6-(t-Butyldimethylsilyloxy)-1-hexyne

Base Information

• Chemical Name: 6-(t-Butyldimethylsilyloxy)-1-hexyne
• CAS No.: 73448-13-2
• Molecular Formula: C12H24OSi
• Molecular Weight: 212.407
• DSSTox Substance ID: DTXSID50451745
• Nikkaji Number: J1.021.143C
• Wikidata: Q82271935
• Mol file: 73448-13-2.mol

Synonyms:73448-13-2;6-(tert-Butyldimethylsilyloxy)-1-hexyne;6-(t-butyldimethylsilyloxy)-1-hexyne;tert-butyl-hex-5-ynoxy-dimethylsilane;TERT-BUTYL(HEX-5-YN-1-YLOXY)DIMETHYLSILANE;starbld0040139;SCHEMBL662237;1-t-butyldimethylsiloxyhex-5-yne;DTXSID50451745;RWFYLLBXPPJCCD-UHFFFAOYSA-N;AKOS030254950;6-(tert-Butyldimethylsiloxy)-1-hexyne;tert-Butyl-hex-5-ynyloxy-dimethyl-silane;CS-0455280;(1,1-dimethylethyl)(5-hexynyloxy)dimethylsilane

Chemical Property of 6-(t-Butyldimethylsilyloxy)-1-hexyne

Chemical Property:

• PSA: 9.23000
• LogP: 3.81170
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 212.159641919
• Heavy Atom Count: 14
• Complexity: 204

Purity/Quality:

99% ^*data from raw suppliers

6-(tert-Butyldimethylsilyloxy)-1-hexyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCCCCC#C
• Uses: 6-(tert-Butyldimethylsilyloxy)-1-hexyne is an intermediate in the synthesis 2-substituted cyclobutanones as γ-irradiation marker products of lipid-containing foods.

Technology Process of 6-(t-Butyldimethylsilyloxy)-1-hexyne

There total 11 articles about 6-(t-Butyldimethylsilyloxy)-1-hexyne which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5-hexyl-1-ol (928-90-5) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethylsilyl hex-5-yn-1-yl ether (73448-13-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00347-0

Reference yield: 94.0%

1,1-dibromo-6-(tert-butyldimethylsiloxy)hex-1-ene (306734-44-1) → tert-butyldimethylsilyl hex-5-yn-1-yl ether (73448-13-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 23 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b03557

Reference yield: 93.0%

6-(t-butyldimethylsilyloxy)-1-trimethylsilylhex-1-yne (150422-67-6) → tert-butyldimethylsilyl hex-5-yn-1-yl ether (73448-13-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; acetonitrile; at 60 ℃; for 6h;

DOI:10.1055/s-2008-1032078

upstream raw materials:

lithium acetylide-ethylenediamine complex

1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane

5-hexyl-1-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

7-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hept-2-yn-1-one

9-(tert-butyldimethylsilyloxy)-1-phenylnon-4-yn-3-yl methyl carbonate

9-hydroxy-2,2-dimethyl-1-phenylnon-4-yn-3-yl methyl carbonate

Refernces

• 1、 Attygalle, Athula B.,Herath, Kithsiri B.,Meinwald, Jerrold. "Cycloalkene Budding: A Unique Rearrangement Observed in the Mass Spectra of N,N-Dimethylhydrazones of Unsaturated Aldehydes". . p. 408 - 410. Retrieved 1998.
• 2、 Yoshizaki, Hiroki,Tanaka, Tadashi,Yoshii, Eiichi,Koizumi, Toru,Takeda, Kei. "Asymmetric reductive cyclization using the intramolecular conjugate addition of enolates onto α,β-unsaturated sulfoxides". . p. 47 - 50. Retrieved 1998.
• 3、 Ding, Lu,Song, Hao,Zheng, Chao,You, Shu-Li. "Enantioselective Synthesis of Medium-Sized-Ring Lactones via Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reaction". supporting information. p. 4770 - 4775. Retrieved 2022/03/27.
• 4、 Asari, Austin H.,Floreancig, Paul E.. "Dictating Thermodynamic Control through Tethering: Applications to Stereoselective Bis-Spiroketal Synthesis". supporting information. p. 6622 - 6626. Retrieved 2020/03/04.