1418134-80-1

Basic information

• Product Name: C₁₅H₂₀NO⁽¹⁺⁾*C₂F₃O₂^(1-)
• CAS NO: 1418134-80-1
• Molecular Weight: 343.346
• Mol File: 1418134-80-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₁₅H₂₀NO⁽¹⁺⁾*C₂F₃O₂^(1-)(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₅H₂₀NO⁽¹⁺⁾*C₂F₃O₂^(1-)(1418134-80-1)
• EPA Substance Registry System: C₁₅H₂₀NO⁽¹⁺⁾*C₂F₃O₂^(1-)(1418134-80-1)

Safety Data

• Hazardous Substances Data: 1418134-80-1(Hazardous Substances Data)

Upstream product

• 407-25-0 trifluoroacetic anhydride 
• 60161-30-0 4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine 
• 616866-40-1 (1R,9S)-1-methyl-7-methyleneoctahydro-4H-quinolizin-4-one 
• 1418134-72-1 C₁₆H₂₉NOSi 
• 862672-54-6 (5R,6S)-6-allyl-5-methylpiperidin-2-one 

Downstream Products

• 67314-63-0 (-)-neothiobinupharidine 
• 30343-74-9 thionuphlutine B 
• 30343-72-7 thiobinupharidine 
• 4850-09-3 (-)-neothiobinupharidine 
• 30343-70-5 6,6'-dihydroxythionuphlutine B 

Relevant articles and documents

Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids

Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6′-dihydroxythiobinupharidine (+)-1a, (+)-6-hydroxythiobinupharidine (+)-1-b, (-)-6,6′-dihydroxythionuphlutine (-)-2-a, (-)-6,6′-dihydroxyneothiobinupharidine (-)-3a, and (+)-6,6′-dihydroxyneothionuphlutine (+)-4-a. The latter two have not been found in nature. We have also made each of their enantiomers (-)-1a-b, (+)-2a, (+)-3a, and (-)-4a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1-a-1b - for those instances in which the NMR spectra were obtained in CD3OD - to their corresponding CD3O-adducts. Our efforts provide for the first time apoptosis data for (-)-3a, (+)-4a, and all five non-natural enantiomers prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7′. Nuphars are speedy killers: For the first time several of the hydroxylated dimeric nuphar alkaloids and their unnatural enantiomers have been synthesized. First-ever apoptosis data for many of these compounds is provided.