3-(4-Methoxyphenyl)-5-methylisoxazole

Base Information

• Chemical Name: 3-(4-Methoxyphenyl)-5-methylisoxazole
• CAS No.: 61428-21-5
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• DSSTox Substance ID: DTXSID60441374
• Nikkaji Number: J1.116.693H
• Mol file: 61428-21-5.mol

Synonyms:3-(4-methoxyphenyl)-5-methylisoxazole;61428-21-5;Isoxazole, 3-(4-methoxyphenyl)-5-methyl-;SCHEMBL6352561;DTXSID60441374;YKPVFKZCSVBEOV-UHFFFAOYSA-N;BB 0262974;FT-0756946

Chemical Property of 3-(4-Methoxyphenyl)-5-methylisoxazole

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 178

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=NO1)C2=CC=C(C=C2)OC

Technology Process of 3-(4-Methoxyphenyl)-5-methylisoxazole

There total 25 articles about 3-(4-Methoxyphenyl)-5-methylisoxazole 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: 92.0%

C11H12O2S → 3-(4-methoxy-phenyl)-5-methylisoxazole (61428-21-5)

Guidance literature:

C₁₁H₁₂O₂S; With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.0c02216

Reference yield: 81.0%

4-acetoxy-3-acetyl-4-(4-methoxyphenyl)but-3-ene-2-one (104548-27-8) → 3-(4-methoxy-phenyl)-5-methylisoxazole (61428-21-5)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; In methanol; for 6h; Ambient temperature;

Reference yield: 76.0%

1-(4-methoxyphenyl)but-3-en-1-one oxime (904672-46-4) → 3-(4-methoxy-phenyl)-5-methylisoxazole (61428-21-5)

Guidance literature:

With palladium diacetate; silver carbonate; In chlorobenzene; at 70 ℃; for 4h;

DOI:10.1021/ol502246t

upstream raw materials:

2-nitropropene

4-methoxybenzonitrile oxide

4-acetoxy-3-acetyl-4-(4-methoxyphenyl)but-3-ene-2-one

(Z)-3-amino-1-(4-methoxyphenyl)but-2-en-1-one

Refernces

• 1、 Antony P, Mary,Balaji, Gantala L.,Iniyavan, Pethaperumal,Ila, Hiriyakkanavar. "Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N-O Bond Formation". . p. 15422 - 15436. Retrieved 2020/11/30.
• 2、 Raghava, Byregowda,Parameshwarappa, Gangajji,Acharya, Anand,Swaroop, Toreshettahally R.,Rangappa, Kanchugarakoppal S.,Ila, Hiriyakkanavar. "Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity". . p. 1882 - 1892. Retrieved 2015/10/05.