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

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

• 864909-03-5 dimethyl-{5-methyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-hex-5-en-1-ynyl}-phenyl-silane 
• 864908-92-9 Dimethyl-phenyl-{(Z)-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-hept-5-en-1-ynyl}-silane 
• 864909-02-4 {6,6-diphenyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-hex-5-en-1-ynyl}-dimethyl-phenyl-silane 
• 864908-99-6 dimethyl-{6-methyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-hept-5-en-1-ynyl}-phenyl-silane 
• 198411-16-4 (E)-5-bromo-5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentene 
• 259874-71-0 N-((Z)-5-dimethylphenylsilyl-4-pentenyl)-p-toluenesulfonamide 
• 81097-24-7 N-tosyl-(4-pentenyl)amine 
• 259874-72-1 (Z)-5-(Dimethyl-phenyl-silanyl)-pent-4-enylamine 
• 174503-78-7 (Z)-5-dimethylphenylsilyl-1-phenyl-4-penten-1-ol 
• 174503-79-8 (Z)-1-dimethylphenylsilyl-1-undecen-5-ol 
• 174503-80-1 (Z)-7-dimethylphenylsilyl-2-methyl-6-hepten-3-ol 
• 320399-48-2 (E)-5-(dimethyl(phenyl)silyl)pent-3-en-1-ol 
• 821-09-0 n-Pent-4-enyl alcohol 

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.

1,2-Silyl-migrative cyclization of vinylsilanes bearing a hydroxy group: Stereoselective synthesis of multisubstituted tetrahydropyrans and tetrahydrofurans

Acid-catalyzed intramolecular addition of a hydroxy group to α-alkylated vinylsilanes has been studied. Treatment of (Z)-5-alkyl-5-silyl-4-penten-1-ols 1 (R = alkyl) with 5 mol % TiCl4 in CHCl3 gave trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis = > 99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the C-C double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis-selectivity. In the cyclization of (Z)-1 (R = Bu), the silyl group used, the reaction time, and the yield of 2 were as follows: SiMe2Ph, 9.5 h, 75%; SiMe3, 7.5 h, 66%; SiMePh2, 24 h, 58%; SiMe2-t-Bu, 0.75 h, 85%; SiMe2Bn, 1.5 h, 78%. This 1,2-silyl-migrative cyclization could be applied to stereoselective synthesis of trisubstituted tetrahydropyrans. The acid-catalyzed reaction of 1-, 2-, or 3-substituted (Z)-5-silyl-4-nonen-1-ols 8 gave r-2,t-3,c-6-, r-2,t-3,t-5-, or r-2,t-3,c-4-trisubstituted tetrahydropyrans with high diastereo-selectivity, respectively. (Z)-4-Alkyl-4-silyl-3-buten-1-ols 5 as well as 1 underwent the 1,2-silylmigrative cyclization to give 2-alkyl-3-silyltetrahydrofurans 6 with high trans-selectivity. This silicon-directed cyclization was also available for the stereoselective synthesis of tri- and tetrasubstituted tetrahydrofurans.

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