(1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol

Base Information

• Chemical Name: (1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol
• CAS No.: 41977-20-2
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• DSSTox Substance ID: DTXSID50962124
• Nikkaji Number: J463.417I
• Wikidata: Q27098106
• Metabolomics Workbench ID: 50158
• Mol file: 41977-20-2.mol

Synonyms:(1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol;toluene-cis-dihydrodiol;toluene-cis-1,2-dihydrodiol;41977-20-2;Cis-3-methylcyclohexa-3,5-diene-1,2-diol;toluene cis-glycol;3-methylcyclohexa-3,5-diene-1,2-diol;toluene-cis-1,2-dihydroxydiol;SCHEMBL2632526;CHEBI:15565;DTXSID50962124;AKOS006272137;C04592;(+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene;Q27098106;(+)-cis-1S,2R-dihydroxy-3-methyl-cyclohexa-3,5-diene

Chemical Property of (1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol

Chemical Property:

• Vapor Pressure: 0.00978mmHg at 25°C
• Boiling Point: 234.3°Cat760mmHg
• Flash Point: 111.4°C
• Density: 1.201g/cm³
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC(C1O)O
• Isomeric SMILES: CC1=CC=C[C@@H]([C@@H]1O)O

Technology Process of (1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol

There total 9 articles about (1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

toluene (108-88-3,15644-74-3,16713-13-6) → (2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene (41977-20-2)

Guidance literature:

With Pseudomonas putida UV₄; oxygen; Enzymatic reaction;

DOI:10.1039/b000753f

Reference yield: 53.0%

(1S,2S,3R,4R)-5-methyl-5-cyclohexene-1,2,3,4-tetraol (154097-65-1) + acetoxyisobutyryl bromide (40635-67-4) → (2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene (41977-20-2) + (1S,2R)-4-methyl-3,5-cyclohexadiene-1,2-diol

Guidance literature:

(1S,2S,3R,4R)-5-methyl-5-cyclohexene-1,2,3,4-tetraol; acetoxyisobutyryl bromide; In acetonitrile; at 0 - 20 ℃;

With sodium methylate; In diethyl ether; at 0 - 20 ℃;

With potassium carbonate; palladium diacetate; In tetrahydrofuran; water; for 12h; Further stages.;

DOI:10.1039/b704584k

Reference yield: 30.0%

(1S,2S)-3-Iodo-6-methyl-cyclohexa-3,5-diene-1,2-diol → (2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene (41977-20-2) + cis-1,2-dihydrocatechol (154333-41-2)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1039/c39950000117

upstream raw materials:

toluene

(1S,2S,3R,4R)-5-methyl-5-cyclohexene-1,2,3,4-tetraol

acetoxyisobutyryl bromide

(1S,2S)-1,2-di-tert-butyldimethylsiloxy-3-bromocyclohexa-3,5-diene

Downstream raw materials:

(1S,2S,3S,4R)-1-Methyl-cyclohex-5-ene-1,2,3,4-tetraol

(-)-(1S,2R)-3-methyl-3-cyclohexene-1,2-diol

1(S),2(R)-dihydroxy-3(S)-methylcyclohexane

1(S),2(R)-dihydroxy-3(R)-methylcyclohexane

Refernces

• 1、 Pazos, Mariana,Martínez, Sebastián,Vila, María Agustina,Rodríguez, Paola,Veiga, Nicolás,Seoane, Gustavo,Carrera, Ignacio. "Aza and oxo Diels-Alder reactions using cis-cyclohexadienediols of microbial origin: Chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds". . p. 1436 - 1447. Retrieved 2015/12/09.
• 2、 Lagreca, María Eugenia,Carrera, Ignacio,Seoane, Gustavo A.,Brovetto, Margarita. "Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used in the synthesis of ampelomins and deoxy-carbasugars". . p. 853 - 856. Retrieved 2014/02/14.