4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-one

Base Information

• Chemical Name: 4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-one
• CAS No.: 79-76-5
• Molecular Formula: C13H20 O
• Molecular Weight: 192.301
• DSSTox Substance ID: DTXSID5052543
• Wikidata: Q105251709
• Mol file: 79-76-5.mol

Synonyms:DTXSID5052543

Chemical Property of 4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-one

Chemical Property:

• Vapor Pressure: 0.00798mmHg at 25°C
• Boiling Point: 267.8 °C at 760 mmHg
• Flash Point: 112.3 °C
• PSA: 17.07000
• Density: 0.91 g/cm³
• LogP: 3.51410
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 271

Purity/Quality:

97% ^*data from raw suppliers

4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C=CC1C(=C)CCCC1(C)C
• Description: Synthesis: By condensation of cyclogeranic aldehyde with acetone, followed by separation from the (3-ionone-rich reaction mixture.
• Uses: 4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one is an aroma compound found as an analyte in food products such as raspberry juice, Sophora japonica oil and in Osmanthus flowers. 4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one is also used as a flavouring substance.

Technology Process of 4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-one

There total 7 articles about 4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-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: 67.0%

(2,2-dimethyl-6-methylenecyclohexyl)methanol (472-19-5,4352-33-4) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → γ-ionone (79-76-5)

Guidance literature:

(2,2-dimethyl-6-methylenecyclohexyl)methanol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 3h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

1-triphenylphosphoranylidene-2-propanone; In toluene; for 16h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201503403

Reference yield:

(E)-4-(2,2-Dimethyl-6-methylene-cyclohexyl)-but-3-en-2-ol (472-76-4) → γ-ionone (79-76-5)

Guidance literature:

With manganese(IV) oxide; In chloroform; for 6h; Heating;

DOI:10.1016/j.tetasy.2005.02.021

Reference yield:

Acetic acid (E)-3-(2,2-dimethyl-6-methylene-cyclohexyl)-1-methyl-allyl ester → γ-ionone (79-76-5)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH / methanol / 20 °C

2: MnO₂ / CHCl₃ / 6 h / Heating

With manganese(IV) oxide; potassium hydroxide; In methanol; chloroform;

DOI:10.1016/j.tetasy.2005.02.021

upstream raw materials:

(E)-4-(2,2-Dimethyl-6-methylene-cyclohexyl)-but-3-en-2-ol

alpha-ionol

(2E)-1-methyl-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenyl acetate

methyl (+/-)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate

Downstream raw materials:

3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal

Ethinyl-dihydro-γ-jonol

4-(2',2'-Dimethyl-6'-methylidenecyclohexyl)butan-2-one