73448-13-2

Basic information

• Product Name: Silane, (1,1-dimethylethyl)(5-hexynyloxy)dimethyl-
• Synonyms: (1,1-dimethylethyl)(5-hexynyloxy)dimethylsilane;t-butyl(5-hexynyloxy)dimethylsilane;Silane,(1,1-dimethylethyl)(5-hexynyloxy)dimethyl;tert-butylhex-5-ynyloxydimethylsilane;1-t-butyldimethylsiloxyhex-5-yne;6-(t-butyldimethylsilyloxy)-1-hexyne;t-butyl(hex-5-yn-1-yloxy)dimethylsilane;tert-butyl (hex-5-yn-1-yloxy)dimethylsilane
• CAS NO: 73448-13-2
• Molecular Formula: C12H24OSi
• Molecular Weight: 212.407
• Mol File: 73448-13-2.mol
• Article Data: 54

Chemical Properties

• CAS DataBase Reference: Silane, (1,1-dimethylethyl)(5-hexynyloxy)dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (1,1-dimethylethyl)(5-hexynyloxy)dimethyl-(73448-13-2)
• EPA Substance Registry System: Silane, (1,1-dimethylethyl)(5-hexynyloxy)dimethyl-(73448-13-2)

Safety Data

• Hazardous Substances Data: 73448-13-2(Hazardous Substances Data)

Usage

Uses

6-(tert-Butyldimethylsilyloxy)-1-hexyne is an intermediate in the synthesis 2-substituted cyclobutanones as γ-irradiation marker products of lipid-containing foods.

Upstream product

• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 92511-12-1 1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane 
• 928-90-5 5-hexyl-1-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 70277-75-7 lithium acetylide 
• 150422-67-6 6-(t-butyldimethylsilyloxy)-1-trimethylsilylhex-1-yne 
• 335428-11-0 tert-butyl((6-iodohex-5-yn-1-yl)oxy)dimethylsilane 
• 111-29-5 1 ,5-pentanediol 
• 83067-20-3 5-(tert-butyldimethyl-silyloxy)pentan-1-ol 
• 87184-80-3 5-tert-butyldimethylsilyloxypentanal 
• 306734-44-1 1,1-dibromo-6-(tert-butyldimethylsiloxy)hex-1-ene 

Downstream Products

• 195535-07-0 tert-butyl-(6-cyclohexylhex-5-ynyloxy)dimethylsilane 
• 201871-85-4 (R)-6-[[tert-butyl(dimethyl)silyl]oxy]-1-hexynyl p-tolyl sulfoxide 
• 795280-02-3 (E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-3-methyl-hept-2-en-1-ol 
• 880085-69-8 9-(tert-butyldimethylsilyloxy)-1-phenylnon-4-yn-3-yl methyl carbonate 
• 880085-61-0 9-hydroxy-2,2-dimethyl-1-phenylnon-4-yn-3-yl methyl carbonate 
• 683246-81-3 N-benzyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-hex-1-ynyl]-4-methyl-benzenesulfonamide 
• 73416-71-4 (5Z,7E)-5,7-dodecadien-1-ol 
• 252947-95-8 4-[6-(t-butyldimethylsilyloxy)-1-hexynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman 

Relevant articles and documents

Strictly regio- and stereo-controlled α-alkenylation of bicyclic enone derivatives via palladium-catalyzed cross coupling and its application to a formal synthesis of (±)-carbacyclin

A formal synthesis of carbacylin was achieved by preparing a known advanced intermediate 15 via Zr-promoted enyne bicyclization-carbonylation, Pd-catalyzed α-alkenylation of bicyclic enones, and conjugate reduction.

Towards the total synthesis of octalactin A

In the course of a total synthesis of octalactin A, the (C1-C7) and (C8- C15) sub-units have been built up using catalytic asymmetric reactions; specifically, an asymmetric Shi epoxidation and a vinylogous Mukaiyama-aldol reaction.

Activation of 7-Endo over 6-Exo Epoxide Openings. Synthesis of Oxepane and Tetrahydropyran Systems

Activation of 7-endo over 6-exo hydroxy epoxide opening by placement of an electron-rich double bond furthest away from the hydroxyl group leads to a reliable entry into trans- and cis-substituted oxepane systems.The scope and limitations of the method are discussed and extensions to bicyclic systems are presented.

Diethylzinc-Mediated Radical 1,2-Addition of Alkenes and Alkynes

A novel diethylzinc-mediated radical 1,2-addition of perfluoroalkyl iodides to unactivated alkenes and alkynes is presented, which demonstrates a novel way to generate an ethyl difluoroacetate radical. This method is highly efficient and gives full conversions of the substrates, high yields of the products, and negligible byproducts and requires no column chromatography purifications. The mild conditions enable this protocol to exhibit excellent functional group compatibility.

Stereoselective Csp3?Csp2 Cross-Couplings of Chiral Secondary Alkylzinc Reagents with Alkenyl and Aryl Halides

We report palladium-catalyzed cross-coupling reactions of chiral secondary non-stabilized dialkylzinc reagents, prepared from readily available chiral secondary alkyl iodides, with alkenyl and aryl halides. This method provides α-chiral alkenes and arenes with very high retention of configuration (dr up to 98:2) and satisfactory overall yields (up to 76 % for 3 reaction steps). The configurational stability of these chiral non-stabilized dialkylzinc reagents was determined and exceeded several hours at 25 °C. DFT calculations were performed to rationalize the stereoretention during the catalytic cycle. Furthermore, the cross-coupling reaction was applied in an efficient total synthesis of the sesquiterpenes (S)- and (R)-curcumene with control of the absolute stereochemistry.