4558-87-6

Basic information

• Product Name: 2,5-dimethylpiperidin-4-one
• Synonyms: 4-piperidinone, 2,5-dimethyl-
• CAS NO: 4558-87-6
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.1842
• Mol File: 4558-87-6.mol

Chemical Properties

• Boiling Point: 192.8°C at 760 mmHg
• Flash Point: 80.5°C
• Density: 0.915g/cm³
• Vapor Pressure: 0.48mmHg at 25°C
• Refractive Index: 1.43
• CAS DataBase Reference: 2,5-dimethylpiperidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-dimethylpiperidin-4-one(4558-87-6)
• EPA Substance Registry System: 2,5-dimethylpiperidin-4-one(4558-87-6)

Safety Data

• Hazardous Substances Data: 4558-87-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-dimethylpiperidin-4-one is used as a key building block for the synthesis of various drugs. Its unique structure allows for the development of new medicinal compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2,5-dimethylpiperidin-4-one serves as an essential intermediate in the production of agricultural chemicals. It contributes to the creation of innovative products designed to enhance crop protection and improve overall agricultural yields.
Used as a Chemical Intermediate:
2,5-dimethylpiperidin-4-one is utilized as an important intermediate in the synthesis of a wide range of compounds across various industries. Its versatility and reactivity make it a valuable component in the development of new chemical products.

Upstream product

• 13058-39-4 (E)-2-methylhexa-1,4-dien-3-one 
• 41854-15-3 1,5-dimethoxy-2-methyl-hexan-3-one 
• 93583-33-6 trans-1-α-Phenylethyl-2R,5S-dimethyl-4-piperidone 
• 93583-33-6 1-α-Phenylethyl-2S,5ξ-dimethyl-4-piperidone 
• 1252678-28-6 ethyl 3-{[3-ethoxy-2-methyl-3-oxopropyl]amino}butanoate 
• 220094-93-9 (1-methyl-2-ethoxycarbonylethyl)-(2-methyl-2-methoxycarbonylethyl)amine 

Downstream Products

• 39251-56-4 2r,5t-Dimethyl-4c-piperidinol 
• 39251-56-4 2r,5t-Dimethyl-4t-piperidinol 
• 39167-89-0 4-(3-buten-1-ynyl)-2,5-dimethylpiperidin-1-ol 
• 101496-66-6 2,5-dimethyl-1-(4-nitro-phenethyl)-piperidin-4-one 
• 109938-17-2 (2,5-dimethyl-4-oxo-piperidino)-phenyl-acetic acid methyl ester 
• 58476-13-4 2,5-dimethyl-4-oxo-piperidine-1-carboxylic acid ethyl ester 
• 101599-55-7 2,5-dimethyl-1-(3,4,5-trimethoxy-benzoyl)-piperidin-4-one 
• 63791-75-3 1-benzyl-2,5-dimethyl-piperidin-4-one 
• 107521-94-8 1-benzoyl-2,5-dimethyl-piperidin-4-one 
• 101939-13-3 2,5-dimethyl-1-(4-nitro-benzoyl)-piperidin-4-one 
• 102005-13-0 (+/-)-1-acetyl-2c,5c-dimethyl-4-phenyl-piperidin-4r-ol 
• 29280-78-2 1-(2-phenylethyl)-2,5-dimethyl-4-piperidone 
• 101105-60-6 2,5-dimethyl-4-oxo-piperidine-1-carboxylic acid benzyl ester 
• 102075-52-5 1-cinnamyl-2,5-dimethyl-piperidin-4-one 

Relevant articles and documents

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.

ASYMMETRIC SYNTHESIS AND ABSOLUTE CONFIGURATION OF 1-α-PHENYLETHYL-2,5-DIMETHYL-4-PIPERIDONE ISOMERS

Reaction of the methyl iodide of trans-1,2-5-trimethyl-4-piperidone with S-α-phenylethylamine proceeds asymmetrically and leads in 66percent optical yield to the formation of the cis- and trans-diastereomeric pair of 1-(α-phenylethyl)-2,5-dimethyl-4-piperidone, in which the new asymmetric centers possess the 2S,5S- and 2S,5R-configurations, respectively.According to x-ray structural analysis, the minor trans-1-(α-phenylethyl)-2,5-dimethyl-4-piperidone component possesses the 2R,5S-configuration.The occurrence of asymmetric synthesis accompanying transamination was confirmed via the preparation of enantiomers of trans-2,5- and trans-1,2,5-trimethyl-4-piperidones.