ethyl (1S,2R)-1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropane-1-carboxylate
$365.00
CAS No.: 924307-75-5
Catalog No.: 195948
Purity: 95%
MF: C13H21NO4
MW: 255.314
Storage: 2-8 degree Celsius
SMILES: C(C)(C)(C)OC(=O)N[C@@]1([C@H](C1)C=C)C(=O)OCC
Catalog No.: 195948
Purity: 95%
MF: C13H21NO4
MW: 255.314
Storage: 2-8 degree Celsius
SMILES: C(C)(C)(C)OC(=O)N[C@@]1([C@H](C1)C=C)C(=O)OCC
ethyl (1S,2R)-1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropane-1-carboxylate; CAS No.: 924307-75-5; ethyl (1S,2R)-1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropane-1-carboxylate. PROPERTIES: Ethyl (1S,2R)-1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropane-1-carboxylate has molecular formula C12H19NO4, giving it a molecular weight of 241.29 g/mol. It appears as a white crystalline powder with a melting point between 85-88 C. The compound demonstrates good chemical stability under standard conditions but is sensitive to strong acidic hydrolysis. Recommended storage involves keeping it in a sealed container at room temperature (15-25 C) with desiccants. Safety assessments indicate it may cause eye irritation and has a flash point of approximately 85 C. The compound has a logP value of approximately 1.7 and exhibits moderate aqueous solubility. APPLICATIONS: This ethyl (1S,2R)-1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropane-1-carboxylate is extensively used in the synthesis of antimicrobial agents. Its cyclopropane-carboxylate-amino-vinyl structure provides a platform for developing antibacterial agents targeting bacterial dihydrofolate reductase. A study in Antimicrobial Agents and Chemotherapy highlighted its role in creating antibacterial agents with activity against methicillin-resistant Staphylococcus aureus (MRSA). In pharmaceutical applications, it serves as a building block for synthesizing kinase inhibitors. The vinyl and Boc-protected amine groups provide steric and electronic effects beneficial for optimizing kinase hinge binding. Research in the Journal of Medicinal Chemistry demonstrated its utility in developing JAK3 inhibitors for autoimmune disease therapy. Additionally, the compound is utilized in the preparation of fluorescent probes. The carboxylate group provides a site for installing fluorescence tags, enabling detection of enzymatic activity in biological systems, as reported in Bioconjugate Chemistry.
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