Quadrone, (+/-)-

Base Information

• Chemical Name: Quadrone, (+/-)-
• CAS No.: 74807-65-1
• Deprecated CAS: 87480-01-1
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• UNII: 498881H35R,T216NQ191Q
• Metabolomics Workbench ID: 144774
• Nikkaji Number: J20.422F
• Wikidata: Q76423441
• Mol file: 74807-65-1.mol

Synonyms:6,8b-Ethano-8bH-cyclopenta(de)-2-benzopyran-1,4-dione, octahydro-10,10-dimethyl-, (3aalpha,5abeta,6alpha,8aalpha,8balpha)-;quadrone

Chemical Property of Quadrone, (+/-)-

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 453

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CC23C4CCC1C2CC(=O)C3COC4=O)C
• Isomeric SMILES: CC1(C[C@@]23[C@H]4CC[C@@H]1[C@H]2CC(=O)[C@@H]3COC4=O)C

Technology Process of Quadrone, (+/-)-

There total 4 articles about Quadrone, (+/-)- 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:

(3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-66-9,117557-25-2,132831-49-3,132831-50-6) → (+/-)-quadrone (66550-08-1,74807-65-1,87480-01-1) + (3aR*,4S*,7S*,7aS*)-octahydro-8,8-dimethyl-3-methylene-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-67-0,83058-94-0,93219-11-5)

Guidance literature:

at 190 - 195 ℃;

DOI:10.1021/ja00404a026

Reference yield:

sodium acetate (127-09-3) → quadrone (66550-08-1,74807-65-1,87480-01-1) + terrecyclic acid (78739-67-0,83058-94-0,93219-11-5)

Guidance literature:

With cultura of Aspergillus terreus; for 172h;

DOI:10.1016/S0040-4039(01)91538-2

Reference yield:

(3aR*,4S*,7S*,7aS*)-octahydro-8,8-dimethyl-3-methylene-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-67-0,83058-94-0,93219-11-5) → (+/-)-quadrone (66550-08-1,74807-65-1,87480-01-1) + isoquadrone (74786-15-5,81130-69-0)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/ja00532a049

upstream raw materials:

sodium acetate

(3aR*,4S*,7S*,7aS*)-octahydro-8,8-dimethyl-3-methylene-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid

(3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid