13937-11-6

Basic information

• Product Name: diethyl butylidenepropanedioate
• CAS NO: 13937-11-6
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.2582
• Mol File: 13937-11-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 239.3°C at 760 mmHg
• Flash Point: 104.9°C
• Density: 1.017g/cm³
• Vapor Pressure: 0.0404mmHg at 25°C
• Refractive Index: 1.449
• CAS DataBase Reference: diethyl butylidenepropanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl butylidenepropanedioate(13937-11-6)
• EPA Substance Registry System: diethyl butylidenepropanedioate(13937-11-6)

Safety Data

• Hazardous Substances Data: 13937-11-6(Hazardous Substances Data)

Upstream product

• 109-73-9 N-butylamine 
• 105-53-3 diethyl malonate 
• 123-72-8 butyraldehyde 

Downstream Products

• 93541-60-7 ((1-Cyclohexen-⁽¹⁾-yl)-butyl)-malonsaeurediethylester 
• 1359859-30-5 C₂₄H₃₁NO₄ 
• 71083-06-2 ethyl 8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 51703-97-0 (R)-(-)-2-methylhexanoic acid 
• 62243-57-6 2-methyl-3-hexenoic acid 
• 101892-15-3 1-Phenyl-hexen-⁽³⁾-dicarbonsaeure-(2,2)-diaethylester 
• 59771-20-9 (1-phenyl-butyl)-malonic acid diethyl ester 
• 117-47-5 diethyl (1-methylbutyl)malonate 
• 133-08-4 diethyl butylmalonate 

Relevant articles and documents

Synthesis of novel spirocyclopropylmalonates and barbiturates

Alkylidenemalonates have been subjected to dichlorocyclopropanation to produce novel spiro-gem-dichlorocyclopropylmalonates in quantitative yields. The latter have been reacted with urea in the presence of sodium ethoxide to produce the corresponding barbiturates in 80–95% yields. The cleavage of the spiro-gem-dichlorocyclopropylmalonate carbocycle with ethanol with the aid of aluminum chloride has led to ethyl ethers, while carbocycle expansion with isobutyraldehyde has afforded polysubstituted tetrahydrofurans. The prepared compounds have been structurally characterized in detail by 1H and 13C NMR spectroscopy.

First model reactions towards the synthesis of sarain A core skeleton based upon a biogenetic scenario

Sarain A is a complex macrocyclic marine alkaloid extracted from sponges of the order Haplosclerida. It is likely that this alkaloid shares a common origin with manzamine alkaloids, also extracted from sponges of the same order. In this paper, new concepts concerning this origin are presented and constitute the basis for a synthetic strategy. A preliminary evaluation of this strategy is presented and leads, as a first result, to a five-step access to the bicyclic intermediate 43. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

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.

Method for regio- and stereoselective synthesis of (E)-Β,γ- unsaturated acids from aldehydes under solvent-free conditions

Synthesis of (E)-β,-γunsaturated acids from aldehydes with malonic acid has been explored under solvent-free conditions. The modified Knoevenagel condensation reaction with N-methyl morpholine (NMM) as catalyst exhibits highly β,-γ regioselectivity and exclusively E-stereoselectivity. A mechanism accounting for both regio- and stereoselectivity has been proposed and preliminarily studied. Copyright Taylor & Francis Group, LLC.