198411-11-9

Basic information

• Product Name: 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne
• Synonyms: 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne
• CAS NO: 198411-11-9
• Molecular Weight: 302.489
• Mol File: 198411-11-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne(CAS DataBase Reference)
• NIST Chemistry Reference: 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne(198411-11-9)
• EPA Substance Registry System: 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne(198411-11-9)

Safety Data

• Hazardous Substances Data: 198411-11-9(Hazardous Substances Data)

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 5390-04-5 pent-1-yn-5-ol 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 864908-99-6 dimethyl-{6-methyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-hept-5-en-1-ynyl}-phenyl-silane 
• 198411-19-7 (Z)-5-dimethylphenylsilyl-5-iodo-1-(2-tetrahydropyranyloxy)-4-pentene 
• 460752-67-4 (Z)-5-dimethylphenylsilyl-8-p-methoxybenzyloxy-1-(2-tetrahydropyranyloxy)-4-octene 
• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 
• 198410-85-4 (Z)-5-dimethylphenylsilyl-4-hexen-1-ol 
• 198410-89-8 (Z)-5-dimethylphenylsilyl-5-trimethylsilyl-4-penten-1-ol 
• 198410-88-7 (Z)-5-dimethylphenylsilyl-5-phenyl-4-penten-1-ol 
• 198410-78-5 (Z)-5-dimethylphenylsilyl-4-nonen-1-ol 
• 198411-05-1 (E)-5-dimethylphenylsilyl-4-nonen-1-ol 
• 198410-87-6 (Z)-8-acetoxy-5-dimethylphenylsilyl-4-octen-1-ol 

Relevant articles and documents

Radical cyclizations leading to the bicyclo[2.2.1]heptane framework: A new radical approach to (±)-(Z)-β-santalol

Tandem radical cyclizations of acyclic iodides, including [3-(2-iodoethyl)-6,10-dimethyl-undeca-5,9-dien-1-ynyl]-dimethylphenylsilane lead in good yields to bicyclo[2.2.1]heptane derivatives. The cascade relies on two sequential radical-mediated 5-exo-cyclizations. The radical approach is illustrated with the total synthesis of racemic-(Z)-β-santalol. The results are remarkable, two fused rings and one stereogenic center are formed in a single operation. A new 'coordinated' hydride appeared to be useful in the cascade.

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.