(2E)-1-[3-(Acetyloxy)-2,6,6-trimethyl-1-cyclohexen-1-YL]-2-buten-1-one

Base Information

• Chemical Name: (2E)-1-[3-(Acetyloxy)-2,6,6-trimethyl-1-cyclohexen-1-YL]-2-buten-1-one
• CAS No.: 945426-71-1
• Molecular Formula: C15H22O3
• Molecular Weight: 250.338
• Hs Code.: 2915390090
• Mol file: 945426-71-1.mol

Synonyms:945426-71-1;(2E)-1-[3-(ACETYLOXY)-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL]-2-BUTEN-1-ONE;4-Acetoxy-|A-damascone;[3-[(E)-but-2-enoyl]-2,4,4-trimethylcyclohex-2-en-1-yl] acetate;4-Acetoxy-?-damascone;4-Acetoxy- beta -damascone;AKOS025295950;DB-252175;(E)-3-(But-2-enoyl)-2,4,4-trimethylcyclohex-2-en-1-yl acetate;3-[(2E)-2-butenoyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate

Chemical Property of (2E)-1-[3-(Acetyloxy)-2,6,6-trimethyl-1-cyclohexen-1-YL]-2-buten-1-one

Chemical Property:

• PSA: 43.37000
• LogP: 3.19980
• Solubility.: Chloroform
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 250.15689456
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

98%min ^*data from raw suppliers

4-ACETOXY-BETA-DAMASCONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)C1=C(C(CCC1(C)C)OC(=O)C)C
• Isomeric SMILES: C/C=C/C(=O)C1=C(C(CCC1(C)C)OC(=O)C)C
• Uses: Fragrant compound

Technology Process of (2E)-1-[3-(Acetyloxy)-2,6,6-trimethyl-1-cyclohexen-1-YL]-2-buten-1-one

There total 9 articles about (2E)-1-[3-(Acetyloxy)-2,6,6-trimethyl-1-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: 78.0%

C16H26O4 (945426-70-0) → (E)-3-(but-2-enoyl)-2,4,4-trimethylcyclohex-2-en-1-yl acetate (945426-71-1)

Guidance literature:

With aluminum oxide; In diethyl ether; at 20 ℃; for 12h;

DOI:10.1080/00397910701196546

Reference yield:

4-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2-methoxybutane (945426-65-3) → (E)-3-(but-2-enoyl)-2,4,4-trimethylcyclohex-2-en-1-yl acetate (945426-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH₂Cl₂ / 8 h / 20 °C

1.2: 220 mg / sulfuric acid / H₂O; diethyl ether / 6 h / 20 °C

2.1: pyridine / diethyl ether / 0 - 20 °C

3.1: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 20 °C

4.1: 78 percent / active neutral alumina / diethyl ether / 12 h / 20 °C

With pyridine; aluminum oxide; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In diethyl ether; dichloromethane;

DOI:10.1080/00397910701196546

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → (E)-3-(but-2-enoyl)-2,4,4-trimethylcyclohex-2-en-1-yl acetate (945426-71-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: isopropenyl acetate; p-toluenesulfonic acid monohydrate / 24 h / Heating

1.2: NaBH₄ / aq. ethanol / 1.5 h / Heating

2.1: 96 percent / sodium hydride / dimethylformamide / 0 - 20 °C

3.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH₂Cl₂ / 8 h / 20 °C

3.2: 220 mg / sulfuric acid / H₂O; diethyl ether / 6 h / 20 °C

4.1: pyridine / diethyl ether / 0 - 20 °C

5.1: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 20 °C

6.1: 78 percent / active neutral alumina / diethyl ether / 12 h / 20 °C

With pyridine; aluminum oxide; Isopropenyl acetate; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/00397910701196546

upstream raw materials:

C₁₆H₂₆O₄

C₁₄H₂₆O₃

C₁₆H₂₈O₄

C₁₄H₂₄O₃

Downstream raw materials:

Damascenon