85068-37-7

Basic information

• Product Name: diethyl (1-naphthylmethyl)(tetrahydrofurfuryl)malonate
• Synonyms: diethyl (1-naphthylmethyl)(tetrahydrofurfuryl)malonate;(1-Naphthalenylmethyl)[(tetrahydrofuran)-2-ylmethyl]propanedioic acid diethyl ester;Einecs 285-299-8
• CAS NO: 85068-37-7
• Molecular Formula: C₂₃H₂₈O₅
• Molecular Weight: 384.46542
• EINECS: 285-299-8
• Mol File: 85068-37-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 500.4°Cat760mmHg
• Flash Point: 215.9°C
• Appearance: /
• Density: 1.148g/cm³
• Vapor Pressure: 3.82E-10mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: diethyl (1-naphthylmethyl)(tetrahydrofurfuryl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (1-naphthylmethyl)(tetrahydrofurfuryl)malonate(85068-37-7)
• EPA Substance Registry System: diethyl (1-naphthylmethyl)(tetrahydrofurfuryl)malonate(85068-37-7)

Safety Data

• Hazardous Substances Data: 85068-37-7(Hazardous Substances Data)

Usage

Uses

(1-Naphthalenylmethyl)[(tetrahydro-2-furanyl)methyl]-propanedioic Acid Diethyl Ester is an intermediate in synthesizing Nafronyl (N215000), which is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication.

InChI:InChI=1/C23H28O5/c1-3-23(21(24)26-4-2,15-19-12-8-14-27-19)22(25)28-16-18-11-7-10-17-9-5-6-13-20(17)18/h5-7,9-11,13,19H,3-4,8,12,14-16H2,1-2H3

Upstream product

• 37136-39-3 diethyl 2-((tetrahydrofuran-2-yl)methyl)malonate 
• 86-52-2 1-Chloromethylnaphthalene 
• 1192-30-9 tetrahydrofurfuryl bromide 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 98-01-1 furfural 
• 17448-96-3 ethyl 2-carbethoxy-3-(2-furanyl)propenoate 
• 105-53-3 diethyl malonate 

Downstream Products

• 113527-39-2 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid 
• 25379-26-4 acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 
• 31329-57-4 nafronyl 
• 77713-52-1 bis(2-diethylaminoethyl) 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate 

Relevant articles and documents

2-DIETHYLAMINOETHYL ESTERS OF 1,3-DISUBSTITUTED PROPANE-2-CARBOXYLIC ACIDS

Alkaline hydrolysis of diethyl 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate (IV) gave the crude acid V which was purified via the dipotassium salt and was obtained as the homogenous higher melting crystal form.Its thermic decarboxylation yielded the acid II as a mixture of two racemates (38:62); crystallization led to almost homogenous racemate B (10:90).Reaction of the sodium salt of II with dimethyl sulfate in methanol gave the methyl ester III which afforded by ester exchange with 2-diethylaminoethanol the ester I (mixture of two racemates 34:66). 2-Diethylaminoethyl 1,3-bis(1-naphthyl)propane-2-carboxylate (VII) was synthetized in three steps from diethyl (1-naphthylmethyl)malonate.Ester X was obtained from 1,3-bis(tetrahydro-2-furyl)propane-2-carboxylic acid by treatment with 2-diethylaminoethyl chloride in boiling 2-propanol in the presence of potassium carbonate.The acid V gave similarly the diester VI. 2-Diethylaminoethyl esters I, VI, VII, and X were transformed to the hydrogen oxalates.Pharmacological screening showed for the diester VI hypotensive, spasmolytic, antiarrhythmic, and antitussic activity.