147918-38-5

Basic information

• Product Name: <14-(3-Pyridyl)-11-tetradecinyl>-p-toluolsulfonat
• Synonyms: <14-(3-Pyridyl)-11-tetradecinyl>-p-toluolsulfonat
• CAS NO: 147918-38-5
• Molecular Weight: 441.635
• Mol File: 147918-38-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: <14-(3-Pyridyl)-11-tetradecinyl>-p-toluolsulfonat(CAS DataBase Reference)
• NIST Chemistry Reference: <14-(3-Pyridyl)-11-tetradecinyl>-p-toluolsulfonat(147918-38-5)
• EPA Substance Registry System: <14-(3-Pyridyl)-11-tetradecinyl>-p-toluolsulfonat(147918-38-5)

Safety Data

• Hazardous Substances Data: 147918-38-5(Hazardous Substances Data)

Upstream product

• 147918-35-2 3-(4,4-Dibrom-3-butenyl)pyridin 
• 147918-36-3 3-(but-3-yn-1-yl)pyridine 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 53463-68-6 1-bromo-10-decanol 
• 1802-16-0 3-(3-pyridinyl)propionaldehyde 
• 2859-67-8 3-(3-pyridyl)propan-1-ol 
• 147918-37-4 14-(pyridin-3-yl)tetradec-11-yn-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant articles and documents

Synthese der Theonelladine A, B, C, D und von Niphatesin A

The pyridine alkaloids theonelladine A-D (1-4) and niphatesine (5) of marine origin have been synthesized starting either from 3-(4,4-dibromo-3-butenyl)pyridine (6) or from 3-pyridinecarbaldehyde.Reaction of 6 with two equivalents of BuLi gave the lithiated derivative of the alkyne 7, which could be alkylated with 1-bromo-10-(tetrahydro-2-pyranyloxy)decane (8) to yield the alkynol 9 after methanolysis.Selective hydrogenation of 9 with Lindlar palladium catalyst gave (Z)-14-(3-pyridyl)-11-tetradecen-1-ol (11). - Addition of the Grignard reagent of 12-(benzyloxy)-1-bromododecane (13) to 3-pyridinecarbaldehyde gave 17, which was first oxidized (Swern) to give 18 and then reduced (Wolff-Kishner) to give 14.Hydrogenolysis of the benzyl ether 14 yielded 15.The alcohol group in 9, 11, and 15 was converted into the tosyloxy group by reaction with tosyl chloride/pyridine.Subsequent reactions of the tosylates 10, 12, and 16 either with an excess of methylamine/ethanol or of ammonia/ethanol gave the pyridine alkaloids 1-5 in high yields as p-toluenesulfonates. Key Words: Pyridines/Alkaloids/Theonelladines A-D/Niphatesine A/4-(3-Pyridyl)-1-butin.