17669-30-6

Basic information

• Product Name: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester
• Synonyms: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester
• CAS NO: 17669-30-6
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.246
• Mol File: 17669-30-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 371.3°Cat760mmHg
• Flash Point: 165.7°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester(17669-30-6)
• EPA Substance Registry System: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester(17669-30-6)

Safety Data

• Hazardous Substances Data: 17669-30-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H13NO5/c1-17-12(15)9-10(8-6-4-3-5-7-8)14-19-11(9)13(16)18-2/h3-7,9,11H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 99972-90-4 (+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid 
• 67-56-1 methanol 
• 17669-30-6 Z-dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate 
• 124-41-4 sodium methylate 
• 99972-90-4 (+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5c-dicarboxylic acid 
• 932-90-1 Benzaldoxime 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 698-16-8 benzohydroximoyl chloride 
• 20080-27-7 3-phenyl-4,5-dihydro-isoxazole-4r,5c-dicarboxylic acid dibenzyl ester 
• 873-67-6 benzonitrile oxide 
• 932-90-1 syn-benzaldehyde oxime 
• 624-49-7 dimethylfumarate 
• 611-73-4 Benzoylformic acid 

Downstream Products

• 99972-90-4 (+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid 
• 17669-30-6 dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate 
• 99972-90-4 (+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5c-dicarboxylic acid 
• 4872-58-6 3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid 
• 100-47-0 benzonitrile 
• 35053-78-2 3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid diamide 

Relevant articles and documents

Electrochemical Synthesis of Isoxazolines: Method and Mechanism

An electrochemical method for the green and practical synthesis of a broad range of substituted isoxazoline cores is presented. Both aryl and more challenging alkyl aldoximes are converted to the desired isoxazoline in an electrochemically enabled regio- and diastereoselective reaction with electron-deficient alkenes. Additionally, in-situ reaction monitoring methods compatible with electrochemistry equipment have been developed in order to probe the reaction pathway. Supporting analyses from kinetic (time-course) modelling and density functional theory support a stepwise, radical-mediated mechanism, and discounts hypothesised involvement of closed shell [3+2] cycloaddition pathways.

Visible-light-mediated generation of nitrile oxides for the photoredox synthesis of isoxazolines and isoxazoles

Visible-light photoredox catalysis enables the synthesis of biologically relevant isoxazolines and isoxazoles from hydroxyimino acids. The process shows broad functional group compatibility and mechanistic and computational studies support a visible-light-mediated generation of nitrile oxides by two sequential oxidative single electron transfer processes.

Conversion of oximes to carbonyl compounds by triscetylpyridinium tetrakis(oxodiperoxotungsto) phosphate (PCWP)-mediated oxidation with hydrogen peroxide

Aromatic and aliphatic oximes have been deoximated in chloroform-water to the corresponding aldehydes with dilute hydrogen peroxide and triscetylpyridinium tetrakis (oxodiperoxotungsto) phosphate as catalyst. The presence of dipolarophiles in the reaction mixtures allows a competitive reaction that converts oximes into isoxazole and isoxazoline derivatives via the intermediate formation of nitrile oxide species.