2-Cyclohexen-1-one, 3,4,4-trimethyl-

Base Information

• Chemical Name: 2-Cyclohexen-1-one, 3,4,4-trimethyl-
• CAS No.: 17299-41-1
• Molecular Formula: C9H14 O
• Molecular Weight: 138.21
• Hs Code.: 2914299000
• DSSTox Substance ID: DTXSID60169485
• Nikkaji Number: J2.283G
• Wikidata: Q83039199
• Mol file: 17299-41-1.mol

Synonyms:17299-41-1;2-Cyclohexen-1-one, 3,4,4-trimethyl-;3,4,4-trimethylcyclohex-2-enone;3,4,4-trimethylcyclohex-2-en-1-one;1,6,6-Trimethylcyclohexene-3-one;3,4,4-trimethyl-cyclohex-2-enone;3,4,4-TRIMETHYL-2-CYCLOHEXEN-1-ONE;SCHEMBL857338;DTXSID60169485;3,4,4-trimethyl-cyclohex-2-en-1-one;3,4,4-Trimethyl-2-cyclohexen-1-one #

Chemical Property of 2-Cyclohexen-1-one, 3,4,4-trimethyl-

Chemical Property:

• Vapor Pressure: 0.136mmHg at 25°C
• Refractive Index: 1.4889 (estimate)
• Boiling Point: 217°C at 760 mmHg
• Flash Point: 75.7°C
• PSA: 17.07000
• Density: 0.905g/cm³
• LogP: 2.32180
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 138.104465066
• Heavy Atom Count: 10
• Complexity: 187

Purity/Quality:

3,4,4-Trimethylcyclohex-2-enone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)CCC1(C)C

Technology Process of 2-Cyclohexen-1-one, 3,4,4-trimethyl-

There total 19 articles about 2-Cyclohexen-1-one, 3,4,4-trimethyl- 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: 66.0%

3-methyl-butan-2-one (563-80-4) + methyl vinyl ketone (78-94-4,25038-87-3) → 3,6,6-trimethyl-2-cyclohexen-1-one (23438-77-9) + Isocampherphoron (17299-41-1)

Guidance literature:

With toluene-4-sulfonic acid; for 10h; Yields of byproduct given; Heating;

Reference yield:

5-Methyl-5-(phenylthio)-2-hexanone (130660-15-0) → Isocampherphoron (17299-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / p-toluenesulfonic acid / benzene / 16 h / Heating

2: 1.) lithium 4,4'-di-tert-butylbiphenylide, 2.) CuBr*Me₂S / 1.) THF, 30 min, 2.) THF, -78 deg C, 3 h, 3.) THF, -78 deg C, 12 h

3: 1.) p-toluenesulfonic acid, 2.) 5percent KOH, 40percent n-Bu₄NOH / 1.) acetone, water, reflux 7 h, 2.) THF, water, reflux, 14 h

With potassium hydroxide; copper(I) bromide dimethylsulfide complex; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; tetra(n-butyl)ammonium hydroxide; toluene-4-sulfonic acid; In benzene;

DOI:10.1016/S0040-4020(01)85652-0

Reference yield:

β-campholenonitrile (1727-76-0) → Isocampherphoron (17299-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1: aq.-ethanolic NaOH-solution

2: aq. NaOH solution; potassium permanganate

3: lead (IV)-acetate; acetic acid / Erhitzen des mit wss. H₂SO₄ versetzten Reaktionsgemisches mit Wasser-Dampf

With lead(IV) acetate; sodium hydroxide; potassium permanganate; acetic acid;

DOI:10.1021/jo01196a005

upstream raw materials:

(2,3,3-trimethyl-cyclopent-1-enyl)-acetic acid

3-isobutyloxy-6,6-dimethylcyclohex-2-en-1-one

lead(IV) tetraacetate

acetic acid

Downstream raw materials:

2,2-dimethylglutaric acid

3,4,4-trimethylcyclohex-2-enamine

Refernces

• 1、 Witteveen, Jan G.,Weerdt, Anton J. A. van der. "Synthesis of three new compounds structurally related to damascone and ionone". . p. 383 - 386. Retrieved 2007/10/02.