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
• Article Data: 20

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

Description

(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol is a unique diol compound characterized by its specific stereochemistry and functional groups. It features a methyl group and a conjugated diene system within a cyclohexane ring, which endows it with distinct reactivity and potential applications.

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

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

Downstream Products

• 403986-34-5 (1S,2R,3R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-methylcyclohex-4-ene-1,2,3-triol 
• 403986-36-7 (1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol 
• 1544400-68-1 (1S,2R,5R)-3-methylcyclohex-3-ene-1,2,5-triol 
• 1544400-66-9 (1R,4R,5R)-4,5-dihidroxy-5-methylcyclohex-5-ene-1-ylacetate 
• 15806-70-9 (+/-)-1ξ-methyl-cyclohexanediol-(2r.3c) 
• 1544400-76-1 (1S,2R,3R,5S)-3-methylcyclohexan-1,2,5-triol 
• 108-39-4 3-methyl-phenol 

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

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.

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