(4R)-4-(4-nitrophenyl)pentan-2-one

Base Information

• Chemical Name: (4R)-4-(4-nitrophenyl)pentan-2-one
• CAS No.: 90280-93-6
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.229
• DSSTox Substance ID: DTXSID20531548
• Wikidata: Q82403494
• Mol file: 90280-93-6.mol

Synonyms:(4R)-4-(4-nitrophenyl)pentan-2-one;90280-93-6;DTXSID20531548

Chemical Property of (4R)-4-(4-nitrophenyl)pentan-2-one

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)C)C1=CC=C(C=C1)[N+](=O)[O-]
• Isomeric SMILES: C[C@H](CC(=O)C)C1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of (4R)-4-(4-nitrophenyl)pentan-2-one

There total 3 articles about (4R)-4-(4-nitrophenyl)pentan-2-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:

3-penten-2-ol (1569-50-2) + 4-nitrobenzenediazonium tetrafluoroborate (456-27-9) → (R)-4-(4-nitrophenyl)pentan-2-one (90280-93-6) + 4-(4-nitrophenyl)pentan-2-one (104023-01-0)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,5-bis(3-(trifluoromethyl)phenyl)penta-1,4-dien-3-one; (S)-3,3'-bis(2,4,6-triisopropylphenyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; sodium carbonate; dimethyl sulfoxide; In diethyl ether; at 0 ℃; for 12h; Overall yield = 80 percent; enantioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.1c00152

Reference yield:

1-methyl-3-phenyl-butanal (17913-10-9) → (R)-4-(4-nitrophenyl)pentan-2-one (90280-93-6)

Guidance literature:

DOI:10.1016/S0040-4039(00)99934-9

Reference yield:

(1R)-1-(4-nitrophenyl)ethanol (6531-13-1,96156-72-8,99531-06-3,58287-18-6) + acetoacetic acid methyl ester (105-45-3) → 1-[4-nitrophenyl]-1-ethanol (6531-13-1) + (R)-4-(4-nitrophenyl)pentan-2-one (90280-93-6) + 4-(4-nitrophenyl)pentan-2-one (104023-01-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; Mechanism;

DOI:10.1016/S0040-4039(00)99934-9

upstream raw materials:

1-methyl-3-phenyl-butanal

(1R)-1-(4-nitrophenyl)ethanol

acetoacetic acid methyl ester

3-penten-2-ol