Isoquadrone

Base Information

• Chemical Name: Isoquadrone
• CAS No.: 81130-69-0
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• DSSTox Substance ID: DTXSID901001802
• Wikidata: Q82995810
• Mol file: 81130-69-0.mol

Synonyms:Isoquadrone;BRN 5280366;2H-5,7b-Ethanoindeno(1,7-bc)furan-2,7(7ah)-dione, hexahydro-7a,9,9-trimethyl-, (2aR-(2a-alpha,5-alpha,5a-beta,7a-alpha,7b-alpha)-;81130-69-0;DTXSID901001802;LS-66364;7a,9,9-Trimethylhexahydro-2H-5,7b-ethanoindeno[1,7-bc]furan-2,7(7aH)-dione

Chemical Property of Isoquadrone

Chemical Property:

• Vapor Pressure: 1.31E-06mmHg at 25°C
• Boiling Point: 400.1°Cat760mmHg
• Flash Point: 178.5°C
• Density: 1.21g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC23C4CCC1C2CC(=O)C3(OC4=O)C)C

Technology Process of Isoquadrone

There total 10 articles about Isoquadrone 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:

(1R*,6S*,7S*)-10,10-dimethyl-4-oxotricyclo<4.3.2.02,6>undec-2-en-7-carboxylic acid (78739-64-7,82978-37-8,102849-98-9,117557-24-1,132831-32-4) → isoquadrone (74786-15-5,81130-69-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium diisopropylamide / 1.) THF, -23 deg C, 1.25 h, 2.) 5 min

2: hydrogen / 5percent Pd-C / methanol / 1 h / Ambient temperature

3: 4.8 mg / tosyl acid hydrate / benzene / 1 h / Heating

With hydrogen; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In methanol; benzene;

DOI:10.1021/ja00404a026

Reference yield:

(3aR*,4S*,7S*,7aS*)-octahydro-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-63-6,90820-84-1,117557-23-0) → isoquadrone (74786-15-5,81130-69-0)

Guidance literature:

Multi-step reaction with 5 steps

1: ethyl acetate / 3 h / Ambient temperature

2: 1.00 g / 30percent H₂O₂, pyridine / CH₂Cl₂ / 0.75 h / Ambient temperature

3: 1.) lithium diisopropylamide / 1.) THF, -23 deg C, 1.25 h, 2.) 5 min

4: hydrogen / 5percent Pd-C / methanol / 1 h / Ambient temperature

5: 4.8 mg / tosyl acid hydrate / benzene / 1 h / Heating

With pyridine; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/ja00404a026

Reference yield:

methyl (1R*,2S*,6S*,7S*)-10,10-dimethyl-4-oxotricyclo<4.3.2.02,6>undec-2-en-7-carboxylate (78739-62-5) → isoquadrone (74786-15-5,81130-69-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / aq. KOH / methanol / 1.5 h / Heating

2: ethyl acetate / 3 h / Ambient temperature

3: 1.00 g / 30percent H₂O₂, pyridine / CH₂Cl₂ / 0.75 h / Ambient temperature

4: 1.) lithium diisopropylamide / 1.) THF, -23 deg C, 1.25 h, 2.) 5 min

5: hydrogen / 5percent Pd-C / methanol / 1 h / Ambient temperature

6: 4.8 mg / tosyl acid hydrate / benzene / 1 h / Heating

With pyridine; potassium hydroxide; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/ja00404a026

upstream raw materials:

(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

(1R^*,6S^*,7S^*)-10,10-dimethyl-4-oxotricyclo<4.3.2.0^2,6>undec-2-en-7-carboxylic acid

(1R,3aS,4S,7S,7aS)-8,8-Dimethyl-2-oxo-1-phenylselanyl-octahydro-3a,7-ethano-indene-4-carboxylic acid

Refernces

• 1、 Danishefsky, Samuel,Vaughan, Kenward,Gadwood, Robert C.,Tsuzuki, Kazuo. "Total Synthesis of dl-Quadrone". . p. 4262 - 4263. Retrieved 2007/10/02.