61539-61-5

Basic information

• Product Name: 1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene
• Synonyms: 1,1-Dimethoxy-3-trimethylsilyloxy-1,3-butadiene;1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene
• CAS NO: 61539-61-5
• Molecular Formula: C₉H₁₈O₃Si
• Molecular Weight: 202.32292
• Mol File: 61539-61-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene(61539-61-5)
• EPA Substance Registry System: 1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene(61539-61-5)

Safety Data

• Hazardous Substances Data: 61539-61-5(Hazardous Substances Data)

Usage

Uses

3-(Trimethylsilyloxy)-1,1-dimethoxy-1,3-butadiene has a wide variety of applications in synthetic chemistry. One example of its applications is its use as a reagent in the synthesis of Lasiodiplodin, a potent antileukemic macrolide.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 50473-61-5 4,4-dimethoxy-3-buten-2-one 

Downstream Products

• 28478-46-8 methyl 4-hydroxy-2-methoxybenzoate 
• 92511-96-1 1,7-bis(benzyloxy)-5-methoxy-4-naphthol 
• 88083-77-6 6-methoxy-2-phenyl-2,3-dihydropyran-4-onen 
• 28504-24-7 xanthopurpurin-1-methylether 
• 126-07-8 griseofulvin 
• 111737-33-8 4-(Cyanophenylmethylen)-6-methoxy-3,5-diphenylcyclohepta-2,6-dien-1-on 
• 111737-32-7 4-(Cyanophenylmethylen)-6-methoxy-3,5-diphenylcyclohepta-2,6-dien-1-on 
• 65212-19-3 4-hydroxy-6-methoxy-phthalic acid dimethyl ester 
• 65212-23-9 Methyl-2-methoxy-cyclohex-2-en-4-on-1-carboxylat 
• 65212-24-0 3-Methoxy-4-acetylcyclohex-2-en-1-on 
• 65212-21-7 methyl (5-hydroxy-3-methoxy-2-methoxycarbonylphenyl)acetate 
• 65565-48-2 2-chloro-5,7-dimethoxy-1,4-naphthoquinone 
• 71838-34-1 4-Hydroxy-2-methoxy-6-oct-7-enyl-benzoic acid methyl ester 

Relevant articles and documents

Addition of silyloxydienes to 2,6-dibromo-1,4-benzoquinone: An approach to highly oxygenated bromonaphthoquinones for the synthesis of thysanone

The synthesis of tetraoxygenated bromonaphthoquinones 6a, 6b, 6c, 6d, key intermediates for a synthesis of the 3C protease inhibitor, thysanone, were investigated. Addition of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene 8 to 2,6-dibromo-1,4-benzoquinone 10 in benzene afforded a mixture of naphthoquinone 6a, arising from Diels-Alder addition followed by aromatisation, and Michael adduct 12. The Michael adduct 12 predominated when THF was used as solvent whereas 6a predominated when benzene was used. Naphthoquinone 6a underwent benzylation to naphthoquinone 6c. Addition of 1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene 9 to 2,6-dibromo-1,4-benzoquinone 10 followed by benzylation failed to afford the desired bromonaphthoquinone 6d yet methylation did afford naphthoquinone 6b. Bromonaphthoquinone 6d was finally prepared from naphthol 18, obtained from addition of diene 9 to 1,4-benzoquinone 17, followed by ortho-bromination and oxidation. Attempted Sakurai allylation of bromonaphthoquinone 6d afforded naphthodihydrofuran 21. A similar observation was observed for 2-carbomethoxy-1,4-naphthoquinone 22 that also underwent Sakurai allylation to afford naphthodihydrofuran 23. The structure of Michael adduct 12 was confirmed by X-ray crystallography.