4-Oxocyclohex-2-en-1-yl acetate

Base Information

• Chemical Name: 4-Oxocyclohex-2-en-1-yl acetate
• CAS No.: 50557-37-4
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• DSSTox Substance ID: DTXSID30557714
• Nikkaji Number: J1.434.644I
• Mol file: 50557-37-4.mol

Synonyms:50557-37-4;4-Oxocyclohex-2-en-1-yl acetate;SCHEMBL9414132;DTXSID30557714

Chemical Property of 4-Oxocyclohex-2-en-1-yl acetate

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC(=O)C=C1

Technology Process of 4-Oxocyclohex-2-en-1-yl acetate

There total 11 articles about 4-Oxocyclohex-2-en-1-yl acetate 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: 81.0%

cis-2-cyclohexene-1,4-diol monoacetate (57466-29-2,86210-23-3,86210-32-4,132617-05-1,132617-15-3,136779-08-3) → 4-(acetoxy)cyclohex-2-enone (50557-37-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.5h; Inert atmosphere;

DOI:10.1039/b916506a

Reference yield: 62.0%

Acetic acid (1S,4S)-4-hydroxy-cyclohex-2-enyl ester (57466-29-2,86210-23-3,86210-32-4,132617-05-1,132617-15-3,136779-08-3) → 4-(acetoxy)cyclohex-2-enone (50557-37-4)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 25 ℃; for 16h;

DOI:10.1016/S0040-4039(01)81271-5

Reference yield:

1-methoxycyclohexa-1,4-diene (2886-59-1) → 4-(acetoxy)cyclohex-2-enone (50557-37-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Amberlyst H⁽¹⁺⁾ / CH₂Cl₂ / Ambient temperature

2: 97 percent / m-CPBA / CH₂Cl₂ / 12 h / 0 to 20 deg C

3: 1) AcOH, 2) pyridine / 1) 70 deg C, 12 h, 2) CH₂Cl₂, r.t., 12 h

4: acid

With pyridine; Amberlyst H⁽¹⁺⁾; acetic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/0040-4039(92)88127-Q

upstream raw materials:

rac-3-acetoxycyclohexene

Acetic acid (1S,4S)-4-hydroxy-cyclohex-2-enyl ester

C₁₈H₂₂O₆

1-methoxycyclohexa-1,4-diene