4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone

Base Information

• Chemical Name: 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone
• CAS No.: 20483-36-7
• Molecular Formula: C13H20 O
• Molecular Weight: 192.301
• Hs Code.: 2914299000
• European Community (EC) Number: 243-847-3
• UNII: XZS4VD987O
• DSSTox Substance ID: DTXSID0066618
• Nikkaji Number: J280.604E
• Wikidata: Q27160440
• RXCUI: 2557365
• Metabolomics Workbench ID: 47630
• Mol file: 20483-36-7.mol

Synonyms:Dehydrodihydroionone;20483-36-7;4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone;Dihydrodehydro-beta-ionone;FEMA No. 3447;4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)butan-2-one;4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one;2-Butanone, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-;UNII-XZS4VD987O;XZS4VD987O;EINECS 243-847-3;Dihydrodehydro-.beta.-ionone;4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)butan-2-one;FEMA 3447;7,8-Dihydro-3,4-dehydro-.beta.-ionone;4-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-butanone;4-(2,6,6-trimethyl cyclohexa-1,3-dienyl) butane-2-one;DTXSID0066618;SCHEMBL10460910;CHEBI:88549;DEHYDRODIHYDROIONONE [FHFI];7,8-Dihydro-3,4-dehydro-b-ionone;7,8-dihydro-3,4-dehydro-beta-ionone;3,4-didehydro-7,8-dihydro-beta-ionone;A937334;Q27160440;4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanon;4-(2,6,6-trimethyl-1-cyclohexa-1,3-dienyl)butan-2-one;4 - (2,6,6 - trimethyl - 1,3 - cyclohexadien - 1 - yl) butan - 2 - one

Chemical Property of 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone

Chemical Property:

• Vapor Pressure: 0.00816mmHg at 25°C
• Boiling Point: 267.4°Cat760mmHg
• Flash Point: 95.6°C
• PSA: 17.07000
• Density: 0.893g/cm³
• LogP: 3.65820
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC=C1)(C)C)CCC(=O)C
• Uses: Dihydrodehydro-β-ionone was identified as a volatile oil from the leaves and stems of Albizia julibrissin Durazz.

Technology Process of 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone

There total 7 articles about 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 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%

(3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one (14398-35-7) → 4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one (20483-36-7)

Guidance literature:

With triphenylstannane; In benzene; for 144h; Heating;

DOI:10.1016/S0040-4020(01)80776-6

Reference yield:

Cumene hydroperoxide (80-15-9) → 3-phenyl-oxazolidine (20503-92-8) + Isopropylbenzene (98-82-8) + 2,4,5-trimethylphenol (496-78-6) + 4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one (20483-36-7) + C24H23NO + acetophenone (98-86-2) + isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6)

Guidance literature:

at 80 - 110 ℃; Activation energy; Pyrolysis;

DOI:10.3390/molecules21050562

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → 4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one (20483-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NBS, 2.) Na₂CO₃ / 1.) CCL₄, irradiation, 2.) DMF

2: 1.) Bu₃SnH, Pd(PPh₃)4, NH₄Cl, 2.) NaF / 1.) THF, H₂O, room temperature, 2 h, 2.) EtOAc

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; sodium carbonate; ammonium chloride; sodium fluoride;

DOI:10.1021/jo9505031

upstream raw materials:

(3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one

(E)-4-(1,3,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-but-3-en-2-one

alpha-ionone

4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one

Downstream raw materials:

7,8-dihydro-3,4-dehydro-β-ionol

Refernces

• 1、 Serra, Stefano,Fuganti, Claudio,Brenna, Elisabetta. "Synthesis, olfactory evaluation, and determination of the absolute configuration of the 3,4-didehydroionone stereoisomers". . p. 1110 - 1122. Retrieved 2007/10/03.
• 2、 Andersson,Nilsson,Backvall. "Palladium-catalyzed oxaspirocyclizations". . p. 559 - 572. Retrieved 2007/10/02.