54340-72-6

Usage

Uses

Used in the Food and Beverage Industry:
2-Heptenoic acid, ethyl ester, (2E)is used as a flavoring agent for its fruity, floral scent, enhancing the taste and aroma of various food and beverage products.
Used in the Perfume and Fragrance Industry:
2-Heptenoic acid, ethyl ester, (2E)is utilized as a key ingredient in perfumes and fragrances due to its appealing aroma, contributing to the creation of unique and attractive scents.
Used in Organic Synthesis:
2-Heptenoic acid, ethyl ester, (2E)has potential applications in organic synthesis, where it can serve as a building block or intermediate in the production of other organic compounds.
Used in the Cosmetic Industry:
It is employed as a solubilizer in cosmetic products, helping to dissolve and stabilize other ingredients, thereby improving the texture, consistency, and performance of the final product.

InChI:InChI=1/C9H16O2/c1-3-5-6-7-8-9(10)11-4-2/h7-8H,3-6H2,1-2H3/b8-7+

Upstream product

• 16930-95-3 ethyl hept-2-ynoate 
• 109-72-8 n-butyllithium 
• 623-47-2 propynoic acid ethyl ester 
• 693-03-8 n-butyl magnesium bromide 
• 117659-25-3 ethyl (E)-3-[(4-methylphenyl)sulfonyl]-2-propenoate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 110-62-3 pentanal 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 71-41-0 pentan-1-ol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 1071-46-1 hydrogen ethyl malonate 
• 1026993-42-9 3-acetoxy-1-ethoxy-1-heptyne 
• 2678-54-8 ketene diethyl acetal 

Downstream Products

• 1577-31-7 (Z)-hept-2-enoic acid 
• 129397-20-2 (2S,3R)-3-Butyl-2-dibenzylamino-pentanedioic acid 1-tert-butyl ester 5-ethyl ester 
• 33467-76-4 (E)-hept-2-en-1-ol 
• 79918-79-9 ethyl (Z)-hept-3-enoate 
• 54340-71-5 (E)-ethyl hept-3-enoate 
• 139618-55-6 Ethyl trans-3-butyloxirane-2-carboxylate 
• 1329675-12-8 (2S,4Z)-4-{[(tert-butyl)diphenylsilyl]oxy}oct-2-enal 
• 1401904-87-7 (tert-butyl){[(1S,2Z)-1-butyl-3-(oxiran-2-yl)prop-2-en-1-yl]oxy}diphenylsilane 
• 1401904-89-9 (tert-butyl){[(1S,2Z)-1-butyl-3-[(2S)-oxiran-2-yl]prop-2-en-1-yl]oxy}diphenylsilane 
• 1401904-92-4 ethyl (5R,6Z,8S)-8-{[(tert-Butyl)diphenylsilyl]oxy}-5-hydroxydodec-6-en-2-ynoate 
• 1401904-95-7 ethyl (2Z,5R,6Z,8S)-8-{[(tert-butyl)diphenylsilyl]oxy}-5-hydroxydodeca-2,6-dienoate 
• 1401904-98-0 (6R)-6-{(1Z,3S)-3-{[(tert-butyl)diphenylsilyl]oxy}hept-1-en-1-yl}-5,6-dihydro-2H-pyran-2-one 
• 1401905-05-2 C₂₃H₃₀OSi 
• 1329675-11-7 (4S)-4-{[(tert-butyl)diphenylsilyl]oxy}oct-2-ynal 

Relevant academic research and scientific papers

Stereoselective synthesis of (+)-boronolide

An efficient enantio- and stereocontrolled total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric dihydroxylation, a chelation controlled Grignard reaction followed by Sharpless asymmetric epoxidati

STEREOSELECTIVE SYNTHESIS OF (E)-β-ALKYL ACRYLATES AND ACRYLAMIDES

β-Tosyl-α,β-unsaturated esters and amides react regio and stereoselectively with carbanionic reagents to afford β-alkyl, alkenyl, or alkynyl substituted α,β-enoates or enamides with an E configuration.

Enantio- and diastereocontrolled total synthesis of (+)-boronolide

An efficient stereoselective total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric hydroxylation, a chelation-controlled vinyl Grignard reaction followed by a Sharpless asymmetric epoxidation, hydr

Copper-Catalyzed Azide–Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles

Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asymmetric azide–ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asymmetric azide–alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theoretical calculations.

Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes

The visible-light-promoted diastereodivergent intramolecular oxyamination of alkenes is described to construct oxazolindinones, pyrrolidinones and imidazolidones via mild generation of primary amidyl radicals from functionalized hydroxylamines. A unique phenomenon of highly diastereoselective ring-opening of aziridines controlled by electron sacrifices was observed. Highly diastereoselective amino alcohols derivatives were obtained efficiently through this protocol in gram scales. The mechanistic studies suggested the isolatable anti-aziridine intermediates were generated quickly from primary amidyl radicals and the diastereoselectivities were controlled by pKavalues of the electron sacrifices.

Total synthesis of umuravumbolide

A simple and efficient stereoselective total synthesis of (+)-umuravumbolide (1b) and (-)-deacetylumuravumbolide (1a) starting from commercially available pentanal is described. The synthesis involves Sharpless asymmetric epoxidation, Jacobsen's hydrolytic kinetic resolution (HKR), and the Yamaguchi oxirane opening as key steps (Scheme2).

A two-step ball milling method synthesizes and purifies α,β-unsaturated esters

Over the last decade, solvent-free methods have been gaining interest as replacements for traditional organic chemistry techniques. While solvent-free methods are well known for many processes, a simple, solvent-free purification procedure that supplements them does not exist. We report the solvent-free synthesis of α,β-unsaturated esters using a solvent-free Horner-Wadsworth-Emmons (HWE) reaction using high-speed ball milling (HSBM). We were able to perform the HWE reaction on a variety of aldehydes, and isolate their respective a,b-unsaturated esters in high yields, purities, and diastereoselectivities. The Royal Society of Chemistry.

Towards the catalytic formation of α,β-vinylesters and alkoxy substituted γ-lactones

A facile, one pot, high yield synthesis of α,β-vinylester (1-14) and alkoxy substituted γ-lactones (15-28) has been achieved by the photochemical reaction of terminal acetylene (ferrocenyl phenyl trimethylsillyl, hexyl and cyclohexyl) with alcohol (methanol, ethanol and isopropanol) and carbon monoxide in presence of iron pentacarbonyl as a catalyst. The selectivity of the compounds depends on the time of photolysis of the reaction as well as the solvent used. A stable reaction intermediate ferrole was isolated, and further photolysis with alcohols, resulted in the formation of α,β-vinylester. All the compounds were fully characterised by spectroscopic methods and the molecular structures of compounds 1, 16, 17 and 20 were established crystallographically.

Catalytic synthesis of (E)-a,β-unsaturated esters from aldehydes and 1,1-diethoxyethylene

A practical and high yielding synthesis of a,β-unsaturated esters from aldehydes and 1,1-diethoxyethylene was developed.

A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main compounds of interest involved are given, together with their CD spectra.