1576-84-7

Usage

Uses

Used in Flavor and Fragrance Industry:
Acetic Acid 3-Buten-1-yl Ester is used as a flavoring agent for its fruity smell, which is somewhat similar to the aroma of apples or pineapples. It is particularly favored in the creation of artificial fruit flavors.
Used in Food Flavoring:
In the food industry, Acetic Acid 3-Buten-1-yl Ester is used as a flavor enhancer to impart apple-like flavors to various food products.
However, it is important to note that care must be taken when handling Acetic Acid 3-Buten-1-yl Ester, as it can cause skin and eye irritation, disturbances to the central nervous system, and digestive tract issues when swallowed.

InChI:InChI=1/C6H10O2/c1-3-4-5-8-6(2)7/h3H,1,4-5H2,2H3

Upstream product

• 627-27-0 homoalylic alcohol 
• 56703-55-0 but-3-yn-1-yl acetate 
• 628-67-1 butane-1,4-diol diacetate 
• 1117-31-3 1,3-diacetoxybutane 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 1576-98-3 trans-1,4-diacetoxy-2-butene 
• 75-36-5 acetyl chloride 
• 5162-44-7 1-bromo-4-butene 
• 143314-17-4 1-ethyl-3-methylimidazolium acetate 
• 108-05-4 vinyl acetate 
• 110-88-3 1,3,5-Trioxan 

Downstream Products

• 627-27-0 homoalylic alcohol 
• 106-98-9 1-butylene 
• 3681-82-1 acetic acid hex-3-enyl ester 
• 69182-63-4 diacetoxy-1,6 hexene-3 
• 110211-07-9 3-hydroxy-4-phenylthiobutyl acetate 
• 75668-72-3 N-<(E)-4-(1-Oxoethoxy)-2-butenylsulfinyl>-p-toluolsulfonamid 
• 74608-07-4 N-(1-Acetoxymethylallyl)-N-(p-toluolsulfonamidothio)-p-toluolsulfonamid 
• 116043-36-8 (E)-N-methyl-N-(1-buten-2-yl)-p-toluensulfonamide 
• 116043-37-9 N-methyl-N-(1-vinyl-3-butenyl)-p-toluensulfonamide 
• 97187-36-5 N-methyl-N'-(2,7-octadienyl)-p-toluenesulfamide 
• 36234-16-9 4-Acetoxyoxacyclohexan 
• 90371-05-4 4-(2-acetoxy-ethyl)-[1,3]dioxane 
• 38551-66-5 1,3,5-Triacetoxy-pentan 
• 870650-23-0 tert-butyl (+)-2-(4-acetoxybutyl)-2-methyl-6-oxocyclohexanecarboxylate 

Relevant academic research and scientific papers

Synthesis of L-ascorbic acid derivatives as potential bone remodeling agents taking advantage of the Mitsunobu reaction

The synthesis of ascorbic acid derivatives 7a-d is described. Starting from alkenylacetates 1a-d subjected to a hydrosilylation reaction, the resulting hydroxy chloro silanes 3a-d were obtained in high yield. The latter compounds were reacted with potassium phthalimide followed with hydrazine hydrate to give the amino silanols 5a-d. Ascorbic acid was then alkylated on its 3-hydroxy position to give 7a-d by means of a Mitsunobu reaction.

Synthesis of 3-sila derivatives of L-ascorbic acid via Mitsunobu reaction

Various 3-sila derivatives of L-ascorbic acid were synthesized in satisfactory yields. The ether link was formed by an unusual aspect of the Mitsunobu reaction, without the need of protecting the remaining hydroxy groups.

Tetrahydro-4 H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

This study describes our recent efforts to find an efficient and scalable route to tetrahydro-4H-pyran-4-one using the commercially available starting materials. The route scouting work and the full development of an efficient access to the target are described. This work culminated in the preparation of above 20 kg of the title compound in our pilot plant facility.

Developing a Bench-Scale Green Diboration Reaction toward Industrial Application

We report a new methodology for the organocatalytic diboration reaction using inexpensive, sustainable, nontoxic, commercially available halogen salts. This is an educative manuscript for the transformation of laboratory scale reactions into a sustainable approach of appeal to industry.

Amine Catalysis for the Organocatalytic Diboration of Challenging Alkenes

The generation of in situ sp2–sp3diboron adducts has revolutionised the synthesis of organoboranes. Organocatalytic diboration reactions have represented a milestone in terms of unpredictable reactivity of these adducts. However, current methodologies have limitations in terms of substrate scope, selectivity and functional group tolerance. Here a new methodology based on the use of simple amines as catalyst is reported. This methodology provides a completely selective transformation overcoming current substrate scope and functional/protecting group limitations. Mechanistic studies have been included in this report.

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.

Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand

A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).

Synthesis and glycosidase inhibition studies of 5-methyl-substituted tetrahydroxyindolizidines and -pyrrolizidines related to natural hyacinthacines B

The synthesis of three tetrahydroxyindolizidines and one tetrahydroxypyrrolizidine related to natural hyacinthacines B and their biological evaluation as glycosidase inhibitors is reported. The target molecules were obtained through highly stereoselective cycloadditions between sugriched allylic and homoallylic alcohols. This allowed the installation of a methyl group at C5 - a common feature of many natural hyacinthacines - with high control over the stereoselectivity. The new compounds inhibit amyloglucosidase from Aspergillus niger and β-glucosidase from almonds. Compound 1 is a competitive inhibitor of amyloglucosidase and shows a fair selectivity towards this enzyme. The presence of C5-Me substitution in indolizidines 2 and 3 slightly diminishes the inhibitory activity towards amyloglucosidase whereas it improves the inhibitory properties towards β-glucosidase. Cycloaddition between a carbohydrate-derived nitrone and suitable chemoenzymatically prepared enantioenriched allylic and homoallylic alcohols allowed the straightforward synthesis of three tetrahydroxyindolizidines and one tetrahydroxypyrrolizidine related to natural hyacinthacines B. They inhibit amyloglucosidase from Aspergillus niger and β-glucosidase from almonds. Copyright

Hydroacetoxylation of olefins with acetic acid genetated in situ from vinyl acetate in the presence of ruthenium complexes

Ruthenium complexes catalyze the decomposition of vinyl acetate releasing the acetic acid and its subsequent addition to linear and cyclic olefins.

Esterification of carboxylate-based ionic liquids with alkyl halides

A facile reaction of 1-ethyl-3-methylimidazolium acetate ([EMIm]Ac) with dichloromethane at room temperature was observed with esters among the products. This esterification can be exploited for mild solvent-free esterification with a range of other carboxylate-based ionic liquids and alkyl halides. The Royal Society of Chemistry.