303176-37-6

Basic information

• Product Name: 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol
• Synonyms: 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol
• CAS NO: 303176-37-6
• Molecular Weight: 310.484
• Mol File: 303176-37-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol(303176-37-6)
• EPA Substance Registry System: 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol(303176-37-6)

Safety Data

• Hazardous Substances Data: 303176-37-6(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 303176-36-5 ethyl 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-2-pentenoate 
• 303176-35-4 3-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-1-propanol 
• 783332-57-0 3-(2-((tert-butyldimethylsilyl)oxy)-5-fluorophenyl)propanal 
• 303176-34-3 2-alllyl-1-(tert-butyldimethylsilyloxy)-4-fluoro-benzene 
• 13997-72-3 1-allyl-2-hydroxy-5-fluorobenzene 
• 13990-72-2 1-allyloxy-4-fluorobenzene 
• 371-41-5 4-Fluorophenol 

Downstream Products

• 593251-66-2 Carbonic acid (E)-5-(5-fluoro-2-hydroxy-phenyl)-pent-2-enyl ester methyl ester 
• 303176-44-5 2-(1,2-di(4-nitrophenylcarbonyloxy)-(1R)-ethyl)-6-fluoro-(2R)-3H,4H-chromene 
• 303176-46-7 (R)-2-[(R)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl-4-methylbenzenesulfonate 
• 303176-40-1 (R)-2-[(S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl-4-methylbenzenesulfonate 
• 303176-43-4 1-[6-fluoro-(2R)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol 
• 303176-45-6 1-[6-fluoro-(2R)-3,4-dihydro-2H-benzopyran-2-yl]-(1R)-1,2-ethylene glycol 
• 303176-39-8 1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1R)-1,2-ethylene glycol 
• 303176-42-3 (R)-2-amino-1-[(S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]ethanol 
• 197706-50-6 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran 
• 152520-56-4 d-nebivolol hydrochloride 
• 303176-38-7 5-(5-fluoro-2-hydroxy-phenyl)-E-2-penten-1-ol 

Relevant articles and documents

Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): Scope, mechanism, and applications

The Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol allyl carbonates serves as an efficient strategy to construct the allylic C-O bond allowing access to chiral chromans in up to 98% ee. The effect of pH and the influence of olefin geometry, as well as substitution pattern on the ee and the absolute configuration of the chiral chromans were explored in detail. These observations suggest a mechanism involving the cyclization of the more reactive π-allyl palladium diastereomeric intermediate as the enantiodiscriminating step (Curtin-Hammett conditions). This methodology led to the enantioselective synthesis of the vitamin E core, the first enantioselective total synthesis of (+)-clusifoliol and (-)-siccanin, and the synthesis of an advanced intermediate toward (+)-rhododaurichromanic acid A.