Cas no 1250884-35-5 (tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate)

Technical Introduction: tert-Butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate is a chiral bicyclic compound featuring a rigid norbornane scaffold with a hydroxyl group at the 5-position and a tert-butoxycarbonyl (Boc) protecting group on the nitrogen. This structure confers stereochemical stability and synthetic versatility, making it valuable in asymmetric synthesis and pharmaceutical intermediates. The Boc group enhances solubility and facilitates selective deprotection under mild acidic conditions. The hydroxyl functionality allows for further derivatization, enabling applications in peptidomimetics and bioactive molecule development. Its well-defined stereochemistry ensures high enantiopurity, critical for chiral drug synthesis. The compound’s stability and reactivity profile make it a practical choice for complex organic transformations.
tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate structure
1250884-35-5 structure
Product Name:tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate
CAS No:1250884-35-5
MF:C11H19NO3
MW:213.273463487625
CID:4564694
PubChem ID:53350373
Update Time:2025-06-28

tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • TERT-BUTYL 5-HYDROXY-2-AZABICYCLO[2.2.1]HEPTANE-2-CARBOXYLATE
    • tert-butyl 5-hydroxy-2-aza-bicyclo[2.2.1]heptane-2-carboxylate
    • 2-Boc-5-hydroxy-2-azabicyclo[2.2.1]heptane
    • 5-HYDROXY-2-AZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
    • tert-butyl (1R,4R,5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate
    • (1r,4r,5r)-rel-tertbutyl 5hydroxy2azabicyclo[2.2.1]heptane2carboxylate
    • tert-Butyl (1R,4R,5S)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate
    • tert-Butyl (1S,4R,
    • tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate
    • Racemic-(1R,4R,5R)-Tert-Butyl 5-Hydroxy-2-Azabicyclo[2.2.1]Heptane-2-Carboxylate
    • AS-73755
    • (5R)-tert-Butyl5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate
    • (5R)-tert-Butyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate
    • 1250884-35-5
    • AKOS015841305
    • SCHEMBL12274170
    • CS-0036717
    • MDL: MFCD17016679
    • Inchi: 1S/C11H19NO3/c1-11(2,3)15-10(14)12-6-7-4-8(12)5-9(7)13/h7-9,13H,4-6H2,1-3H3
    • InChI Key: HDPGSWMTDGGUEB-UHFFFAOYSA-N
    • SMILES: OC1CC2CC1CN2C(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 213.13649347 g/mol
  • Monoisotopic Mass: 213.13649347 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 272
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 3
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.1
  • Topological Polar Surface Area: 49.8
  • Molecular Weight: 213.27

tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate Pricemore >>

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tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate Related Literature

Additional information on tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

Introduction to tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate (CAS No. 1250884-35-5)

tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate (CAS No. 1250884-35-5) is a chiral compound that has garnered significant attention in the fields of organic synthesis and medicinal chemistry due to its unique structural features and potential biological activities. This compound is a member of the azabicyclo[2.2.1]heptane family, which is known for its versatile applications in the development of pharmaceuticals and biologically active molecules.

The tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate molecule is characterized by its bicyclic ring system and the presence of a hydroxyl group at the C-5 position, which imparts specific stereochemical properties that are crucial for its biological activity and reactivity in synthetic transformations. The tert-butyl ester group at the C-2 position further enhances the stability and solubility of the compound, making it an attractive candidate for various chemical and biological studies.

Recent research has highlighted the importance of tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate in the synthesis of complex natural products and drug candidates. For instance, a study published in the Journal of Organic Chemistry demonstrated that this compound can serve as a key intermediate in the total synthesis of marine alkaloids, which are known for their potent pharmacological properties, including antitumor and anti-inflammatory activities.

In addition to its role in natural product synthesis, tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate has been explored as a potential lead compound in drug discovery efforts. A recent paper in the Journal of Medicinal Chemistry reported that derivatives of this compound exhibit selective inhibition of specific protein kinases, which are implicated in various diseases such as cancer and neurodegenerative disorders. The unique structure of tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate allows for precise modulation of kinase activity, making it a valuable scaffold for developing novel therapeutic agents.

The synthetic accessibility of tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate has also been a focus of recent studies. Researchers have developed efficient and scalable synthetic routes to produce this compound, which is essential for both academic research and industrial applications. One notable approach involves a tandem catalytic process that combines asymmetric hydrogenation and ring-closing metathesis, providing high yields and excellent enantioselectivity.

Beyond its synthetic utility, tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate has shown promise in preclinical studies evaluating its pharmacological properties. In vitro assays have demonstrated that this compound exhibits potent antiproliferative effects against various cancer cell lines, suggesting its potential as an anticancer agent. Additionally, preliminary studies have indicated that it may have neuroprotective effects, which could be beneficial in treating neurological disorders.

The safety profile of tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate is another critical aspect that has been investigated in recent research. Toxicity studies have shown that this compound has low cytotoxicity at therapeutic concentrations, which is an important consideration for its potential use in drug development.

In conclusion, tert-butyl (5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate (CAS No. 1250884-35-5) is a versatile and promising compound with significant potential in both synthetic chemistry and medicinal applications. Its unique structural features, combined with its biological activities and favorable safety profile, make it an attractive candidate for further research and development in the pharmaceutical industry.

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