5,6,7,7a,8,9,10,11-Octahydro-4H-benzo[ef]heptalene

Base Information

• Chemical Name: 5,6,7,7a,8,9,10,11-Octahydro-4H-benzo[ef]heptalene
• CAS No.: 65875-05-0
• Molecular Formula: C15H20
• Molecular Weight: 200.32
• DSSTox Substance ID: DTXSID50488910
• Wikidata: Q72497154
• Mol file: 65875-05-0.mol

Synonyms:5,6,7,7a,8,9,10,11-Octahydro-4H-benzo[ef]heptalene;65875-05-0;tricyclo[8.4.1.05,15]pentadeca-1(15),2,4-triene;DTXSID50488910;AKOS015901430;FT-0701624

Chemical Property of 5,6,7,7a,8,9,10,11-Octahydro-4H-benzo[ef]heptalene

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.545
• Boiling Point: 311.926°C at 760 mmHg
• Flash Point: 146.447°C
• PSA: 0.00000
• Density: 0.984
• LogP: 4.22300
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 200.156500638
• Heavy Atom Count: 15
• Complexity: 188

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2=C3C(C1)CCCCC3=CC=C2

Technology Process of 5,6,7,7a,8,9,10,11-Octahydro-4H-benzo[ef]heptalene

There total 8 articles about 5,6,7,7a,8,9,10,11-Octahydro-4H-benzo[ef]heptalene 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: 74.0%

5,6,7,7a,8,9,10,11-octahydro-4-benzo[ef]heptalenone → 5,6,7,7a,8,9,10,11-octahydro-4H-benzo[ef]heptalene (65875-05-0)

Guidance literature:

With triethylsilane; trifluoroacetic acid; at 60 ℃;

Reference yield:

1-Benzosuberone (826-73-3) → 5,6,7,7a,8,9,10,11-octahydro-4H-benzo[ef]heptalene (65875-05-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / benzene; mineral oil / 0.25 h / 0 °C

1.2: 20 °C / Reflux

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h

3.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 - 20 °C

4.1: sodium hydride / benzene; mineral oil / 0.17 h / 0 °C

4.2: 20 - 70 °C

5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h

6.1: sodium hydroxide / methanol; water / 3 h / 20 °C

7.1: polyphosphoric acid / 4 h / 110 °C

8.1: trifluoroacetic acid; triethylsilane / 60 °C

With triethylsilane; palladium 10% on activated carbon; hydrogen; sodium hydride; diisobutylaluminium hydride; trifluoroacetic acid; sodium hydroxide; In methanol; hexane; water; ethyl acetate; toluene; mineral oil; benzene;

DOI:10.1016/j.bmc.2013.04.053

Reference yield:

ethyl (6,7,8,9-tetrahydro-5-benzocycloheptenylidene)acetate (62677-72-9) → 5,6,7,7a,8,9,10,11-octahydro-4H-benzo[ef]heptalene (65875-05-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h

2.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 - 20 °C

3.1: sodium hydride / benzene; mineral oil / 0.17 h / 0 °C

3.2: 20 - 70 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h

5.1: sodium hydroxide / methanol; water / 3 h / 20 °C

6.1: polyphosphoric acid / 4 h / 110 °C

7.1: trifluoroacetic acid; triethylsilane / 60 °C

With triethylsilane; palladium 10% on activated carbon; hydrogen; sodium hydride; diisobutylaluminium hydride; trifluoroacetic acid; sodium hydroxide; In methanol; hexane; water; ethyl acetate; toluene; mineral oil; benzene;

DOI:10.1016/j.bmc.2013.04.053

upstream raw materials:

1-Benzosuberone

ethyl (6,7,8,9-tetrahydro-5-benzocycloheptenylidene)acetate

(6,7,8,9-tetrahydro-5H-5-benzocycloheptenyl)acetaldehyde

ethyl 4-(6,7,8,9-tetrahydro-5H-5-benzocycloheptenyl)-2-butenoate

Downstream raw materials:

methyl 4-[(5,6,7,7a,8,9,10,11-octahydro-4H-2-benzo[ef]heptalenyl)carbamoyl]benzoate

methyl 4-[(5,6,7,7a,8,9,10,11-octahydro-4H-2-benzo[ef]heptalenyl)carboxamido]benzoate

methyl 2-fluoro-4-[(5,6,7,7a,8,9,10,11-octahydro-4H-2-benzo[ef]heptalenyl)carboxamido]benzoate

methyl 2-chloro-4-[(5,6,7,7a,8,9, 10,11-octahydro-4H-2-benzo[ef]heptalenyl)carboxamido]benzoate