Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate

Name: Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate
Brand: ChemScene
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CAS No. 135908-33-7
Cat. No. CS-0032321
Purity≥95%
MDL No.MFCD20693756

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Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate|CS-0032321

Structure of 135908-33-7

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General Information

CAS No. 135908-33-7
Cat. No. CS-0032321
Purity ≥95%
MDL No. MFCD20693756
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₇NO₂
Molecular Weight 183.25
Synonym(s) Bicyclo[2.2.2]octane-1-carboxylic acid, 4-amino-, methyl ester
SMILES O=C(OC)C12CCC(CC2)(N)CC1

Description

Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate features a rigid bicyclic scaffold that enforces conformational restraint, enhancing target selectivity in medicinal chemistry applications. The pendant amino group enables facile derivatization, while the ester functionality supports downstream transformations. This bench-stable compound integrates readily into complex molecular architectures.

Application

Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate serves as a versatile scaffold for medicinal chemistry and asymmetric synthesis, offering a rigid, three-dimensional core with orthogonal functional handles. The pendant amine enables facile derivatization via acylation, alkylation, or reductive amination, while the ester group supports hydrolysis to the carboxylic acid or conversion to other carbonyl derivatives. Its bench-stable nature and compatibility with standard reaction conditions make it a practical building block for constructing complex heterocycles and bioactive molecules in drug discovery campaigns.

Synthesis

Route1
- 862501-91-5
- ~10%
- In-stock
  
  135908-33-7
References
- Yeh, Vince S.C.; Kurukulasuriya, Ravi; Madar, David; Patel, Jyoti R.; Fung, Steven; Monzon, Katina; Chiou, William; Wang, Jiahong; Jacobson, Peer; Sham, Hing L.; Link Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 20 p. 5408 - 5413
Route2
- In-stock
  
  18720-35-9
- ~%
- In-stock
  
  135908-33-7
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 20 p. 5408 - 5413

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 52.32
LogP 1.2111
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Bridge Rings compounds Quinine Ring compounds

Key Words

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Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate

CAS No. 135908-33-7

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