1,3,4,5,6,6-Hexamethylbicyclo[3.1.0]hex-3-en-2-one

Base Information

• Chemical Name: 1,3,4,5,6,6-Hexamethylbicyclo[3.1.0]hex-3-en-2-one
• CAS No.: 2206-69-1
• Molecular Formula: C12H18 O
• Molecular Weight: 178.274
• Hs Code.: 2914299000
• DSSTox Substance ID: DTXSID50944687
• Mol file: 2206-69-1.mol

Synonyms:2206-69-1;1,3,4,5,5,6-Hexamethylbicyclo[3.1.0]hex-3-en-2-one;1,3,4,5,6,6-hexamethylbicyclo[3.1.0]hex-3-en-2-one;1,3,4,5,5,6-Hexamethylbicyclo(3.1.0)hex-3-en-2-one;DTXSID50944687

Chemical Property of 1,3,4,5,6,6-Hexamethylbicyclo[3.1.0]hex-3-en-2-one

Chemical Property:

• Vapor Pressure: 0.11mmHg at 25°C
• Boiling Point: 221°C at 760 mmHg
• Flash Point: 94.2°C
• PSA: 17.07000
• Density: 0.984g/cm³
• LogP: 2.95790
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 178.135765193
• Heavy Atom Count: 13
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2(C(C2(C1=O)C)(C)C)C)C

Technology Process of 1,3,4,5,6,6-Hexamethylbicyclo[3.1.0]hex-3-en-2-one

There total 2 articles about 1,3,4,5,6,6-Hexamethylbicyclo[3.1.0]hex-3-en-2-one 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: 72.0%

2,3,4,5,6,6-hexamethylcyclohexa-2,4-dien-1-one (3854-96-4) → 1,3,4,5,6,6-hexamethylbicyclo<3.1.0>hex-3-en-2-one (2206-69-1)

Guidance literature:

With boron trifluoride diethyl etherate; tribromo{(S)-1,3,3-tris(3',5'-dimethyl-[1,1'-biphenyl]-2-yl)tetrahydro-1H,3H-7l4-pyrrolo[1,2-c][1,3,2]oxazaborol-7-yl}aluminate; In dichloromethane; at -78 ℃; for 5h; Reagent/catalyst; enantioselective reaction; Irradiation; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.9b12068

Reference yield:

→ 1,3,4,5,6,6-hexamethylbicyclo<3.1.0>hex-3-en-2-one (2206-69-1)

Guidance literature:

/Z0930412091/, K2CO3, W.;

DOI:10.1039/c29700001581

Reference yield:

1,3,4,5,6,6-hexamethylbicyclo<3.1.0>hex-3-en-2-one (2206-69-1) → Hexamethylbenzene (87-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.81 g / diethyl ether / 6 h / 25 °C

2: 9 percent Chromat_. / H₂SO₄ / H₂O / 0.5 h / Ambient temperature; Irradiation

With sulfuric acid; In diethyl ether; water;

upstream raw materials:

2,3,4,5,6,6-hexamethylcyclohexa-2,4-dien-1-one

Downstream raw materials:

1,1,3,4,5,6-hexamethyl-2-hydroxybenzenonium ion

1,2,3,4,5-pentamethylcyclopentadiene

Hexamethylbenzene

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene