Benzyl 5-oxo-2aza-bicyclo[2.2.1]heptance-2-carboxylate

Name: Benzyl 5-oxo-2aza-bicyclo[2.2.1]heptance-2-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 140927-13-5
Cat. No. CS-0060539
Purity≥97%
MDL No.None

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Benzyl 5-oxo-2aza-bicyclo[2.2.1]heptance-2-carboxylate|CS-0060539

Structure of 140927-13-5

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General Information

CAS No. 140927-13-5
Cat. No. CS-0060539
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₅NO₃
Molecular Weight 245.27
Synonym(s) Benzyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate
SMILES C1=CC=C(C=C1)COC(=O)N2CC3CC2CC3=O

Description

Benzyl 5-oxo-2aza-bicyclo[2.2.1]heptane-2-carboxylate is a strained, electron-deficient bicyclic scaffold featuring a ketone at C5 and a benzyl ester at C2. This configuration enables direct functionalization at the bridgehead position, facilitating efficient access to complex nitrogen-containing heterocycles in synthetic and medicinal chemistry workflows.

Application

Benzyl 5-oxo-2aza-bicyclo[2.2.1]heptane-2-carboxylate serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to nitrogen-containing bicyclic frameworks. Its cyclohexenone-like reactivity facilitates Michael additions, Diels–Alder reactions, and functional group interconversions under standard conditions. The benzyl ester provides convenient handling and orthogonal cleavage, while the enone moiety offers high regioselectivity in nucleophilic transformations. This compound functions as a key building block for medicinal chemistry campaigns involving constrained scaffolds.

Synthesis

Route1
- 140927-12-4
- ~60%
- In-stock
  
  140927-13-5
References
- Carroll, F. Ivy; Abraham, Phillip; Chemburkar, Sanjay; He, Xu-Chang; Mascarella, S. Wayne; et al. Journal of Medicinal Chemistry, 1992 , vol. 35, # 12 p. 2184 - 2191
Route2
- 6671-85-8
- ~%
- In-stock
  
  140927-13-5
References
- Journal of Medicinal Chemistry, , vol. 35, # 12 p. 2184 - 2191
Route3
- 542-92-7
- ~%
- In-stock
  
  140927-13-5
References
- Journal of Medicinal Chemistry, , vol. 35, # 12 p. 2184 - 2191

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 46.61
LogP 1.9865
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ketone

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Benzyl 5-oxo-2aza-bicyclo[2.2.1]heptance-2-carboxylate

CAS No. 140927-13-5

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