6771-54-6

Basic information

• Product Name: 3-Methoxybenzylidenemalonic acid diethyl ester
• Synonyms: (3-Methoxybenzylidene)malonic acid diethyl ester;3-Methoxybenzylidenemalonic acid diethyl ester;2-[(3-Methoxyphenyl)Methylene]-propanedioic Acid 1,3-Diethyl Ester;Diethyl M-Methoxybenzylidene Malonate;NSC 637151
• CAS NO: 6771-54-6
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.3
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6771-54-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Solubility: Ether, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3-Methoxybenzylidenemalonic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxybenzylidenemalonic acid diethyl ester(6771-54-6)
• EPA Substance Registry System: 3-Methoxybenzylidenemalonic acid diethyl ester(6771-54-6)

Safety Data

• Hazardous Substances Data: 6771-54-6(Hazardous Substances Data)

Usage

Description

3-Methoxybenzylidenemalonic acid diethyl ester is an organic compound characterized by its yellow oil appearance. It is a derivative of malonic acid with an ester functional group and a methoxybenzylidene moiety attached to the benzene ring.

Uses

Used in Pharmaceutical Industry:
3-Methoxybenzylidenemalonic acid diethyl ester is used as an intermediate in the synthesis of rac Enterolactone (E558950), a compound with potential pharmaceutical applications. Its role in the preparation process is crucial for the development of this compound, which may have therapeutic benefits.
Used in Chemical Synthesis:
As a versatile organic compound, 3-Methoxybenzylidenemalonic acid diethyl ester can be utilized in various chemical synthesis processes. Its unique structure allows it to be a valuable building block for creating a range of other organic molecules, potentially leading to new applications in different industries.

Upstream product

• 5071-96-5 3-METHOXYBENZYLAMINE 
• 105-53-3 diethyl malonate 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 22621-50-7 (3-methoxy-benzylidene)-malonic acid 
• 6099-04-3 trans-3-methoxycinnamic acid 
• 861591-17-5 (2,α-dibromo-5-methoxy-benzylidene)-malonic acid 
• 77094-97-4 diethyl 2-(3-methoxyphenyl)cyclopropane-1,1-dicarboxylate 
• 1217022-72-4 ethyl 2-carbethoxy-3-cyano-3-(3-methoxyphenyl)propionate 
• 1253518-09-0 C₂₀H₂₉NO₅ 
• 1435060-13-1 (S)-ethyl 2-ethoxycarbonyl-3-(3-indolyl)-3-(m-methoxylphenyl)Propanoate 
• 61227-48-3 [(3-methoxyphenyl)methyl]propanedioic acid diethyl ester 

Relevant articles and documents

Programmed Sequential Additions to Halogenated Mucononitriles

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,1,3-benzothiadiazole and undergo conjugate addition/elimination reactions with both nitrogen (40-95% yield) and carbon nucleophiles (72-93% yield). Secondary amines undergo monosubstitutions, while carbon nucleophiles are added twice. The sequence of addition of the nucleophiles could be controlled to give mixed addition products. The multicomponent coupling products could then be converted to natural product like motifs using intramolecular cyclization reactions.

Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds

An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.

Lipase-Catalysed Addition of Pyrrolidine to Chalcone and Benzylidene Malonate Derivatives

The porcine pancreas lipase (PPL) type II catalyzes the aminolysis of benzylidene malonates by regiospecific amidation of substrates and afforded the Z-isomer; no E-isomer or diamide byproducts were observed. PPL also catalyzes Michael addition of acetophenone to various derivatives of chalcones.