(E)-1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one

Base Information

• Chemical Name: (E)-1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one
• CAS No.: 39872-57-6
• Molecular Formula: C13H20O
• Molecular Weight: 192.301
• European Community (EC) Number: 254-663-8,251-632-0
• DSSTox Substance ID: DTXSID2052075
• Nikkaji Number: J261.465K,J308.518J
• Mol file: 39872-57-6.mol

Synonyms:39872-57-6;(E)-1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one;33673-71-1;EINECS 251-632-0;EINECS 254-663-8;1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one;(E)-1-(2,4,4-trimethylcyclohex-2-en-1-yl)but-2-en-1-one;1-Crotonyl-2,4,4-trimethylcyclohex-2-ene;2-Buten-1-one, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-, (E)-;trans-(2,4,4-Trimethyl-2-cyclohexenyl)-2-butenone;2-Buten-1-one, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-;2-Buten-1-one, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-, (2E)-;SCHEMBL110139;2-buten-1-ona, 1-(2,4,4-trimetil-2-ciclohexen-1-il)-, (2e)-;DTXSID2052075;(E) - 1 - (2,4,4 - trimethyl - 2 - cyclohexen - 1 - yl) - 2 - buten - 1 - one;Ketone, propenyl 2,4,4-trimethyl-2-cyclohexen-1-yl;(2E)-1-(2,4,4-Trimethylcyclohex-2-en-1-yl)but-2-en-1-one, analytical standard;1 - (2,4,4 - trimethyl - 2 - cyclohexen - 1 - yl) - 2 - buten - 1 - one

Chemical Property of (E)-1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one

Chemical Property:

• Vapor Pressure: 5Pa at 20℃
• Boiling Point: 267.1±29.0 °C(Predicted)
• PSA: 17.07000
• Density: 0.898±0.06 g/cm3(Predicted)
• LogP: 3.65820
• Water Solubility.: 119mg/L at 20℃
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 282

Purity/Quality:

99.9% ^*data from raw suppliers

ISODAMASCONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)C1CCC(C=C1C)(C)C
• Isomeric SMILES: C/C=C/C(=O)C1CCC(C=C1C)(C)C

Technology Process of (E)-1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one

There total 5 articles about (E)-1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-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: 65.0%

1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-ethanone (68826-42-6) + acetaldehyde (75-07-0,9002-91-9) → Isodamascone (39872-57-6)

Guidance literature:

1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-ethanone; With ethylmagnesium bromide; N-methylaniline; In toluene; at 25 ℃; for 30h;

acetaldehyde; In toluene; at -5 ℃; for 1h;

With toluene-4-sulfonic acid; In toluene; Heating;

DOI:10.1080/00397910601038988

Reference yield:

1,5,5-trimethylcyclohex-2-ene-1-ol (37779-25-2) → Isodamascone (39872-57-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / hydrogen / Pd/C / ethanol / 1 h / 20 °C / 2585.74 Torr

2.1: p-toluenesulfonic acid / toluene / 2 h / Heating

2.2: zinc chloride / 3 h / 20 - 70 °C

3.1: ethyl magnesium bromide; monomethyl aniline / toluene / 30 h / 25 °C

3.2: toluene / 1 h / -5 °C

3.3: 65 percent / p-toluenesulfonic acid / toluene / Heating

With ethylmagnesium bromide; hydrogen; toluene-4-sulfonic acid; N-methylaniline; palladium on activated charcoal; In ethanol; toluene;

DOI:10.1080/00397910601038988

Reference yield:

1,3,3-trimethyl-cyclohexan-1-ol (79802-79-2) → Isodamascone (39872-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-toluenesulfonic acid / toluene / 2 h / Heating

1.2: zinc chloride / 3 h / 20 - 70 °C

2.1: ethyl magnesium bromide; monomethyl aniline / toluene / 30 h / 25 °C

2.2: toluene / 1 h / -5 °C

2.3: 65 percent / p-toluenesulfonic acid / toluene / Heating

With ethylmagnesium bromide; toluene-4-sulfonic acid; N-methylaniline; In toluene;

DOI:10.1080/00397910601038988

upstream raw materials:

α-damascone

1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-ethanone

acetaldehyde

1,5,5-trimethylcyclohex-2-ene-1-ol

Refernces

• 1、 Klein,Rojahn. "". . p. 3607. Retrieved 1971.