CID 13118284

Base Information

• Chemical Name: CID 13118284
• CAS No.: 81678-18-4
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• DSSTox Substance ID: DTXSID701316859
• Metabolomics Workbench ID: 47491
• Nikkaji Number: J988.011I
• Wikidata: Q104375853
• Mol file: 81678-18-4.mol

Synonyms:furanogermenone

Chemical Property of CID 13118284

Chemical Property:

• Vapor Pressure: 5.69E-05mmHg at 25°C
• Boiling Point: 346.6°C at 760 mmHg
• Flash Point: 162.5°C
• PSA: 30.21000
• Density: 0.992g/cm³
• LogP: 3.61830
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 232.146329876
• Heavy Atom Count: 17
• Complexity: 319

Purity/Quality:

98.5% ^*data from raw suppliers

FURANOGERMENONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC=C(CC2=C(CC1=O)C(=CO2)C)C
• Isomeric SMILES: C[C@H]1CC/C=C(/CC2=C(CC1=O)C(=CO2)C)\C

Technology Process of CID 13118284

There total 10 articles about CID 13118284 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: 76.0%

(E)-(S)-3,6,10-Trimethyl-4,5,6,7,8,11-hexahydro-cyclodeca[b]furan-5-ol (81678-31-1,81678-32-2) → 3,6,10-trimethyl-6,7,8,11-tetrahydro-4H-cyclodeca[b]furan-5-one (81678-18-4)

Guidance literature:

With pyridinium chlorochromate;

Reference yield:

(5R,6S)-3,6-dimethyl-6-vinyl-4,5,6,7-tetrahydrobenzofuran-5-ol (1416546-02-5) → 3,6,10-trimethyl-6,7,8,11-tetrahydro-4H-cyclodeca[b]furan-5-one (84939-51-5) + 3,6,10-trimethyl-6,7,8,11-tetrahydro-4H-cyclodeca[b]furan-5-one (81678-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether / Inert atmosphere

2.2: 0.25 h / -78 °C / Inert atmosphere

3.1: toluene / 7 h / 120 °C / Inert atmosphere

With tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; In diethyl ether; dichloromethane; toluene; 3.1: |Oxy-Cope Rearrangement;

DOI:10.1021/ol3031999

Reference yield:

(S)-3,6-dimethyl-6-vinyl-6,7-dihydrobenzofuran-5(4H)-one (1416546-04-7) → 3,6,10-trimethyl-6,7,8,11-tetrahydro-4H-cyclodeca[b]furan-5-one (84939-51-5) + 3,6,10-trimethyl-6,7,8,11-tetrahydro-4H-cyclodeca[b]furan-5-one (81678-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / diethyl ether / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

2.1: toluene / 7 h / 120 °C / Inert atmosphere

With tert.-butyl lithium; In diethyl ether; toluene; 2.1: |Oxy-Cope Rearrangement;

DOI:10.1021/ol3031999

upstream raw materials:

(E)-(S)-3,6,10-Trimethyl-4,5,6,7,8,11-hexahydro-cyclodeca[b]furan-5-ol

(5R,6S)-3,6-dimethyl-6-vinyl-4,5,6,7-tetrahydrobenzofuran-5-ol

(S)-3,6-dimethyl-6-vinyl-6,7-dihydrobenzofuran-5(4H)-one

(5R,6S)-3,6-dimethyl-5-(prop-1-en-2-yl)-6-vinyl-4,5,6,7-tetrahydrobenzofuran-5-ol

Downstream raw materials:

(2S)-5-(benzyloxy)-2-methylpentan-1-ol

Benzoic acid (S)-5-methanesulfonyloxy-6-[2-(2-methanesulfonyloxy-propyl)-4-methyl-furan-3-yl]-4-methyl-hexyl ester

Benzoic acid (S)-5-hydroxy-6-[2-(2-hydroxy-propyl)-4-methyl-furan-3-yl]-4-methyl-hexyl ester

3-((E)-(S)-6-Benzyloxy-3-methyl-hex-1-enyl)-4-methyl-2-((Z)-propenyl)-furan