of monosubstituted benzenes via anti-benzene dioxides

Enantiopure cis-2,3-dihydrodiols, available from dioxygenase-catalysed cis-dihydroxylation of monosubstituted benzene substrates, have been used as synthetic precursors of the corresponding trans-3,4-dihydrodiols. The six-step chemoenzymatic route from ci

Medium-scale preparation of useful metabolites of aromatic compounds via whole-cell fermentation with recombinant organisms

The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10-15L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.

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.

An unusual samarium diiodide mediated reductive ring contraction of a tricyclic oxazine to a highly-functionalized cyclopentane and cyclobutane.

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