121507-66-2

Basic information

• Product Name: phenyl 4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate
• Synonyms: phenyl 4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate
• CAS NO: 121507-66-2
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22064
• Mol File: 121507-66-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: phenyl 4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate(121507-66-2)
• EPA Substance Registry System: phenyl 4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate(121507-66-2)

Safety Data

• Hazardous Substances Data: 121507-66-2(Hazardous Substances Data)

Upstream product

• 620-08-6 4-methoxypyridine 
• 1885-14-9 phenyl chloroformate 
• 24681-60-5 1,2,3,4-tetrahydro-4-oxopyridine 

Downstream Products

• 325486-45-1 tert-butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate 
• 1609582-79-7 phenyl 5-(2-ethoxy-1,1-difluoro-2-oxoethyl)-4-oxo-2,3-dihydropyridine-1-carboxylate 
• 121507-73-1 2-(3-ethoxycarbonylpropyl)-1-phenoxycarbonyl-1,2,5,6-tetrahydropyridine 
• 121507-72-0 2-(2-ethoxycarbonylethyl)-1-phenoxycarbonyl-1,2,5,6-tetrahydropyridine 
• 121507-71-9 2-(4-chlorobutyl)-1-phenoxycarbonyl-1,2,5,6-tetrahydropyridine 
• 121507-70-8 2-n-butyl-1-phenoxycarbonyl-1,2,5,6-tetrahydropyridine 
• 121507-68-4 4-methoxy-1-phenoxycarbonyl-1,2,3,4-tetrahydropyridine 
• 121507-69-5 2-methyl-1-phenoxycarbonyl-1,2,5,6-tetrahydropyridine 
• 121507-67-3 4-hydroxy-1-phenoxycarbonyl-1,2,3,4-tetrahydropyridine 

Relevant articles and documents

Catalytic enantioselective conjugate addition of dialkylzinc reagents to N-substituted-2,3-dehydro-4-piperidones

The first, highly enantioselective, copper/phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents to N-substituted 2,3-dehydro-4- piperidones is described. The Royal Society of Chemistry 2005.

New oxidative demetalation protocol for molybdenum π-complexes: Enantiocontrolled synthesis of unsaturated ketones and lactones

An efficient and general oxidative demetalation of (η3-allyl)molybdenum complexes using pyridinium dichromate allows the introduction of a carbonyl group at an allylic terminus of the π-system. The process takes place with high regiocontrol and can lead to the preparation of unsaturated ketones and lactones of high enantiopurity.

Design, Synthesis, and Pharmacological Characterization of a Neutral, Non-Prodrug Thrombin Inhibitor with Good Oral Pharmacokinetics

Despite extensive research on small molecule thrombin inhibitors for oral application in the past decades, only a single double prodrug with very modest oral bioavailability has reached human therapy as a marketed drug. We have undertaken major efforts to identify neutral, non-prodrug inhibitors. Using a holistic analysis of all available internal data, we were able to build computational models and apply these for the selection of a lead series with the highest possibility of achieving oral bioavailability. In our design, we relied on protein structure knowledge to address potency and identified a small window of favorable physicochemical properties to balance absorption and metabolic stability. Protein structure information on the pregnane X receptor helped in overcoming a persistent cytochrome P450 3A4 induction problem. The selected compound series was optimized to a highly potent, neutral, non-prodrug thrombin inhibitor by designing, synthesizing, and testing derivatives. The resulting optimized compound, BAY1217224, has reached first clinical trials, which have confirmed the desired pharmacokinetic properties.

REGIO- AND STEREOSELECTIVE ADDITION OF NUCLEOPHILES TO 1-PHENOXYCARBONYL-2,3-DIHYDROPYRIDINIUM SALTS

Several 2-alkyl-1-phenoxycarbonyl-Δ3-piperidines were prepared by the addition of alkylzinc iodides to dihydropyridinium salt (9).The treatment of 4-hydroxy-2-methyl-1-phenoxycarbonyl-1,2,3,4-tetrahydropyridine (12) with allyltrimethylsilane in the presence of a variety of Lewis acids was studied and found to give cis- and trans-2,6-dialkyl-Δ3-piperidines (14) and (15) in moderate to good yield.Among the Lewis acids studied, stannyl chloride gave the best yield with good stereoselectivity (84:16) favoring the cis-isomer (14).The analogous reaction of the 4-metho xy derivative (13) with organozinc reagents was examined and found to give the cis-isomers (17) as the major products.Using this metodology, the cis-piperidine alkaloid (+/-)-dihydropinidine, was prepared in six steps from 4-methoxypyridine.

THE ADDITION OF ALKYLZINC IODIDES TO 1-(PHENOXYCARBONYL)-2,3-DIHYDROPYRIDINIUM SALTS. A SYNTHESIS OF 2-ALKYL-Δ3-PIPERIDINES.

Several 2-alkyl-1-(phenoxycarbonyl)-Δ3-piperidines were prepared by the addition of alkylzinc iodides to 1-(phenoxycarbonyl)-2,3-dihydropyridinium salts.