60723-43-5

Basic information

• Product Name: 9-Acetoxyrubanone
• Synonyms: (8R, 9S)-6'-Methoxy-3-oxoruban-9-yl Acetate;(8R,9S)-6-Methoxy-3-oxo-9-rubanol Acetate;(9S)-9-(Acetyloxy)-6'-methoxy-10,11-dinorcinchonan-3-one;6'-Methoxy-3-oxo-9-rubanol Acetate;9-Acetoxyrubanone;ICQ 9;(S)-(6-Methoxyquinolin-4-yl)((2R,4S)-5-oxoquinuclidin-2-yl)Methyl acetate
• CAS NO: 60723-43-5
• Molecular Formula: C₂₀H₂₂N₂O₄
• Molecular Weight: 354.404
• Product Categories: Chiral Reagents;Heterocycles
• Mol File: 60723-43-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 162-163°C
• Boiling Point: 524.34°C at 760 mmHg
• Flash Point: 270.911°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 9-Acetoxyrubanone(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Acetoxyrubanone(60723-43-5)
• EPA Substance Registry System: 9-Acetoxyrubanone(60723-43-5)

Safety Data

• Hazardous Substances Data: 60723-43-5(Hazardous Substances Data)

Usage

Chemical Properties

WHite Solid

Uses

An intermediate for the preparation of (3S)-3-Hydroxy Quinidine

InChI:InChI=1/C20H22N2O4/c1-12(23)26-20(18-9-13-6-8-22(18)11-19(13)24)15-5-7-21-17-4-3-14(25-2)10-16(15)17/h3-5,7,10,13,18,20H,6,8-9,11H2,1-2H3/t13?,18-,20+/m1/s1

Upstream product

• 53922-99-9 α-10-bromodihydroquinidine 
• 139237-97-1 (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol 
• 56-54-2 (+)-quinidine 
• 139239-49-9 apoquinidine methyl ether 9-acetate 

Downstream Products

• 60723-44-6 (3S)-3-hydroxyquinidine 9-benzoate 
• 60761-51-5 (3R)-3-hydroxyquinidine 
• 53467-23-5 3-hydroxyquinidine 

Relevant articles and documents

A Tricyclic Dehydrorubanone and New Isomers of the Major Quinidine Metabolite

Spiroepoxide 1 was prepared from quinidine and converted into β-amino alcohol 3 (86percent over two steps).Dihydroxylation of enantiopure oxazatricylic olefin (E)-4 provided diastereomeric diols 5a and 5b.Stereospecific conversion of 1,2-secondary, tertiary diol 5b into tetracyclic spiroepoxide 6 was accomplished in high yield by a one-pot tosylation-cyclization procedure. 1,2-Diol cleavage with NaIO4 in 80percent acetic acid afforded the new tricyclic dehydrorubanone 7, containing the 4-oxa-7-azatricyclo3,7>decan-2-one core structure.Similarly, acetylated rubanone 9 was prepared on a 20 g scale.Reduction with NaBH4 in the presence of CeCl3 provided rubanols 10a and 10b (1:1.1).Horner-Wittig reaction of 9 with diethyl cyanomethylphosphonate was (Z)-selective, furnishing unsaturated nitrile (Z)-13.Conversion into the α,β-unsaturated aldehyde (Z)-14 and reduction afforded enantiopure allylic alcohol (Z)-12, which is a new isomer of the key quinidine metabolite 15. - Keywords: amino alcohols; asymmetric ayntheses; dihydroxylations; diol cleavage Horner-Wittig reaction