3-(Acetyloxy)-5-phenyl-2-pentanone

Base Information

• Chemical Name: 3-(Acetyloxy)-5-phenyl-2-pentanone
• CAS No.: 1026082-30-3
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.268
• DSSTox Substance ID: DTXSID101295657
• Mol file: 1026082-30-3.mol

Synonyms:3-(Acetyloxy)-5-phenyl-2-pentanone;DTXSID101295657;1026082-30-3

Chemical Property of 3-(Acetyloxy)-5-phenyl-2-pentanone

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 220.109944368
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C(CCC1=CC=CC=C1)OC(=O)C

Technology Process of 3-(Acetyloxy)-5-phenyl-2-pentanone

There total 5 articles about 3-(Acetyloxy)-5-phenyl-2-pentanone 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: 90.0%

(+/-)-1-(2-Phenylethyl)-3-propynyl acetate (100330-45-8) → 4-oxo-1-phenylpentan-3-yl acetate (1026082-30-3)

Guidance literature:

With water; In 1,4-dioxane; at 20 ℃; for 12h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.jorganchem.2020.121136

Reference yield:

5-phenylpent-1-yn-3-ol (99902-35-9,130325-02-9,67648-04-8) → 4-oxo-1-phenylpentan-3-yl acetate (1026082-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / DMAP; pyridine / 0.5 h / 20 °C

2: H₂O / NaAuCl₄*2H₂O / methanol / 2 h / Heating

With pyridine; dmap; water; sodium tetrachloroaurate dihydrate; In methanol; 1: Acetylation / 2: Hydration;

DOI:10.1002/(SICI)1521-3765(19991105)5:11<3252::AID-CHEM3252>3.0.CO;2-D

Reference yield:

5-phenyl-1-trimethylsilylpent-1-yn-3-ol (140149-77-5) → 4-oxo-1-phenylpentan-3-yl acetate (1026082-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

2: 85 percent / DMAP; pyridine / 0.5 h / 20 °C

3: H₂O / NaAuCl₄*2H₂O / methanol / 2 h / Heating

With pyridine; dmap; tetrabutyl ammonium fluoride; water; sodium tetrachloroaurate dihydrate; In tetrahydrofuran; methanol; 1: Desilylation / 2: Acetylation / 3: Hydration;

DOI:10.1002/(SICI)1521-3765(19991105)5:11<3252::AID-CHEM3252>3.0.CO;2-D

upstream raw materials:

(+/-)-1-(2-Phenylethyl)-3-propynyl acetate

3-phenyl-propionaldehyde

5-phenylpent-1-yn-3-ol

5-phenyl-1-trimethylsilylpent-1-yn-3-ol

Downstream raw materials:

5-phenyl-2-pentanone

(+/-)-3-Hydroxy-5-phenyl-2-pentanone