Description

(1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (CAS No. 911835-76-2) is a high-purity bicyclic amino acid derivative with the molecular formula C₈H₁₃NO₂. This compound features a rigid 3-azabicyclo[3.1.0]hexane scaffold with stereospecific (1R,2S,5S) configuration, making it a valuable chiral building block for pharmaceutical and medicinal chemistry research. The 6,6-dimethyl substitution enhances steric hindrance, while the carboxylic acid functionality allows for further derivatization. Supplied as a white to off-white solid, this product is rigorously characterized by ¹H NMR, ¹³C NMR, HPLC, and mass spectrometry to ensure ≥95% chemical purity. Ideal for use in peptidomimetics, enzyme inhibitor design, and asymmetric synthesis applications where constrained geometry is desired.

Properties

• CAS Number: 911835-76-2
• Complexity: 212
• IUPAC Name: (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• InChI: InChI=1S/C8H13NO2/c1-8(2)4-3-9-6(5(4)8)7(10)11/h4-6,9H,3H2,1-2H3,(H,10,11)/t4-,5-,6-/m0/s1
• InChI Key: SSKYNJZREFFALT-ZLUOBGJFSA-N
• Exact Mass: 155.094628657
• Molecular Formula: C8H13NO2
• Molecular Weight: 155.19
• SMILES: CC1([C@@H]2[C@H]1[C@H](NC2)C(=O)O)C
• Topological: 49.3
• Monoisotopic Mass: 155.094628657
• Synonyms: 911835-76-2, (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid, MQ8TV38FJH, (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo-[3.1.0]hexane-2-carboxylic acid, (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylicacid, (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo(3.1.0)hexane-2-carboxylic acid, 3-Azabicyclo(3.1.0)hexane-2-carboxylic acid, 6,6-dimethyl-, (1R,2S,5S)-, 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-dimethyl-, (1R,2S,5S)-, (1S,2S,5R)-6,6-dimethyl-3-azabicyclo, UNII-MQ8TV38FJH, SCHEMBL1592286, DTXSID00716730, AKOS016006487, AS-51668, DB-335845, CS-0053623, P13237, EN300-6764189, Q27451634

Application

This constrained bicyclic amino acid serves as a key intermediate in the synthesis of conformationally restricted peptides and peptidomimetics for drug discovery. The rigid scaffold is particularly useful for studying receptor-ligand interactions in neurological targets. Researchers employ this compound as a building block for protease inhibitors due to its ability to mimic transition states. The stereospecific configuration makes it valuable for asymmetric catalysis and chiral auxiliary applications.

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