7688-58-6

Basic information

• Product Name: (3S)-2,3,4,10-Tetrahydro-3-hydroxy-2,2,10-trimethyl-5H-pyrano[2,3-b]quinolin-5-one
• Synonyms: (3S)-2,3,4,10-Tetrahydro-3-hydroxy-2,2,10-trimethyl-5H-pyrano[2,3-b]quinolin-5-one;Ribalinine
• CAS NO: 7688-58-6
• Molecular Formula: C15H17NO3
• Molecular Weight: 259.3004
• Mol File: 7688-58-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 232-233 °C(Solv: acetone (67-64-1))
• Boiling Point: 393.5°Cat760mmHg
• Flash Point: 191.8°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 6.72E-07mmHg at 25°C
• Refractive Index: 1.624
• PKA: 13.54±0.40(Predicted)
• CAS DataBase Reference: (3S)-2,3,4,10-Tetrahydro-3-hydroxy-2,2,10-trimethyl-5H-pyrano[2,3-b]quinolin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-2,3,4,10-Tetrahydro-3-hydroxy-2,2,10-trimethyl-5H-pyrano[2,3-b]quinolin-5-one(7688-58-6)
• EPA Substance Registry System: (3S)-2,3,4,10-Tetrahydro-3-hydroxy-2,2,10-trimethyl-5H-pyrano[2,3-b]quinolin-5-one(7688-58-6)

Safety Data

• Hazardous Substances Data: 7688-58-6(Hazardous Substances Data)

Usage

Uses

Unfortunately, the provided materials do not specify any particular applications or uses for (3S)-2,3,4,10-Tetrahydro-3-hydroxy-2,2,10-trimethyl-5H-pyrano[2,3-b]quinolin-5-one. However, given that it is a pyranoquinolone alkaloid, it may have potential applications in various fields such as pharmaceuticals, agrochemicals, or as a natural product with biological activity, similar to other alkaloids. Further research and development would be required to explore and confirm its specific uses.

References

Corral, Orazi., Tetrahedron Lett., S83 (1967) Synthesis: Bowman, Grundon., 1. Chem. Soc., C, IS04 (1966)

InChI:InChI=1/C15H17NO3/c1-15(2)12(17)8-10-13(18)9-6-4-5-7-11(9)16(3)14(10)19-15/h4-7,12,17H,8H2,1-3H3

Upstream product

• 72855-84-6 (+)-(3S)-geibalansine 
• 74-88-4 methyl iodide 
• 7282-19-1 atanine 
• 88148-18-9 5-methoxy-2,2-dimethyl-(2H)-pyrano<2,3-b>quinoline 
• 155102-08-2 (-)-(3S,4S)-3,4-dihydro-3,4-epoxy-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline 
• 155102-07-1 (+)-(3R,4S)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline 
• 88148-17-8 3-bromo-10-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-oxa-9-aza-anthracene 

Relevant articles and documents

Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro- and dihydropyrano-quinoline alkaloids

The chiral quinoline alkaloids platydesmine 3, platydesmine methosalt 4 and edulinine 9, have been synthesised in enantiopure form via asymmetric dihydroxylation of the achiral alkaloid atanine 1. Chromatographic separation of MTPA diastereoisomers 20 formed from racemic bromohydrin derivatives of atanine 1 was a key step in the synthesis of geibalansine 7, edulinine 9, ribalinine 10, Ψ-ribalinine 11 and araliopsine 12 as single enantiomers. The absolute configurations of (+)-platydesmine methosalt 4 and (-)-Ψ-ribalinine 11 were unequivocally determined by X-ray crystallography while stereochemical correlation and circular dichroism spectroscopy methods were used to assign absolute configurations to platydesmine 3, geibalansine 7, ribalinine 10, araliopsine 12 and edulinine 9. Possible errors which earlier led to the incorrect assignment of absolute configurations of the quinoline alkaloids platydesmine 3, platydesmine methosalt 4, edulinine 9, araliopsine 12 and other related chiral quinoline alkaloids are discussed.