tert-Butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

Name: tert-Butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate
Brand: ChemScene
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CAS No. 325486-45-1
Cat. No. CS-0138540
Molecule weight197.23
Purity≥95%
MDL No.MFCD08437478

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tert-Butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate|CS-0138540

Structure of 325486-45-1

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General Information

CAS No. 325486-45-1
Cat. No. CS-0138540
Purity ≥95%
MDL No. MFCD08437478
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₅NO₃
Molecular Weight 197.23
Synonym(s) 4-Oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
SMILES O=C(N(CC1)C=CC1=O)OC(C)(C)C

Description

tert-Butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate features a reactive enolizable carbonyl adjacent to a dihydropyridine ring, enabling efficient functionalization in heterocyclic synthesis. This bench-stable, moisture-tolerant building block integrates readily into complex scaffolds via Michael additions and cycloadditions, offering a streamlined route to nitrogen-containing frameworks with high regiocontrol.

Application

tert-Butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate serves as a versatile building block for pyridine-based heterocycles, enabling efficient access to substituted dihydropyridines and pyridines via standard reduction, alkylation, and cyclization protocols. Its tert-butyl ester group provides excellent bench stability and facilitates straightforward purification, while the 4-oxo functionality offers predictable reactivity in nucleophilic additions and condensation reactions. This compound functions reliably in multistep synthesis workflows requiring controlled functional group interconversions.

Synthesis

Route1
- In-stock
  
  620-08-6
- In-stock
  
  24424-99-5
- ~41%
- In-stock
  
  325486-45-1
References
- Pizzuti, Maria Gabriella; Minnaard, Adriaan J.; Feringa, Ben L. Organic and Biomolecular Chemistry, 2008 , vol. 6, # 19 p. 3464 - 3466
Route2
- In-stock
  
  620-08-6
- In-stock
  
  865-47-4
- 1885-14-9
- ~%
- In-stock
  
  325486-45-1
References
- EP1204659 B1, ; Page/Page column 31 ;
Route3
- 79099-07-3
- ~70%
- In-stock
  
  325486-45-1
References
- Diao, Tianning; Stahl, Shannon S. Journal of the American Chemical Society, 2011 , vol. 133, # 37 p. 14566 - 14569

Safety Information

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GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H319-H411
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 46.61
LogP 1.71
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

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tert-Butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

CAS No. 325486-45-1

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