Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Name: Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 66207-08-7
Cat. No. CS-W004203
Purity≥95%
MDL No.MFCD12407051

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Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate|CS-W004203

Structure of 66207-08-7

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General Information

CAS No. 66207-08-7
Cat. No. CS-W004203
Purity ≥95%
MDL No. MFCD12407051
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₅NO₃
Molecular Weight 233.26
Synonym(s) 7-Oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic Acid Benzyl Ester
SMILES O=C(OCC1=CC=CC=C1)N2CCC(O3)C3C2

Description

Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate features a rigid, oxygen- and nitrogen-containing bicyclic core that imparts conformational restraint. This structural motif enhances target selectivity in medicinal chemistry applications. The benzyl ester group enables straightforward deprotection under mild conditions, facilitating downstream functionalization. The compound exhibits excellent stability and solubility in common organic solvents.

Application

Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate serves as a versatile bicyclic scaffold for medicinal chemistry and synthetic methodology development. The constrained 3-azabicyclo[4.1.0]heptane core offers defined stereochemistry and enhanced metabolic stability, while the benzyl ester enables straightforward deprotection under standard conditions. It functions as a key building block in the synthesis of bioactive heterocycles and supports diverse transformations including nucleophilic ring-opening and transition-metal-catalyzed coupling reactions.

Synthesis

Route1
- In-stock
  
  66207-23-6
- ~99%
- In-stock
  
  66207-08-7
References
- Newhouse, Bradley J.; Hansen, Joshua D.; Grina, Jonas; Welch, Mike; Topalov, George; Littman, Nicole; Callejo, Michele; Martinson, Matthew; Galbraith, Sarah; Laird, Ellen R.; Brandhuber, Barbara J.; Vigers, Guy; Morales, Tony; Woessner, Rich; Randolph, Nikole; Lyssikatos, Joseph; Olivero, Alan Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3488 - 3492
Route2
- 174681-58-4
- 937-14-4
- ~97%
- In-stock
  
  66207-08-7
References
- ARRAY BIOPHARMA INC. Patent: WO2009/140320 A1, 2009 ; Location in patent: Page/Page column 78 ; WO 2009/140320 A1
Route3
- 694-05-3
- ~%
- In-stock
  
  66207-08-7
References
- Epple, Robert; Urbina, Hugo D.; Russo, Ross; Liu, Hong; Mason, Daniel; Bursulaya, Badry; Tumanut, Christine; Li, Jun; Harris, Jennifer L. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 5 p. 1254 - 1259

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 42.07
LogP 1.7963
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Oxane compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

CAS No. 66207-08-7

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