Cas no 76319-28-3 (rac-ethyl (1R,2R,5S)-3-azabicyclo3.1.0hexane-2-carboxylate)

Technical Introduction: rac-Ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate is a bicyclic compound featuring a rigid 3-azabicyclo[3.1.0]hexane scaffold with stereochemical complexity. The rac-ethyl ester derivative serves as a versatile intermediate in organic synthesis, particularly for the development of pharmacologically active molecules. Its strained bicyclic structure and functionalized carboxylate group enable selective modifications, making it valuable for medicinal chemistry applications, such as the synthesis of chiral ligands or constrained peptidomimetics. The compound’s stereochemistry (1R,2R,5S) may offer distinct reactivity or binding properties in asymmetric synthesis. High purity and well-defined stereochemistry ensure reproducibility in research and industrial applications. Suitable for use under controlled conditions, it requires handling in accordance with standard laboratory safety protocols.
rac-ethyl (1R,2R,5S)-3-azabicyclo3.1.0hexane-2-carboxylate structure
76319-28-3 structure
Product Name:rac-ethyl (1R,2R,5S)-3-azabicyclo3.1.0hexane-2-carboxylate
CAS No:76319-28-3
MF:C8H13NO2
MW:155.194322347641
CID:561230
PubChem ID:13150529
Update Time:2025-05-24

rac-ethyl (1R,2R,5S)-3-azabicyclo3.1.0hexane-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid, ethyl ester, [1R-(1a,2a,5a)]- (9CI)
    • 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,ethylester,[1R-(1-alpha-,2-alpha-,5-alpha-)]-(9CI)
    • 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,ethylester,[1R-(1-α-,2-α-,5-α-)]-(9CI)
    • rac-ethyl (1R,2R,5S)-3-azabicyclo3.1.0hexane-2-carboxylate
    • EN300-27731784
    • rac-ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate
    • 72496-48-1
    • 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,ethylester,(1-alpha-,2-alpha-,5-alpha-)-(9ci)
    • 76319-28-3
    • Inchi: 1S/C8H13NO2/c1-2-11-8(10)7-6-3-5(6)4-9-7/h5-7,9H,2-4H2,1H3/t5-,6-,7-/m1/s1
    • InChI Key: QJFZMDWMBRUEMA-FSDSQADBSA-N
    • SMILES: O(CC)C([C@H]1[C@@H]2C[C@@H]2CN1)=O

Computed Properties

  • Exact Mass: 155.09500
  • Monoisotopic Mass: 155.094628657g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 3
  • Complexity: 181
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.5
  • Topological Polar Surface Area: 38.3?2

Experimental Properties

  • PSA: 38.33000
  • LogP: 0.48620

rac-ethyl (1R,2R,5S)-3-azabicyclo3.1.0hexane-2-carboxylate Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Enamine
EN300-27731784-1g
rac-ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate
76319-28-3
1g
$0.0 2023-09-10
Enamine
EN300-27731784-1.0g
rac-ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate
76319-28-3 95.0%
1.0g
$0.0 2025-03-19

Additional information on rac-ethyl (1R,2R,5S)-3-azabicyclo3.1.0hexane-2-carboxylate

Rac-Ethyl (1R,2R,5S)-3-Azabicyclo[3.1.0]Hexane-2-Carboxylate: A Comprehensive Overview

The compound rac-ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate (CAS No. 76319-28-3) is a unique bicyclic compound with significant potential in various chemical and pharmaceutical applications. This compound belongs to the class of bicyclic amines and is characterized by its rigid bicyclic structure, which plays a crucial role in its biological activity and chemical reactivity.

The bicyclic structure of this compound is a key feature that contributes to its stability and selectivity in various reactions. The azabicyclo[3.1.0]hexane framework is a six-membered ring system with one nitrogen atom, creating a rigid and strained environment that enhances its reactivity in certain chemical transformations. Recent studies have shown that such bicyclic systems are highly valuable in the design of novel bioactive molecules due to their ability to mimic natural product frameworks.

One of the most notable aspects of rac-ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate is its stereochemistry. The compound exists as a racemic mixture, meaning it contains equal amounts of the two enantiomers: (1R,2R,5S) and (1S,2S,5R). This stereochemical property is critical in pharmaceutical applications, where the stereochemistry of a molecule can significantly influence its pharmacokinetics and efficacy.

Recent advancements in synthetic chemistry have enabled the efficient synthesis of this compound through various methodologies. For instance, researchers have employed ring-closing metathesis and stereoselective alkylation techniques to construct the azabicyclo framework with high precision. These methods not only enhance the yield but also allow for better control over the stereochemistry of the final product.

In terms of applications, rac-ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate has shown promise in drug discovery programs targeting various therapeutic areas. Its rigid structure makes it an ideal candidate for designing molecules with high binding affinity to specific biological targets such as enzymes and receptors.

Moreover, this compound has been extensively studied for its potential as a building block in medicinal chemistry. Its ability to undergo various functional group transformations makes it versatile for constructing complex molecular architectures. For example, researchers have utilized this compound as a starting material for synthesizing bioactive agents with potential anti-inflammatory and anticancer properties.

The carboxylate group present in this compound adds another layer of functionality by enabling further modifications such as esterification or amidation. These modifications can significantly alter the physicochemical properties of the molecule, making it suitable for different biological assays and pharmacological evaluations.

In conclusion, rac-ethyl (1R,2R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylate is a versatile and intriguing compound with a wide range of applications in organic synthesis and drug discovery. Its unique bicyclic structure, stereochemical properties, and functional versatility make it an invaluable tool for researchers in the field of chemical biology.

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