Quadrone

Base Information

• Chemical Name: Quadrone
• CAS No.: 66550-08-1
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• NSC Number: 284437
• Wikidata: Q104922770
• ChEMBL ID: CHEMBL2000102
• Mol file: 66550-08-1.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:

• Vapor Pressure: 3.18E-07mmHg at 25°C
• Melting Point: 183-184 °C
• Boiling Point: 418.8°Cat760mmHg
• Flash Point: 187.6°C
• PSA: 43.37000
• Density: 1.21g/cm³
• LogP: 2.19090
• 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:

>98% by HPLC ^*data from raw suppliers

Quadrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC23C4CCC1C2CC(=O)C3COC4=O)C
• Uses: Quadrone is an unusual sesquiterpene metabolite isolated from Aspergillus terreus and first reported in 1978. Quadrone exhibits antitumor activity but has not been extensively investigated. Quadrone is a sesquiterpene metabolite which exhibits antitumor activity.

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