1745-17-1

Usage

Uses

Used in the Food and Beverage Industry:
6-Heptenoic acid methyl ester is used as a flavoring agent for enhancing the taste and aroma of food and beverages, providing a fruity note that is well-received by consumers.
Used in the Perfume Industry:
In the production of perfumes, 6-Heptenoic acid methyl ester serves as a fragrance ingredient, contributing to the creation of complex and pleasant scents that are used in various perfume formulations.
Used in Personal Care Products:
6-Heptenoic acid methyl ester is utilized as a fragrance ingredient in personal care products, such as soaps, lotions, and shampoos, to impart a refreshing and fruity scent that enhances the sensory experience of these products.
Used in the Pharmaceutical Industry:
6-Heptenoic acid methyl ester has potential applications in drug synthesis within the pharmaceutical industry, where its unique chemical properties may be leveraged for the development of new medications.
Overall, the diverse applications of 6-Heptenoic acid methyl ester are driven by its attractive fruity aroma, making it a valuable component in the creation of consumer goods across different sectors.

Upstream product

• 56909-02-5 methyl hept-6-ynoate 
• 186581-53-3 diazomethane 
• 66241-84-7 7-Phenylselanyl-heptanoic acid 
• 67-56-1 methanol 
• 1119-60-4 hept-6-enoic acid 
• 6654-36-0 methyl 6-oxohexanoate 
• 23895-60-5 tri-n-butylstannyldibromomethane 
• 3946-32-5 suberic acid monomethyl ester 
• 82302-70-3 8-oxo-4Z-octenoic acid methyl ester 
• 74785-92-5 methyl 7-phenylselenylheptanoate 
• 196494-62-9 2-Phenylsulfanyl-hept-6-enoic acid methyl ester 
• 2777-58-4 methyl petroselinate 
• 74-85-1 ethene 
• 30515-28-7 7-bromoheptanoic acid 

Downstream Products

• 101254-69-7 8-benzylsulfanyl-6-chloro-octanoic acid methyl ester 
• 41138-69-6 7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester 
• 144190-30-7 2,3-Di-pent-4-enyl-succinic acid dimethyl ester 
• 176101-43-2 2-Benzyl-hept-6-enoic acid methyl ester 
• 1026647-45-9 7-[(1R,2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-heptanoic acid methyl ester 
• 251292-82-7 7-{(1R,2R,5S)-5-Acetoxy-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-3-oxo-cyclopentyl}-heptanoic acid methyl ester 
• 251292-81-6 7-{(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-3-hydroxy-cyclopentyl}-heptanoic acid methyl ester 
• 251292-77-0 7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester 
• 251292-80-5 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester 
• 251292-78-1 7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester 
• 3884-92-2 methyl 8-oxooctanoate 
• 1119-60-4 hept-6-enoic acid 

Relevant academic research and scientific papers

Tandem RCM-Pauson-Khand reaction for access to tricycles in one step

Starting from conveniently designed dienynes complexed to cobalt, a tandem RCM-intramolecular Pauson-Khand reaction yields tricyclic compounds. The methodology allows the synthesis of 6,5,5 and 7,5,5 systems.

Scope of the chromium(II)-mediated synthesis of E-alkenylstannanes from aldehydes and Bu3SnCHBr2

The synthesis of E-alkenylstannanes from aldehydes and a mixture of Bu3SnCHBr2, LiI and CrCl2 is described. A mechanism is proposed to account for the alkene geometry in chromium(II)-mediated alkene synthesis which involves stereoselective addition by a gem-dichromium reagent to an aldehyde followed by a stereospecific elimination step.

Chemoselectivity in the Chromium(II)-Mediated Synthesis of E-Alkenylstannanes from Aldehydes and Bu3SnCHBr2

The synthesis of functionalised E-alkenylstannanes from aldehydes and a mixture of Bu3SnCHBr2, LiI and CrCl2 is described.

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

One and Two-Carbon Homologation of Primary and Secondary Alcohols to Corresponding Carboxylic Esters Using β-Carbonyl BT Sulfones as a Common Intermediate

Herein we report the efficient one- and two-carbon homologation of 1° and 2° alcohols to their corresponding homologated esters via the Mitsunobu reaction using β-carbonyl benzothiazole (BT) sulfone intermediates. The one-carbon homologation approach uses standard Mitsunobu C-S bond formation, oxidation and subsequent alkylation, while the two-carbon homologation uses a less common C-C bond forming Mitsunobu reaction. In this latter case, the use of β-BT sulfone bearing esters lowers the pKa sufficiently enough for the substrate to be used as a carbon-based nucleophile and deliver the homologated β-BT sulfone ester, and this superfluous sulfone group can then be cleaved. In this paper we describe several methods for the effective desulfonylation of BT sulfones and have developed methodology for one-pot alkylation-desulfonylation sequences. As such, overall, a one-carbon homologation sequence can be achieved in a two-pot (four step) procedure and the two-carbon homologation in a two-pot (three step) procedure (three-pot; four step when C-acid synthesis is included). This methodology has been applied to a wide variety of functionality (esters, silyl ethers, benzyls, heteroaryls, ketones, olefins and alkynes) and are all tolerated well providing good to very good overall yields. The power of our method was demonstrated in site-selective ingenol C20 allylic alcohol two-carbon homologation.

Enantioselective allylic hydroxylation of w-alkenoic acids and esters by P450 BM3 monooxygenase

Chiral allylic alcohols of w-alkenoic acids and derivatives thereof are highly important building blocks for the synthesis of biologically active compounds. The direct enantioselective C-H oxidation of linear terminal olefins offers the shortest route toward these compounds, but known synthetic methods are limited and suffer from low selectivities. Described herein is an enzymatic approach using the P450 BM3 monooxygenase mutant A74G/L188Q, which catalyzes allylic hydroxylation with high to excellent chemo- and enantioselectivities providing the desirable secondary alcohols.

Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes

The Pt-catalyzed enantioselective diboration of terminal alkenes can be accomplished in an enantioselective fashion in the presence of chiral phosphonite ligands. Optimal procedures and the substrate scope of this transformation are fully investigated. Reaction progress kinetic analysis and kinetic isotope effects suggest that the stereodefining step in the catalytic cycle is olefin migratory insertion into a Pt-B bond. Density functional theory analysis, combined with other experimental data, suggests that the insertion reaction positions platinum at the internal carbon of the substrate. A stereochemical model for this reaction is advanced that is in line both with these features and with the crystal structure of a Pt-ligand complex.

Combination of RCM and the Pauson-Khand reaction: One-step synthesis of tricyclic structures

The combination of ring-closing metathesis (RCM) followed by an intramolecular Pauson-Khand reaction gives direct entry to tricyclic compounds. The RCM was carried out on a hexacarbonylcobalt-complexed alkyne, this complex acting as a protecting group against enyne metathesis. The procedure was studied for dienynes containing heteroatoms and allows the building of [6,5,5] and [7,5,5] tricyclic systems. The feasibility of the process depends strongly on the nature of the substrate. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of unsaturated dibasic acid esters from five-, six-, and seven-membered cycloalkanones

A new route to diesters of symmetrical octene-, decene-, and dodecenedioic acids was proposed. The ratio of the cis/trans-isomers was 1:4. The synthesis involved oxidative splitting of five-, six-, and seven-membered cycloalkanones with hydrogen peroxide into the corresponding ω-alkenoic acids followed by esterification and metathesis over Re2O7/B 2O3-Al2O3-SnMe4.