94059-92-4

Usage

Family

Alkynes

Structure

Six-carbon chain with a carbon-to-carbon triple bond

Reactivity

Highly reactive in organic chemical reactions

Functional groups

Two methoxy groups (methyl group bonded to an oxygen atom)

Participation in chemical reactions

Nucleophilic substitution, coordination with metal ions

Versatility

Can be used in organic synthesis and as a building block for more complex molecules.

Upstream product

• 29882-07-3 4-chlorobutanal dimethyl acetal 
• 29329-03-1 5-hexynal 
• 149-73-5 trimethyl orthoformate 
• 91988-32-8 4-iodobutyraldehyde dimethyl acetal 
• 70277-75-7 lithium acetylide 
• 67-56-1 methanol 

Downstream Products

• 1420293-09-9 N-benzylidene-2-methoxy-2-oxo-1-(4,4,5,5-tetramethyl-2-(pent-4-yn-1-yl)-1,3-dioxolan-2-yl)ethanamine oxide 
• 38445-62-4 1-methoxy-3-methyl-2-cyclohexene 

Relevant academic research and scientific papers

Functional-group-tolerant catalytic migratory oxidative coupling of nitrones

A copper-catalyzed migratory oxidative-coupling reaction between nitrones and various ethers/amines exhibited high functional-group tolerance. Even in aqueous media, the reaction proceeded efficiently. For practical use of this catalysis, a unique sequent

Stereoselective Synthesis of Alcohols, XL - Stereoselective Cyclization of 7-Oxo-2-heptenylboronates

Intramolecular allylboration reaction of 7-oxo-2-heptenyl boronates leads to 2-vinylcyclopentanols.The cyclization proceeds in a stereospecific manner, such that the (E)-allylboronate 8 is converted into trans-2-vinylcyclopentanol (2) and the (Z)-allylboronate 10 into cis-2-vinylcyclopentanol (3).Asymmetric induction originating from stereogenic centers placed between the boronate and the aldehyde function has been found to be low. Key words: Cyclization, stereoselective / Allylboration, intramolecular

Controlling the Outcome of a Carbocation-initiated Cyclisation

The Z- and E-vinylsilanes, 6,6-dimethoxy-2-methyl-1-trimethylsilylhex-1-ene (6), gave only 3-methoxy-1-methylcyclohexene (7) on treatment with zinc bromide, and the allylsilane, 6,6-dimethoxy-2-methyl-3-trimethylsilylhex-1-ene (8), gave only 5-methoxy-1-methylcyclohexene (9) on treatment with tin(IV) chloride.Taken together with an earlier result, these results show that the silyl group completely controls the outcome of this carbocationic cyclisation.The syntheses of the two starting materials, (6) and (8), illustrate the usefulness of the silyl-cuprate reagent in the costruction of specific vinyl- and allyl-silanes.