320399-75-5

Basic information

• Product Name: (Z)-5-benzyldimethylsilyl-3-phenyl-4-penten-1-ol
• Synonyms: (Z)-5-benzyldimethylsilyl-3-phenyl-4-penten-1-ol
• CAS NO: 320399-75-5
• Molecular Weight: 310.511
• Mol File: 320399-75-5.mol

Chemical Properties

• CAS DataBase Reference: (Z)-5-benzyldimethylsilyl-3-phenyl-4-penten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-5-benzyldimethylsilyl-3-phenyl-4-penten-1-ol(320399-75-5)
• EPA Substance Registry System: (Z)-5-benzyldimethylsilyl-3-phenyl-4-penten-1-ol(320399-75-5)

Safety Data

• Hazardous Substances Data: 320399-75-5(Hazardous Substances Data)

Upstream product

• 6921-34-2 benzylmagnesium chloride 
• 220801-86-5 3-phenyl-4-pentyn-1-ol 
• 1833-31-4 benzyl(chloro)dimethylsilane 
• 320399-95-9 3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne 
• 320400-14-4 5-benzyldimethylsilyl-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne 

Downstream Products

• 259874-80-1 2-[(Z)-5-(Benzyl-dimethyl-silanyl)-3-phenyl-pent-4-enyl]-isoindole-1,3-dione 
• 259874-79-8 N-((Z)-5-benzyldimethylsilyl-3-phenyl-4-pentenyl)-p-toluenesulfonamide 
• 80816-30-4 3-phenyl-4-pentenol 
• 639086-31-0 (Z)-5-benzyldimethylsilyl-3-phenyl-4-pentenoic acid 

Relevant articles and documents

Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group: A new method for stereoselective synthesis of disubstituted tetrahydrofurans

In the presence of a catalytic amount of TsOH or TiCl4, (Z)-5-silyl-4-penten-1-ols ((Z)-1) are smoothly cyclized to 2-silylmethyl-substituted tetrahydrofurans. This cyclization is applicable to the construction of a tetrahydropyran ring. The silyl group and the geometry of the C-C double bond strongly influence the cychzation rate. TBDMS and benzyldimethylsilyl groups considerably accelerate the cyclization in comparison with a dimethylphenylsilyl group, and (E)-vinylsilanes show much lower reactivity than the corresponding (Z)-isomers. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes 17, 19, and 21, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity. The silyl group of some cychzed products can be easily converted into a hydroxy group with stereochemical retention.

Acid-catalyzed cyclization of vinylsilanes bearing an amino group. Stereoselective synthesis of pyrrolidines

(FORMULA PRESENTED) In the presence of an acid catalyst, vinylsilanes 1 bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl)pyrrolidines 2. This cyclization was utilized for the stereoselective synthe