Methyl 5-(3-formyl-4-nitrophenoxy)pentanoate

Base Information

• Chemical Name: Methyl 5-(3-formyl-4-nitrophenoxy)pentanoate
• CAS No.: 105728-03-8
• Molecular Formula: C13H15NO6
• Molecular Weight: 281.265
• DSSTox Substance ID: DTXSID601258545
• Mol file: 105728-03-8.mol

Synonyms:methyl 5-(3-formyl-4-nitrophenoxy)pentanoate;105728-03-8;DTXSID601258545

Chemical Property of Methyl 5-(3-formyl-4-nitrophenoxy)pentanoate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 281.08993720
• Heavy Atom Count: 20
• Complexity: 340

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CCCCOC1=CC(=C(C=C1)[N+](=O)[O-])C=O

Technology Process of Methyl 5-(3-formyl-4-nitrophenoxy)pentanoate

There total 1 articles about Methyl 5-(3-formyl-4-nitrophenoxy)pentanoate 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: 98.0%

5-bromovaleric acid methyl ester (5454-83-1) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 5-(3-Formyl-4-nitro-phenoxy)-pentanoic acid methyl ester (105728-03-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/jm00385a012

Reference yield: 75.0%

5-(3-Formyl-4-nitro-phenoxy)-pentanoic acid methyl ester (105728-03-8) → 5-(3-formyl-4-nitrophenyl)oxypentanoic acid (105728-07-2)

Guidance literature:

With potassium hydroxide;

DOI:10.1021/jm00385a012

Reference yield:

5-(3-Formyl-4-nitro-phenoxy)-pentanoic acid methyl ester (105728-03-8) → N-cyclohexyl-N-methyl-5-(2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)-oxypentanamide (94192-82-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / aq. KOH

2: oxalyl chloride / benzene; dimethylformamide / 0.5 h

3: aq. Na₂CO₃ / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) AcONa / ethanol / 0.5 h

5: NaBH₃CN / ethanol / 3 h

6: H₂ / 10percent Pd/C / ethanol

7: 2.) conc. aq. NH₃ / 1.) EtOH, RT, overnight, 2.) EtOH, RT, 30 min

With potassium hydroxide; ammonium hydroxide; oxalyl dichloride; hydrogen; sodium acetate; sodium cyanoborohydride; sodium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00385a012

upstream raw materials:

5-bromovaleric acid methyl ester

2-nitro-5-hydroxybenzaldehyde

Downstream raw materials:

5-(3-formyl-4-nitrophenyl)oxypentanoic acid

5-(3-Formyl-4-nitro-phenoxy)-pentanoic acid cyclohexyl-methyl-amide

N-cyclohexyl-N-methyl-5-(2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)-oxypentanamide

5-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]quinolin-7-yloxy)-pentanoic acid cyclohexyl-methyl-amide