3-(4-Methoxyphenyl)-4,5-dihydronaphtho[1,2-c][1,2]oxazole

Base Information

• Chemical Name: 3-(4-Methoxyphenyl)-4,5-dihydronaphtho[1,2-c][1,2]oxazole
• CAS No.: 24097-25-4
• Molecular Formula: C₁₈H₁₅NO₂
• Molecular Weight: 277.323
• NSC Number: 133089
• DSSTox Substance ID: DTXSID40299835
• Nikkaji Number: J1.438.660B
• Wikidata: Q82042509
• Mol file: 24097-25-4.mol

Synonyms:24097-25-4;3-(4-Methoxyphenyl)-4,5-dihydronaphtho[1,2-c]isoxazole;3-(4-methoxyphenyl)-4,5-dihydronaphtho[1,2-c][1,2]oxazole;NSC133089;DTXSID40299835;NSC-133089

Chemical Property of 3-(4-Methoxyphenyl)-4,5-dihydronaphtho[1,2-c][1,2]oxazole

Chemical Property:

• Vapor Pressure: 4.24E-09mmHg at 25°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 277.110278721
• Heavy Atom Count: 21
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=C3CCC4=CC=CC=C4C3=NO2

Technology Process of 3-(4-Methoxyphenyl)-4,5-dihydronaphtho[1,2-c][1,2]oxazole

There total 3 articles about 3-(4-Methoxyphenyl)-4,5-dihydronaphtho[1,2-c][1,2]oxazole 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: 68.0%

1-tetralone oxime (68253-36-1) + ethyl 4-methoxybenzoate (94-30-4) → 3-(4-methoxy-phenyl)-4,5-dihydro-naphtho[1,2-c]isoxazole (24097-25-4)

Guidance literature:

1-tetralone oxime; With lithium diisopropyl amide; In tetrahydrofuran;

ethyl 4-methoxybenzoate; In tetrahydrofuran; for 1.5h;

With hydrogenchloride; for 1h; Heating;

DOI:10.1080/00397910008086979

Reference yield:

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 3-(4-methoxy-phenyl)-4,5-dihydro-naphtho[1,2-c]isoxazole (24097-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / NH₂OH / ethanol; H₂O / Heating

2.1: LDA / tetrahydrofuran

2.2: tetrahydrofuran / 1.5 h

2.3: 68 percent / 3N HCl / 1 h / Heating

With hydroxylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; water; 1.1: Condensation / 2.1: Metallation / 2.2: Condensation / 2.3: Cyclization;

DOI:10.1080/00397910008086979

Reference yield:

1-tetralone oxime (3349-64-2,68253-36-1,100485-58-3) + methyl 4-methoxybenzoate (121-98-2) → 3-(4-methoxy-phenyl)-4,5-dihydro-naphtho[1,2-c]isoxazole (24097-25-4)

Guidance literature:

Multistep reaction; (i) nBuLi, THF, (ii) /BRN= 2208571/, (iii) aq. HCl;

DOI:10.1021/jo00831a020

upstream raw materials:

1-tetralone oxime

methyl 4-methoxybenzoate

1-tetralone oxime

ethyl 4-methoxybenzoate