17097-90-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 26, 1946 DOI: 10.1021/ja01205a008Synthetic Communications, 21, p. 1071, 1991 DOI: 10.1080/00397919108019796

Upstream product

• 83-13-6 diethyl 2-phenylmalonate 
• 124-38-9 carbon dioxide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 2613-89-0 phenylmalonic acid 
• 15231-78-4 2.2-dimethyl-5-phenyl-1,3-dioxane-4,6-dione 
• 541-41-3 chloroformic acid ethyl ester 
• 103-82-2 phenylacetic acid 

Downstream Products

• 5413-05-8 ethyl 2-phenylacetoacetate 
• 39638-64-7 6β-((Ξ)-2-ethoxycarbonyl-2-phenyl-acetylamino)-penicillanic acid 
• 141869-55-8 ethyl α,α-bis(methylthio)phenylacetate 
• 60764-00-3 α-deuterio(phenyl)acetic acid 
• 101-97-3 Ethyl 2-phenylethanoate 
• 1026544-39-7 C₂₈H₄₄N₄O₇ 
• 54095-15-7 2-ethyl-2-phenylmalonyldichloride 
• 1056476-57-3 ethyl 3-(1,3-di(p-tolyl)ureido)-3-oxo-2-phenylpropanoate 
• 119-43-7 ethyl 2-phenylbutanoate 
• 1056476-61-9 ethyl 3-(1,3-diisopropylureido)-3-oxo-2-phenylpropanoate 
• 1246373-61-4 (2R,4S,5R)-2-(tert-butyl)-3-((R)-3-ethoxy-2-phenyl-3-oxopropanoyl)-4-methoxycarbonyl-5-methyloxazolidine 
• 1246373-60-3 (2R,4S,5R)-2-(tert-butyl)-3-((S)-3-ethoxy-2-phenyl-3-oxopropanoyl)-4-methoxycarbonyl-5-methyloxazolidine 
• 1277102-48-3 phenylmalonic acid diphenylmethyl tert-butyl ester 

Relevant academic research and scientific papers

Three-component, one-pot sequential synthesis of N-Aryl, N′-alkyl barbiturates

(Chemical Equation Presented) Condensation between N-alkyl, N′-aryl carbodiimides and malonic acid monoesters leads to a high-yield formation of N-acyl urea derivatives that could be cyclized to C-monosubstituted barbiturates by addition of a suitable bas

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides

Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.

Double decarboxylative route to 3-substituted pyrrolidines: Reaction of monoalkyl malonates and related carboxylic acids with sarcosine and formaldehyde

Three-component reactions of monoalkyl malonates, cyanoacetic acids or 2-ketocarboxylic acids, N-methylglycine, and formaldehyde were developed to rapidly access 3-substituted pyrrolidines in 17–97% yield. These reactions represent a double decarboxylative domino-sequence promoted by pyrrolidine and involve N-methylazomethine ylide as the reactive intermediate.

Synthetic access to 3,4-disubstituted pyroglutamates from tetramate derivatives from serine, allo-threonine and cysteine

A route allowing the conversion of substituted tetramates to 3,4-disubstituted pyroglutamates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is both general and fully stereoselective.

Synthetic method of tropicamide

The invention relates to a production method of chemical medicines and particularly relates to a synthetic method of tropicamide. The synthetic method comprises the steps of carrying out hydrolysis and acylation on the raw material, namely diethyl phenylmalonate, condensing diethyl phenylmalonate with N-ethyl-4-methylpyridine amine, and generating reduction reaction with hydroboron, so as to obtain tropicamide. The synthetic method has the beneficial effects that the raw material cost is low, the properties of an intermediate product are stable, impurities are few, the operation steps such aspurification are reduced, and the process is simplified; reaction conditions are safe and mild, extremely toxic substances are not introduced, and the industrial amplified production is promoted; andby optimizing the raw material ratio, the total yield of the reaction is increased to be 65% and is greatly increased, and the production cost is lowered.

Novel arylalkenylpropargylamines as neuroprotective, potent, and selective monoamine oxidase B inhibitors for the treatment of Parkinson's disease

To develop novel neuroprotective agents, a library of novel arylalkenylpropargylamines was synthesized and tested for inhibitory activities against monoamine oxidases. From this, a number of highly potent and selective monoamine oxidase B inhibitors were identified. Selected compounds were also tested for neuroprotection in in vitro studies with PC-12 cells treated with 6-OHDA and rotenone, respectively. It was observed that some of the compounds tested yielded a marked increase in survival in PC-12 cells treated with the neurotoxins. This indicates that these propargylamines are able to confer protection against the effects of the toxins and may also be considered as novel disease-modifying anti-Parkinsonian agents, which are much needed for the therapy of Parkinson's disease.

NEW ARYLALKENYLPROPARGYLAMINE DERIVATIVES EXHIBITING NEUROPROTECTIVE ACTION FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

The invention relates to novel arylalkenylpropargylamine derivatives of general formula (I) or enantiomers or diastereomers thereof or salts, optionally pharmaceutically acceptable salts, or solvates of any of these. The compounds can be used in treating or preventing a disease or condition in a mammal related to monoamine oxidase dysfunction, especially in neurodegenerative diseases, e.g. Parkinson's disease, Alzheimer's disease or Huntington's disease.

Substrate specificity of an esterase from the archaeon Sulfolobus tokodaii bearing a GGG(A)X motif

A GGG(A)X-type esterase (Est0071) from an archaeon catalyzes asymmetric hydrolysis of prochiral bulky malonic diesters in good enantioselectivity. The selectivity of Est0071 was for the opposite enantiomer to that previously shown for pig liver esterase, and the resulting enantiomeric excess of the products was higher. Est0071 could also catalyze the hydrolysis of various acetates of secondary alcohols, and showed moderate enantioselectivity in these reactions.

Neutral nazarov-type cyclization catalyzed by palladium(0)

Joining the circle: The first Pd0 catalyzed Nazarov-type cyclization of diketoesters (see scheme) proceeds in 70 % to 95 % yield under strictly neutral pH conditions. Aryl substitution of the diketoesters is not required, so the reaction shows great versatility and can also proceed with aliphatic substrates. Copyright