Diethyl (4-hydroxy-2-oxo-4-phenylbutyl)phosphonate

Base Information

• Chemical Name: Diethyl (4-hydroxy-2-oxo-4-phenylbutyl)phosphonate
• CAS No.: 113847-99-7
• Molecular Formula: C14H21O5P
• Molecular Weight: 300.292
• DSSTox Substance ID: DTXSID30550301
• Nikkaji Number: J354.905D
• Mol file: 113847-99-7.mol

Synonyms:113847-99-7;1-diethoxyphosphoryl-4-hydroxy-4-phenylbutan-2-one;4-Hydroxy-4-phenyl-2-oxobutylphosphonic acid diethyl ester;Diethyl (4-hydroxy-2-oxo-4-phenylbutyl)phosphonate;DTXSID30550301;2-HYDROXY-2-PHENYL-1'-DIETHOXYPHOSPHORYLETHYLMETHYLKETONE

Chemical Property of Diethyl (4-hydroxy-2-oxo-4-phenylbutyl)phosphonate

Chemical Property:

• PSA: 82.64000
• LogP: 2.94530
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 300.11266076
• Heavy Atom Count: 20
• Complexity: 329

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOP(=O)(CC(=O)CC(C1=CC=CC=C1)O)OCC

Technology Process of Diethyl (4-hydroxy-2-oxo-4-phenylbutyl)phosphonate

There total 5 articles about Diethyl (4-hydroxy-2-oxo-4-phenylbutyl)phosphonate 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: 80.0%

(5-Phenyl-4,5-dihydro-isoxazol-3-ylmethyl)-phosphonic acid diethyl ester (107487-00-3) → (4-Hydroxy-2-oxo-4-phenyl-butyl)-phosphonic acid diethyl ester (113847-99-7)

Guidance literature:

With hydrogen; boric acid; Raney Ni (W-2); In ethanol; water; for 12h; under 760 Torr; Ambient temperature;

DOI:10.1246/bcsj.60.2463

Reference yield:

(2-oxoethyl)phosphonic acid diethyl ester (1606-75-3) → (4-Hydroxy-2-oxo-4-phenyl-butyl)-phosphonic acid diethyl ester (113847-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / aq. hydroxylamine hydrochloride / ethanol / 11.5 h / Ambient temperature

2: 1.) NBS; 2.) triethylamine / 1.) DMF, -20 deg C, 1 h, 0 deg C, 30 min; 2.) DMF, Et₂O, RT, 18 h

3: 80 percent / boric acid, H₂ / Raney Ni (W-2) / ethanol; H₂O / 12 h / 760 Torr / Ambient temperature

With N-Bromosuccinimide; hydroxylamine hydrochloride; hydrogen; boric acid; triethylamine; Raney Ni (W-2); In ethanol; water;

DOI:10.1246/bcsj.60.2463

Reference yield:

N-<2-(diethoxyphosphoryl)ethylidene>hydroxylamine (110841-50-4) → (4-Hydroxy-2-oxo-4-phenyl-butyl)-phosphonic acid diethyl ester (113847-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NBS; 2.) triethylamine / 1.) DMF, -20 deg C, 1 h, 0 deg C, 30 min; 2.) DMF, Et₂O, RT, 18 h

2: 80 percent / boric acid, H₂ / Raney Ni (W-2) / ethanol; H₂O / 12 h / 760 Torr / Ambient temperature

With N-Bromosuccinimide; hydrogen; boric acid; triethylamine; Raney Ni (W-2); In ethanol; water;

DOI:10.1246/bcsj.60.2463

upstream raw materials:

(5-Phenyl-4,5-dihydro-isoxazol-3-ylmethyl)-phosphonic acid diethyl ester

Diethyl (2-oxopropyl)phosphonate

benzaldehyde

styrene

Downstream raw materials:

1,5-diphenyl-1,4-pentadien-3-one

(E)-benzalacetone

diethyl 4-butyryloxy-2-oxo-4-phenylbutylphosphonate

(4R)-diethyl 4-hydroxy-2-oxo-4-phenylbutylphosphonate