193898-06-5

Basic information

• Product Name: 3-Buten-1-ol, 4,4-bis(2-methylphenyl)-, 4-methylbenzenesulfonate
• CAS NO: 193898-06-5
• Molecular Formula: C25H26O3S
• Molecular Weight: 406.546
• Mol File: 193898-06-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Buten-1-ol, 4,4-bis(2-methylphenyl)-, 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-1-ol, 4,4-bis(2-methylphenyl)-, 4-methylbenzenesulfonate(193898-06-5)
• EPA Substance Registry System: 3-Buten-1-ol, 4,4-bis(2-methylphenyl)-, 4-methylbenzenesulfonate(193898-06-5)

Safety Data

• Hazardous Substances Data: 193898-06-5(Hazardous Substances Data)

Upstream product

• 182317-41-5 2,2-di(2-tolyl)tetrahydrofuran 
• 932-31-0 ortho-tolylmagnesium bromide 
• 98-59-9 p-toluenesulfonyl chloride 
• 193898-05-4 4,4-Di-o-tolyl-but-3-en-1-ol 

Downstream Products

• 193898-16-7 1-(4,4-Di-o-tolyl-but-3-enyl)-4-phenyl-1,4-dihydro-pyridine-3-carboxylic acid 2-cyano-ethyl ester 
• 193898-25-8 1-(4,4-Di-o-tolyl-but-3-enyl)-6-phenyl-1,6-dihydro-pyridine-3-carboxylic acid 2-cyano-ethyl ester 
• 182317-46-0 4,4-di(2-tolyl)-3-butenyl iodide 
• 193898-01-0 1,1-bis(2-methylphenyl)-4-bromo-1-butene 

Relevant articles and documents

Synthesis of 4,4-bis(2-methylphenyl)-3-butenyl (and butyl) analogs of 4-phenyl-1,4- and 6-phenyl-1,6-dihydropyridine-3-carboxylic acids and their evaluation as neuronal GABA-uptake inhibitors

Treatment of 3-[2-(4,4-dimethyl-4,5-dihydrooxazolin-2-yl)]-4-phenyl-1,4-dihydropyridine (13) with NaH-DMSO, and then reaction with 1,1-bis(2-methylphenyl)-4-bromobutane (12c) afforded 1-[4,4-bis(2-methylphenyl)butyl]-3-[2-(4,4-dimethyl-4,5-dihydrooxazolin-2-yl)]- 4-phenyl-1,4-dihydropyridine (14). Reaction of methyl nicotinate with 2.1 equivalents 12c or 1,1-bis(2-methylphenyl)-4-bromo-1-butene (11b) afforded 4,4-bis(2-methylphenyl)butyl 1-[4,4-bis(2-methylphenyl)butyl]pyridinium-3-carboxylate bromide (17) or 4,4-bis(2-methylphenyl)-3-butenyl 1-[4,4-bis(2-methylphenyl)-3-butenyl]pyridinium-3-carboxylate bromide (18), respectively. The nonregioselective reaction of the pyridinium salts (17/18) with PhMgCl in THF at -23°C using a catalytic amount of CuI afforded a mixture of isomeric 4-phenyl-1,4-dihydropyridyl (21 or 22) and 6-phenyl-1,6-dihydropyridyl (27 or 28) products in a ratio of approximately 1:1. All attempts to hydrolyze the 4,4-bis(2-methylphenyl)butyl or 3-butenyl ester moiety of 21/22 or 27/28 to a carboxyl group resulted in decomposition products. In contrast, the corresponding 3-(2-cyanoethyl) esters (23, 24, 29, 30) were readily converted to the corresponding carboxyl analogs (25, 26, 31, 32) via a β-elimination reaction of acrylonitrile using the non-nucleophilic base DBU. The 4-phenyl-1,4-dihydropyridyl (14, 25, 26) and 6-phenyl-1,6-dihydropyridyl (27/28 or 31/32) compounds inhibited the in vitro uptake of [3H]GABA into striatal prisms in the 21-44% range at a 10-4 M test compound concentration, relative to the reference drug nipecotic acid (87% inhibition). Structure-activity correlations showed the dihydropyridyl C-3 substituent was a determinant of [3H]GABA uptake where the potency order was CO2H > 2-(4,4-dimethyl-4,5-dmydrooxazolin-2-yl) > CO2(CH2)3CH-(o-tolyl)2 and CO2(CH2)2CH=C-(o-tolyl)2. Compounds possessing C-3 and (or) N-1 CO2(CH2)3CH-(o-tolyl)2 substituents were generally more potent than analogs having CO2(CH2)2CH=C-(o-tolyl)2 substituents. In general, 1,6-dihydropyridyl compounds were more potent than the corresponding 1,4-dihydropyridyl isomers.