Cas no 1648868-97-6 (tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate)

Technical Introduction: tert-Butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate is a chiral bicyclic compound featuring a rigid 3-azabicyclo[3.1.0]hexane scaffold with a tert-butyl carboxylate protecting group and a 2-hydroxyethyl substituent. The stereochemistry (1R,5S,6s) ensures precise spatial orientation, making it valuable for asymmetric synthesis and medicinal chemistry applications. The tert-butyl ester enhances stability and facilitates selective deprotection under mild conditions. The hydroxyethyl side chain offers functional versatility for further derivatization. This compound is particularly useful as an intermediate in the synthesis of pharmacologically active molecules, leveraging its constrained ring system to influence conformational properties and binding affinity. High purity and well-defined stereochemistry ensure reproducibility in research and development.
tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate structure
1648868-97-6 structure
Product Name:tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
CAS No:1648868-97-6
MF:C12H21NO3
MW:227.300043821335
MDL:MFCD20231349
CID:4610556
PubChem ID:117833564
Update Time:2025-05-22

tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate Chemical and Physical Properties

Names and Identifiers

    • (Meso-1R,5S,6S)-Tert-Butyl 6-(2-Hydroxyethyl)-3-Azabicyclo[3.1.0]Hexane-3-Carboxylate
    • (1R,5S,6S)-tert-butyl 6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • tert-Butyl (1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • (meso-1R,5S,6S)-t-Butyl 6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • AKOS027430025
    • CS-0048099
    • W14362
    • 1648868-97-6
    • 1330765-43-9
    • SCHEMBL16415112
    • AS-74103
    • SCHEMBL16415113
    • rel-(1R,5S,6r)-tert-Butyl 6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • tert-butyl (1R,5S)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • YQC86897
    • (1R,5S,6S)-tert-butyl6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • tert-butyl exo-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
    • exo-3-Boc-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane
    • MFCD20231349
    • P18011
    • MDL: MFCD20231349
    • Inchi: 1S/C12H21NO3/c1-12(2,3)16-11(15)13-6-9-8(4-5-14)10(9)7-13/h8-10,14H,4-7H2,1-3H3/t8?,9-,10+
    • InChI Key: SSIJALKTEBLKKA-PBINXNQUSA-N
    • SMILES: O(C(C)(C)C)C(N1C[C@H]2C(CCO)[C@H]2C1)=O

Computed Properties

  • Exact Mass: 227.15214353 g/mol
  • Monoisotopic Mass: 227.15214353 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 273
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.1
  • Topological Polar Surface Area: 49.8
  • Molecular Weight: 227.30

tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate Pricemore >>

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Additional information on tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate: A Comprehensive Overview

The compound with CAS No. 1648868-97-6, known as tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate, is a highly specialized organic compound that has garnered significant attention in the fields of organic chemistry and pharmacology. This compound is notable for its complex bicyclic structure and its potential applications in drug design and synthesis.

tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate belongs to the class of bicyclic compounds, which are characterized by their two fused ring systems. The bicyclo[3.1.0]hexane framework is a unique structural motif that provides this compound with exceptional stability and bioactivity potential. The presence of the tert-butyl group and the 2-hydroxyethyl substituent further enhances its chemical properties, making it a valuable intermediate in various synthetic pathways.

Recent studies have highlighted the importance of bicyclic compounds in medicinal chemistry due to their ability to mimic natural product scaffolds and exhibit potent biological activities. For instance, researchers have demonstrated that tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate can serve as a versatile building block for constructing bioactive molecules with anti-inflammatory and antioxidant properties.

The synthesis of this compound involves a multi-step process that combines advanced organic chemistry techniques such as ring-closing metathesis and stereocontrolled reactions. The stereochemistry of the compound is critical, as it determines the biological activity and pharmacokinetic properties of the molecule. The rel-(1R,5S,6s) configuration ensures optimal interactions with biological targets, making this compound a promising candidate for drug development.

In terms of applications, tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate has been explored in the context of enzyme inhibition and receptor binding studies. Its ability to modulate key cellular pathways has been validated through in vitro assays, where it demonstrated remarkable selectivity and potency against various targets.

From an environmental perspective, the synthesis and handling of this compound adhere to green chemistry principles, minimizing waste generation and promoting sustainability in chemical processes. Its stability under standard storage conditions also makes it suitable for large-scale production and distribution.

In conclusion, tert-butyl rel-(1R,5S,6s)-6-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate represents a cutting-edge advancement in organic synthesis with broad implications for drug discovery and development.

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