2-(1-ADAMANTYL)OXIRANE - CAS 28173-62-8

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Category
Main Product
Product Name
2-(1-ADAMANTYL)OXIRANE
Catalog Number
28173-62-8
Synonyms
CHEMBRDG-BB 4013915; 2-(1-ADAMANTYL)OXIRANE; AKOS BC-0493; UKRORGSYN-BB BBV-028015; oxirane, 2-tricyclo[3.3.1.1~3,7~]dec-1-yl-
CAS Number
28173-62-8
Molecular Weight
178.27
Molecular Formula
C12H18O
COA
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MSDS
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Canonical SMILES
C1C2CC3CC1CC(C2)(C3)C4CO4
InChI
InChI=1S/C12H18O/c1-8-2-10-3-9(1)5-12(4-8,6-10)11-7-13-11/h8-11H,1-7H2
InChIKey
PQZLOWONDMXBIN-UHFFFAOYSA-N
Structure
CAS 28173-62-8 2-(1-ADAMANTYL)OXIRANE
Specification
Purity
95%
Boiling Point
253.062ºC at 760 mmHg
Density
1.172g/cm3
Reference Reading
1.Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.
Wang HY1, Huang K1, De Jesús M1, Espinosa S1, Piñero-Santiago LE1, Barnes CL2, Ortiz-Marciales M1. Tetrahedron Asymmetry. 2016 Feb 15;27(2-3):91-100.
A practical and convenient method for the efficient and regio- and stereoselective ring-opening of enantiopure monosubstituted epoxides by sodium azide under hydrolytic conditions is reported. The ring-opening of enantiopure styryl and pyridyl (S)-epoxides by N3 - in hot water takes place preferentially at the internal position with complete inversion of configuration to produce (R)-2-azido ethanols with up to 99% enantio- and regioselectivity, while the (S)-adamantyl oxirane provides mainly the (S)-1-adamantyl-2-azido ethanol in excellent yield. In general, 1,2-amino ethanols were obtained in high yield and excellent enantiopurity by the reduction of the chiral 1,2-azido ethanols with PPh3 in water/THF, and then converted into the Boc or acetamide derivatives.
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