168960-95-0

Basic information

• Product Name: 9S-Amino-9-deoxyquinine
• Synonyms: 9S-Amino-9-deoxyquinine;9-Amino(9-deoxy)epi-quinine trihydrochloride;(1S)-(6-Methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)MethanaMine;(8α,9S)-9-amine-6'-methoxy-Cinchonan;(8α,9S)-6'-Methoxy-cinchonan-9-amine Trihydrochloride,99%e.e.;(S)-(6-Methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine
• CAS NO: 168960-95-0
• Molecular Formula: C₂₀H₂₅N₃O
• Molecular Weight: 323.432
• Mol File: 168960-95-0.mol

Chemical Properties

• Boiling Point: 484.846 °C at 760 mmHg
• Flash Point: 247.026 °C
• Appearance: /
• Density: 1.187 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.42±0.70(Predicted)
• CAS DataBase Reference: 9S-Amino-9-deoxyquinine(CAS DataBase Reference)
• NIST Chemistry Reference: 9S-Amino-9-deoxyquinine(168960-95-0)
• EPA Substance Registry System: 9S-Amino-9-deoxyquinine(168960-95-0)

Safety Data

• Hazardous Substances Data: 168960-95-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9S-Amino-9-deoxyquinine is used as a potential antimalarial agent for its ability to combat malaria, a disease caused by parasites that infect red blood cells. Its structure and pharmacological properties make it a candidate for further development in this area.
Used in Antiviral Applications:
9S-Amino-9-deoxyquinine is being investigated for its potential antiviral activities, suggesting that it could be utilized in the development of treatments for viral infections.
Used in Drug Synthesis:
9S-Amino-9-deoxyquinine is used as a building block in the synthesis of new drug candidates, with the aim of creating medications with improved properties, such as increased efficacy or reduced side effects.
Further research is necessary to fully understand the potential applications and benefits of 9S-Amino-9-deoxyquinine, as its pharmacological profile and therapeutic potential are still being explored.

InChI:InChI=1S/C20H25N3O/c1-3-13-12-23-9-7-14(13)10-19(23)20(21)16-6-8-22-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20H,1,7,9-10,12,21H2,2H3

Upstream product

• 130-95-0 quinine 

Downstream Products

• 852913-16-7 C₂₉H₂₈F₆N₄OS 

Relevant articles and documents

Cooperative Catalysis with Coupled Chiral Induction in 1,3-Dipolar Cycloadditions of Azomethine Ylides

1,3-Dipolar cycloadditions (1,3-DC) between imino esters (as precursors of N-metallated azomethine ylides) and π-deficient alkenes are promoted by cooperative asymmetric Lewis acid/Br?nsted base catalysis. The components of these catalytic pairs are silver salts derived from enantiopure commercially available BINOL-based phosphoric acids and Cinchona alkaloids. Chiral phosphoric silver(I) salts promote HOMO raising of in situ formed 1,3-dipoles, whereas protonated cinchona alkaloids generate a LUMO lowering for the dipolarophiles resulting in a global acceleration of the 1,3-DC. The best results were obtained with BINOL-derived silver phosphate and hydrocinchonine. Matching between both cooperative metallo- and organocatalyst results in an enhanced enantiomeric excess, superior to that reached by both separate components. NOESY experiments and DFT calculations are compatible with a non-covalent interaction (hydrogen bond) between both catalysts, which results in close contacts and mutually coupled chiral environments.

Organocatalytic enantioselective Michael addition of β-diketones to β-nitrostyrene: The first Michael addition of dipivaloylmethane to an activated olefin

The addition of a family of β-diketones to β-nitrostyrene was explored using a library of cinchona organocatalysts. A thiourea organocatalyst, under improved reaction conditions, is shown to be much more efficient at catalyzing this reaction than previously reported giving excellent yields and enantioselectivites (up to 95% yield and 97% ee). The same thiourea organocatalyst was employed in the first successful Michael addition of the sterically challenging dipivaloylmethane to β-nitrostyrene (99% ee). ARKAT-USA, Inc.