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

General Description

(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol is a chemical compound with a unique structure and properties. It belongs to the class of diols, which are organic compounds containing two hydroxyl groups. The (1S,2R) in the name indicates the stereochemistry of the molecule, specifying the configuration of the chiral centers. The presence of a methyl group and a conjugated diene system in the cyclohexane ring confers distinct reactivity and potential applications for this compound. It can be used as a building block in organic synthesis, for example in the production of pharmaceuticals, agrochemicals, and fine chemicals. Additionally, its stereochemistry and functional groups make it an interesting target for research in asymmetric synthesis and catalysis. Overall, (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol is a versatile and valuable compound with various potential uses in the field of chemistry.

Upstream product

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

Downstream Products

• 95-48-7 ortho-cresol 
• 210633-64-0 (2S,3aR,7aS)-3a,7a-dihydro-2-(4-methoxyphenyl)-4-methyl-1,3-benzodioxole 
• 278600-83-2 phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.0^2,6]undec-10-en-9-yl]methanone 
• 41977-23-5 1(S)-(benzoyloxy)-2(R)-hydroxy-3(S)-methylcyclohexane 
• 41977-23-5 1(S)-(benzoyloxy)-2(R)-hydroxy-3(R)-methylcyclohexane 
• 114818-66-5 (2R,3S)-1-methyl-2,3-diacetoxycyclohexa-4,6-diene 
• 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 

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.

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