759-58-0

Basic information

• Product Name: ETHYL 2-CYANO-3-METHYLCROTONATE
• Synonyms: Crotonic acid, 2-cyano-3-methyl-, ethyl ester;Ethyl isopropylidene(cyano)acetate;TIMTEC-BB SBB007715;ETHYL 2-CYANO-3-METHYLCROTONATE;ETHYL 2-CYANO-3-METHYL-2-BUTENOATE;Ethyl 2-cyano-3-methylbutanoate;2-cyano-3-methylcrotonic acid ethyl ester;Ethyl 2-cyano-3-methyl-2-butanoate
• CAS NO: 759-58-0
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18
• Product Categories: Small molecule;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 759-58-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: ca 20℃
• Boiling Point: 98-99 °C1 mm Hg(lit.)
• Flash Point: 224 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 1.014 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00386mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• BRN: 507839
• CAS DataBase Reference: ETHYL 2-CYANO-3-METHYLCROTONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CYANO-3-METHYLCROTONATE(759-58-0)
• EPA Substance Registry System: ETHYL 2-CYANO-3-METHYLCROTONATE(759-58-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 759-58-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3418, 1949 DOI: 10.1021/ja01178a044

General Description

Ethyl 2-cyano-3-methyl-2-butenoate, a highly activated acceptor, undergoes the phospha-Michael reaction upon trituration of the reagents at room temperature.

InChI:InChI=1/C8H11NO2/c1-4-11-8(10)7(5-9)6(2)3/h4H2,1-3H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 67-64-1 acetone 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 593-51-1 methylamine hydrochloride 
• 62-53-3 aniline 
• 109-89-7 diethylamine 
• 110-89-4 piperidine 
• 25468-53-5 ethyl (2Z)-2-cyano-3-ethoxypent-2-enoate 
• 186581-53-3 diazomethane 
• 686-33-9 ethyl 2-cyanobut-2-enoate 

Downstream Products

• 6333-05-7 2-cyano-3,3-dimethyl-4-phenyl-butyric acid ethyl ester 
• 3213-49-8 ethyl 2-isopropylcyanoacetate 
• 3302-16-7 3,3-dimethyl-butyronitrile 
• 141-82-2 malonic acid 
• 759-21-7 2-cyano-3-methylbut-2-enoic acid 
• 51116-82-6 2-Cyan-3.3-dimethyl-4-p-tolylvaleriansaeure 
• 91690-68-5 2-cyano-3,3-dimethyl-heptanoic acid ethyl ester 
• 1354655-30-3 ethyl 2-cyano-3-[bis(4-methylphenyl)phosphinyl]-3-methylbutanoate 
• 1267054-48-7 1-(4-bromophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 
• 1267233-50-0 1-(4-methoxyphenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 
• 1266882-66-9 4-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonitrile 

Relevant articles and documents

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes utilizing S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate is an efficient approach to obtain a range of monofluorocyclopropane derivatives. So far, fluoromethylsulfonium salts have displayed the broadest scope for direct fluoromethylene transfer. In contrast to more commonly used fluorohalomethanes or freon derivatives, diarylfluoromethylsulfonium salts are bench stable, easy-to use reagents useful for the direct transfer of a fluoromethylene group to alkenes giving access to the challenging products-fluorocyclopropane derivatives. Interplay between the reactivity of the starting materials and stability of the fluorocyclopropanes formed determines the outcome of the process.

Vanadium-Catalyzed Condensation of Ethyl Cyanoacetate with Ketones

Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75–100% yield.

PIPERIDINE COMPOUNDS AS PCSK9 INHIBITORS

One aspect of the invention relates to a series of new PCSK9 inhibitor compounds comprising piperidine ring structures, including compounds of formula (I) and/or pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating PCSK9 receptor related diseases comprising administration of one or more compounds of formula (I) or a pharmaceutically acceptable salt thereof.