19780-83-7

Usage

Physical properties

Colorless liquid with a characteristic odor

Uses

Starting material in organic synthesis, solvent, intermediate in chemical reactions, trace amounts found in certain fruit and alcoholic beverages

Applications

Pharmaceuticals, agrochemicals, other industries

Reactivity

Ability to be used as a building block for the synthesis of other compounds

Hazardous

Requires careful handling due to potential hazards if not used properly

Upstream product

• 75-56-9 methyloxirane 
• 74-99-7 prop-1-yne 
• 5689-83-8 4-methyl-[1,3,2]dioxathiolane 2,2-dioxide 
• 97487-06-4 2,3-dimethyl-1-cyclobutenyl nonaflate 
• 97487-07-5 2,4-dimethyl-1-cyclobutenyl nonaflate 
• 75-89-8 2,2,2-trifluoroethanol 
• 18295-60-8 propargyl magnesium bromide 
• 16466-97-0 1-propynylmagnesium bromide 
• 78-75-1 1,2-Dibromopropane 
• 131863-89-3 tert-butyl-dimethyl-(1-methyl-prop-2-ynyloxy)-silane 
• 75-07-0 acetaldehyde 
• 2117-11-5 4-pentyn-2-ol 
• 74-88-4 methyl iodide 

Downstream Products

• 56539-63-0 Benzoic acid (E)-1-methyl-pent-3-enyl ester 
• 437703-13-4 Benzoic acid (3S,4S)-3,4-dihydroxy-1-methyl-pentyl ester 
• 437703-21-4 Benzoic acid 1-methyl-2-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 437703-15-6 Benzoic acid 2-((4S,5S)-2-ethoxy-2-ethoxycarbonylmethyl-5-methyl-[1,3]dioxolan-4-yl)-1-methyl-ethyl ester 
• 380228-64-8 5-(dimethyl-phenyl-silanyl)-4-hydroperoxy-hex-5-en-2-ol 

Relevant academic research and scientific papers

Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.

Development of an Alkyne Analogue of the de Mayo Reaction: Synthesis of Medium-Sized Carbacycles and Cyclohepta[b]indoles

Embedded medium-sized carbacycles and cyclohepta[b]indoles occur frequently as scaffold elements in natural products and bioactive compounds. Described herein is a conceptionally novel photochemically triggered cascade process to these scaffolds. Key to the cascading ring-expansion process is an unprecedented intramolecular alkyne analogue of the de Mayo reaction.

A detailed investigation of the aza-prins reaction

The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s). The Royal Society of Chemistry.

Synthesis of the C(1)-C(8) segment of (+)-acutiphycin

The synthesis of the pyran segment of (+)-acutiphycin was achieved using an intramolecular Lewis acid-catalyzed reaction between a silyl enol ether and an ortho ester.

Synthesis of 4,6-dideoxyfuranoses through the regioselective and diastereoselective oxyfunctionalization of a dimethylphenylsilyl-substituted chiral homoallylic alcohol

The 4,6-dideoxyfuranoses 10a and 10b have been synthesized by starting from the readily available E-5-dimethylphenylsilyl-2-hexene-4-ol (1)and employing successively three versatile oxyfunctionalization methods, namely photooxygenation, metal-catalyzed epoxidation, and oxidative desilylation. Photooxygenation of the hydroxy vinylsilane 1 and subsequent triphenylphosphine reduction of the hydroperoxides 3 afford the like-4a and unlike-4b diols, which have been converted separately to the tetrahydrofurans (2S*,3R*,5R*)-7a and (2S*,3R*,5S*)-7b by a combination of diastereoselective epoxidation and regioselective intramolecular epoxide-ring opening. In the epoxidation reaction, catalyzed by Ti(OiPr)4 or VO(acac)2, only one diastereomer (dr > 95:5) of the epoxide 5 is obtained. Further intramolecular opening of the epoxide ring in erythro-5 occurs regioselectively at the C-α position and diastereoselectively under inversion of the configuration of the silyl-substituted stereogenic center to generate only one diastereomer of the tetrasubstituted tetrahydrofurans 7. Oxidative desilylation of the latter gave the hitherto unknown 4,6-dideoxyfuranoses 10a and 10b. The use of the optically active E-5-dimethylphenylsilyl-2-hexene-4-ol (1) as starting material, which is readily available through lipase-catalyzed kinetic resolution, leads to the D- and L-4,6-dideoxysorbofuranoses 10a and D- and L-4,6-dideoxyfructofuranoses 10b in up to 98% enantiomeric excess.