(1S,6R)-1,6-dihydroxycyclohexa-2,4-dienecarboxylic acid

Base Information

• Chemical Name: (1S,6R)-1,6-dihydroxycyclohexa-2,4-dienecarboxylic acid
• CAS No.: 32359-20-9
• Molecular Formula: C7H8 O4
• Molecular Weight: 156.138
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID60186076
• Nikkaji Number: J1.686.130H
• Wikidata: Q27117306
• Metabolomics Workbench ID: 55717
• Mol file: 32359-20-9.mol

Synonyms:cyclohexadiene-1,2-diol-1-carboxylic acid

Chemical Property of (1S,6R)-1,6-dihydroxycyclohexa-2,4-dienecarboxylic acid

Chemical Property:

• Vapor Pressure: 2.18E-07mmHg at 25°C
• Boiling Point: 381.5°Cat760mmHg
• Flash Point: 198.7°C
• PSA: 77.76000
• Density: 1.598g/cm³
• LogP: -0.71100
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 156.04225873
• Heavy Atom Count: 11
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(C(C=C1)(C(=O)O)O)O
• Isomeric SMILES: C1=C[C@H]([C@@](C=C1)(C(=O)O)O)O

Technology Process of (1S,6R)-1,6-dihydroxycyclohexa-2,4-dienecarboxylic acid

There total 3 articles about (1S,6R)-1,6-dihydroxycyclohexa-2,4-dienecarboxylic acid 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: 92.0%

sodium benzoate (532-32-1) → (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9)

Guidance literature:

With D-Fructose; benzoate dioxygenase from Ralstonia eutropha B₉; sodium succinate; at 30 ℃; for 102h; Enzymatic reaction;

DOI:10.1021/acs.orglett.0c00708

Reference yield:

benzoic acid (65-85-0,8013-63-6) → (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9)

Guidance literature:

With Ralstonia eutropha B₉; optical yield given as %ee; Enzymatic reaction;

DOI:10.1055/s-0030-1259694

Reference yield:

sodium benzoate (532-32-1) → (1R,2S)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid + (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9)

Guidance literature:

With Alcaligenes eutrophus B₉; In various solvent(s); at 30 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ol010151m

upstream raw materials:

sodium benzoate

benzoic acid

Downstream raw materials:

(-)-(1S,6R)-methyl 1,6-dihydroxycyclohexa-2,4-dienecarboxylate

(-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate

methyl (1S,6R)-1-hydroxy-6-((trimethylsilyl)oxy)cyclohexa-2,4-diene-1-carboxylate

doxycycline hydrochloride

Refernces

• 1、 Collins, Jonathan A.,Duncan, Madeleine M.,Gerry, Christopher J.. "A Chemoenzymatic Formal Synthesis of Epoxyquinols A and B". supporting information. p. 2193 - 2197. Retrieved 2019/11/25.
• 2、 Adams, David R.,Van Kempen, Johannes,Hudlicky, Jason R.,Hudlicky, Tomas. "Chemoenzymatic approach to synthesis of hydroxylated pyrrolidines from benzoic acid". . p. 1255 - 1274. Retrieved 2016/10/30.