4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester
• CAS No.: 17669-30-6
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.25
• Mol file: 17669-30-6.mol

Synonyms:3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid dimethyl ester;2-Isoxazoline-4,5-dicarboxylic acid,3-phenyl-,dimethyl ester,cis;3-Phenyl-2-isoxazolin-trans-4,5-dicarbonsaeuredimethylester;4,5-Isoxazoledicarboxylic acid,4,5-dihydro-3-phenyl-,dimethyl ester,cis;

Chemical Property of 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester

Chemical Property:

• Vapor Pressure: 1.04E-05mmHg at 25°C
• Boiling Point: 371.3°Cat760mmHg
• Flash Point: 165.7°C
• PSA: 74.19000
• Density: 1.3g/cm³
• LogP: 0.18730

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester

There total 25 articles about 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester 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: 78.0%

(Z)-2-(hydroxyimino)-2-phenylacetic acid (25327-36-0) + 1,4-dimethyl but-2-enedioate (23055-10-9) → dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate (17669-30-6,17669-31-7,108198-94-3)

Guidance literature:

With Oxone; tris(2,2'-bipyridyl)ruthenium dichloride; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 18h; Sealed tube; Irradiation;

DOI:10.1039/c6cc06029c

Reference yield: 76.0%

1-nitro-1-phenylmethane (622-42-4) + dimethylfumarate (624-49-7) → dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate (17669-30-6,17669-31-7,108198-94-3)

Guidance literature:

With sodium methylate; acetyl chloride; In N,N-dimethyl acetamide; for 16h; Ambient temperature;

DOI:10.1248/cpb.28.3296

Reference yield: 68.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + benzohydroximoyl chloride (698-16-8) → Z-dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate (17669-30-6,17669-31-7,108198-94-3)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.6b03103

upstream raw materials:

benzonitrile oxide

dimethylfumarate

diazomethane

(+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid

Downstream raw materials:

(+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid

dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate

(+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5c-dicarboxylic acid

3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid diamide

Refernces

• 1、 Svejstrup, Thomas D.,Zawodny, Wojciech,Douglas, James J.,Bidgeli, Damon,Sheikh, Nadeem S.,Leonori, Daniele. "Visible-light-mediated generation of nitrile oxides for the photoredox synthesis of isoxazolines and isoxazoles". supporting information. p. 12302 - 12305. Retrieved 2016/10/22.
• 2、 Romanski, Jan,Nowak, Piotr,Maksymiuk, Anna,Chapuis, Christian,Jurczak, Janusz. "Diastereoselective 1,3-dipolar cycloadditions of both electronically modified phenyl-nitrile oxides and stilbenes". . p. 23105 - 23118. Retrieved 2013/11/19.