560119-45-1

Basic information

• Product Name: (2R,3S,5S,6R)-2-(4-quinolyl)-6-vinyl-1-azabicyclo[3.2.2]nonan-3-ol
• CAS NO: 560119-45-1
• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.3908
• Mol File: 560119-45-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 458.8°C at 760 mmHg
• Flash Point: 231.3°C
• Density: 1.2g/cm³
• Vapor Pressure: 3.27E-09mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: (2R,3S,5S,6R)-2-(4-quinolyl)-6-vinyl-1-azabicyclo[3.2.2]nonan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,5S,6R)-2-(4-quinolyl)-6-vinyl-1-azabicyclo[3.2.2]nonan-3-ol(560119-45-1)
• EPA Substance Registry System: (2R,3S,5S,6R)-2-(4-quinolyl)-6-vinyl-1-azabicyclo[3.2.2]nonan-3-ol(560119-45-1)

Safety Data

• Hazardous Substances Data: 560119-45-1(Hazardous Substances Data)

Upstream product

• 560119-43-9 methanesulfonic acid (quinolin-4-yl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methyl ester 

Relevant articles and documents

The First and Second Cinchona Rearrangement. Two Fundamental Transformations of Alkaloid Chemistry

Stereochemistry, products, and driving forces of the "first and second Cinchona rearrangement" have been investigated and a unified theory is presented. The first cage expansion affords [3.2.2]azabicyclic α-amino ether and is formulated via a configurationally stable bridgehead iminium ion and quasiequatorial nucleophilic attack. The second cage expansion affords β-functionalized [3.2.2]azabicycles. In this case a nonclassical nitrogen-bridged cation is postulated to account for retention of configuration and potential reversibility of the cage expansion. The second rearrangement is favored for the so-called cinch bases (6′-R = H) in trifluoroethanol. Stereoelectronic factors, electron demand at C9, ground state conformation, and solvent type are crucial in all cases. A two-step protocol for preparing 9-epi-configured Cinchona alkaloids from 9-nat precursors is described.