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Methyl 2-acetamidoacrylate
Methyl 2-acetamidoacrylate is the organic compound with the formula CH2=C(NHC(O)CH3)CO2CH3. It is the methyl ester of an ''N''-acetylacrylic acid, which in turn is a derivative of the unstable compound dehydroalanine. Acetylation of the amine in the latter compound prevents tautomerization. It is a white solid. The compound can be prepared from methyl 2-acetamidopropionate (CH3CH(NHC(O)CH3)CO2CH3), i.e. the methyl ester of N-acetylalanine. Methyl 2-acetamidoacrylate undergoes Michael reaction In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a c ...s, e.g. by thiolates. References {{Reflist Acetamides Methyl esters ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ...
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Methyl Ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to the aroma of fruits, butter, cheese, vegetables like celery and other foods. Esters can be formed from oxoacids (e.g. esters of acetic acid, carbonic acid, sulfuric acid ...
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Acetyl
In organic chemistry, an acetyl group is a functional group denoted by the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl group is called an ethanoyl group. An acetyl group contains a methyl group () that is single-bonded to a carbonyl (), making it an acyl group. The carbonyl center of an acyl radical has one non-bonded electron with which it forms a chemical bond to the remainder (denoted with the letter ''R'') of the molecule. The acetyl moiety is a component of many organic compounds, including acetic acid, the neurotransmitter acetylcholine, acetyl-CoA, acetylcysteine, acetaminophen (also known as paracetamol), and acetylsalicylic acid (also known as aspirin). Acetylation Acetylation is the chemical reaction known as "ethanoylation" in the IUPAC nomenclature. It depicts a reactionary process that injects an acetyl functional group into a chemical ...
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Acrylic Acid
Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually. History The word "acrylic" was coined in 1843, for a chemical derivative of acrolein, an acrid-smelling oil derived from glycerol. Production Acrylic acid is produced by oxidation of propylene, which is a byproduct of the production of ethylene and gasoline: : Historical methods Because acrylic acid and its esters have long been valued commercially, many other methods have been developed. Most have been abandoned for economic or environmental reasons. An early method was the hydrocarboxylation of acetylene (" Reppe chemistry"): : This method requires nickel carbonyl, high pressures of ...
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Dehydroalanine
Dehydroalanine (Cα,β-didehydroalanine, α,β-di-dehydroalanine, 2-aminoacrylate, or 2,3-didehydroalanine) is a dehydroamino acid. It does not exist in its free form, but it occurs naturally as a residue found in peptides of microbial origin. As an amino acid residue, it is unusual because it has an unsaturated backbone. Structure and reactivity Like most primary enamines, dehydroalanine is unstable. Dehydroalanine hydrolyzes to pyruvate. ''N''-Acylated derivatives of dehydroalanine, such as peptides and related compounds, are stable. For example, methyl 2-acetamidoacrylate is the N-acetylated derivative of the ester. As a residue in a peptide, it is generated by a post translational modification. The required precursors are serine or cysteine residues, which undergo enzyme-mediated loss of water and hydrogen sulfide, respectively. Most amino acid residues are unreactive toward nucleophiles, but those containing dehydroalanine or some other dehydroamino acids are exception ...
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Acetylation
: In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed ''acetate esters'' or simply ''acetates''. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound. Acetylation/deacetylation in biology Histone deacetylases "play crucial roles in gene transcription and most likely in all eukaryotic biological processes that involve chromatin". Acetylation is one type of post-translational modification of proteins. The acetylation of the ε-amino group of lysine, which is common, converts a charged side chain to a neutral one. Acetylation/deacetylation of histones also plays a role in gene expression and cancer. These modifications are effected by enzymes called histone acetyltransferases (HATs) and histone deacetylases (HDACs). Two general mechanisms are known for deacetylation. One mechanism involves zinc binding to the acetyl o ...
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Amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ...
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Michael Reaction
In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon–carbon bonds. The Michael addition is an important atom-economical method for diastereoselective and enantioselective C–C bond formation, and many asymmetric variants exist : In this general Michael addition scheme, either or both of R and R' on the nucleophile (the Michael donor) represent electron-withdrawing substituents such as acyl, cyano, nitro, or sulfone groups, which make the adjacent methylene hydrogen acidic enough to form a carbanion when reacted with the base, ''B:''. For the alkene (the Michael acceptor), the R" substituent is usually a carbonyl, which makes the co ...
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Acetamides
Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is an amide derived from ammonia and acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound ''N'',''N''-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral with the IMA symbol: Ace. Production Laboratory scale Acetamide can be produced in the laboratory from ammonium acetate by dehydration: : H4CH3CO2] → CH3C(O)NH2 + H2O Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination. It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, u ...
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