172424-46-3

Basic information

• Product Name: (E)-tert-butyl(penta-2,4-dien-1-yloxy)diphenylsilane
• Synonyms: (E)-tert-butyl(penta-2,4-dien-1-yloxy)diphenylsilane
• CAS NO: 172424-46-3
• Molecular Weight: 322.522
• Mol File: 172424-46-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-tert-butyl(penta-2,4-dien-1-yloxy)diphenylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-tert-butyl(penta-2,4-dien-1-yloxy)diphenylsilane(172424-46-3)
• EPA Substance Registry System: (E)-tert-butyl(penta-2,4-dien-1-yloxy)diphenylsilane(172424-46-3)

Safety Data

• Hazardous Substances Data: 172424-46-3(Hazardous Substances Data)

Upstream product

• 1560-54-9 allyltriphenylphosphonium bromide 
• 115869-43-7 (tert-butyldiphenylsilanyloxy)acetaldehyde 
• 87770-83-0 (Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 131380-48-8 (E)-4-(t-butyldiphenylsilyl)oxy-2-butenal 
• 4949-20-6 (E)-2,4-pentadien-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 127793-64-0 (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 
• 100-53-8 phenylmethanethiol 
• 501364-98-3 (R)-1-O-(tert-butyldiphenylsilyl)-2-O-(p-tolylsulfonyl)-4-pentene-1,2-diol 

Downstream Products

• 1169707-72-5 (S,Z)-5-(tert-butyldiphenylsilyloxy)pent-2-ene-1,4-diol 
• 172424-45-2 methyl (E,E)-6,6-diphenyl-5,7,6-dioxasila-2,9,11-dodecadienoate 
• 4949-20-6 (E)-2,4-pentadien-1-ol 

Relevant articles and documents

Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles

We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.

Stereoselective synthesis of homochiral substituted tetrahydrothiophenes by electrophile-promoted thioetherification

In this paper we study the electrophile-promoted cyclization of 2-sulfanyl-4-penten-1-ol and 1-sulfanyl-4-penten-2-ol derivatives as a way of preparing cyclic sulfides. The reaction is completely chemoselective and always proceeds by activation of the sulfur centre. The reaction of 2-sulfanyl-4-penten-1-ol derivatives proceeds by a 5-endo mode. Unsaturated thiol 6 undergoes iodine-promoted cyclothioetherification to give the tetrahydrothiophene 9 in moderate yields and with excellent regio- and stereoselectivity. However, when the reaction starts from the benzyl sulfide 7, a diastereomeric mixture of 9 and 10 is obtained in good yields. Selenium-promoted cyclization of unsaturated thioacetate 5 provides the selenyltetrahydrothiophene 12 or the sulfanyl acetate 13, depending on the selenium reagent used. On the other hand, electrophile-induced cyclization of 1-sulfanyl-4-penten-2-ol derivatives 23-25 depends on the electrophile used. Iodothioetherification of benzyl sulfide 25 followed by oxidation affords unsaturated sulfone 26 as a result of 6-endo-cyclization, dehydroiodination and oxidation. In contrast, selenothiocyclization of 24 with PhSeX results in the formation of the 5-exo tetrahydrothiophenes 29/30 and/or 31/32. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.