21565-82-2

Usage

Uses

Used in the Food and Beverage Industry:
4-Pentynoic acid, methyl ester is used as a flavoring agent for its fruity scent, enhancing the taste and aroma of various food and drink products.
Used in the Perfume and Fragrance Industry:
4-Pentynoic acid, methyl ester serves as a key ingredient in the production of perfumes and fragrances, capitalizing on its appealing aroma to create desirable scents for consumer products.
Used in the Pharmaceutical Industry:
4-Pentynoic acid, methyl ester is utilized as an intermediate in the synthesis of a range of pharmaceutical compounds, playing a crucial role in drug development and production.
Used in Organic Synthesis:
As a building block in organic chemistry, 4-Pentynoic acid, methyl ester is employed in the preparation of other organic compounds, contributing to the creation of a diverse array of chemical products.

InChI:InChI=1/C6H8O2/c1-3-4-5-6(7)8-2/h1H,4-5H2,2H3

Upstream product

• 67-56-1 methanol 
• 6089-09-4 4-pentynoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 5390-04-5 pent-1-yn-5-ol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 322399-61-1 10-bromodeca-5,8-diynoic acid methyl ester 
• 209860-36-6 10-hydroxy-deca-5,8-diynoic acid methyl ester 
• 77758-51-1 methyl hex-5-ynoate 
• 90288-79-2 methyl 3-(trimethylsiloxy)-1-cyclopropanecarboxylate 
• 75-36-5 acetyl chloride 
• 17920-23-9 diethyl propargylmalonate 
• 112532-68-0 1-(3-butynyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 

Downstream Products

• 4141-96-2 8-Hydroxy-9-phenyl-nona-4,6-diinsaeure-methylester 
• 109574-14-3 (E)-methyl-5-chloro-4-phenylselenopent-4-enoate 
• 109574-03-0 (E)-4-Chloro-5-phenylsulfanyl-pent-4-enoic acid methyl ester 
• 109574-04-1 methyl-5-chloro-4-phenylthiopent-4-enoate 
• 16387-71-6 deca-4,6-diyne 
• 168331-17-7 deca-4,6-diynoic acid methyl ester 
• 24643-49-0 deca-4,6-diynedioic acid dimethyl ester 
• 268733-86-4 5-[4-(3,3-dimethyl-butoxymethyl)-phenyl]-pent-4-ynoic acid methyl ester 
• 268733-94-4 5-[4-(4,4-dimethyl-pentyloxy)-phenyl]-pent-4-ynoic acid methyl ester 
• 268733-76-2 4-(4-methoxycarbonyl-but-1-ynyl)-benzoic acid 3,3-dimethyl-butyl ester 
• 268733-87-5 5-[4-(1-isopropyl-3,3-dimethyl-butoxymethyl)-phenyl]-pent-4-ynoic acid methyl ester 
• 268733-95-5 5-[4-(2-isopropyl-4,4-dimethyl-pentyloxy)-phenyl]-pent-4-ynoic acid methyl ester 
• 268733-77-3 4-(4-methoxycarbonyl-but-1-ynyl)-benzoic acid 1-isopropyl-3,3-dimethyl-butyl ester 
• 741721-52-8 5-(2,5-difluoro-3-nitro-phenyl)-pent-4-ynoic acid methyl ester 

Relevant academic research and scientific papers

"clickable" SBA-15 mesoporous materials: Synthesis, characterization and their reaction with alkynes

SBA-15 mesoporous silica has been functionalized with azidopropyl groups through both one-pot co-condensation and post-synthetic grafting. For both these methodologies, azidopropyltriethoxysilane was used to introduce the azidopropyl groups. The azidopropyl modified SBA-15 material synthesized by one-pot co-condensation had hexagonal crystallographic order, pore diameters up of 50 A, and the content of azidopropyl groups was found to be 1.3 mmol g -1. The presence of the azidopropyl group was confirmed by multinuclear (13C, 29Si) solid state NMR and IR spectroscopy. Both these materials underwent very efficient Cu(I)-catalyzed azide alkyne "click" reaction (CuAAC) with a variety of alkynes. Nearly 85% of the azide present in the SBA-15 material was converted to the corresponding triazole when propargyl alcohol was used as the substrate. This methodology was also used to incorporate mannose into SBA-15. Incubation of this mannose labeled SBA-15 with fluorescein labeled Concanavalin-A led to the formation of a fluorescent silica-protein hybrid material. The ease of synthesis for the azide labeled SBA-15 material together with its ability to undergo very efficient chemoselective CuAAC in water would make it a very attractive platform for the development of covalently anchored catalysts, enzymes and sensors.

Regioselective [2 + 2 + 2] cycloaddition of a nickel-benzyne complex with 1,3-diynes

(Matrix presented) Reactions of nickel(0)-benzyne complexes with a range of symmetrically substituted 1,3-diynes in the presence of triethylphosphine lead to the regioselective formation of 2,3-dialkynyl naphthalenes. The regioselectivity can be reversed

One-pot generation of c=x bonds from methyl 2-siloxycyclopropanecarboxylates: Simple syntheses of functionalized nitriles and alkynes

Starting from methyl 2-siloxycyclopropanecarboxylates simple and efficient one-pot procedures are described that lead to β-cyanoesters and methoxycarbonyl-substituted terminal alkynes. The prepared functionalized alkynes were subjected to typical transformations such as [3+2] cycloaddition providing triazole derivatives, Sonogashira coupling, Au-catalyzed hydrophosphorylation or a copper-catalyzed coupling of methyl diazoacetate furnishing alkyne 14 and allene derivative 15. The Pauson-Khand reaction of the enyne 4c afforded a diastereomeric mixture of methyl 5-oxohexahydropentalen-2-carboxylate 16 in moderate yield.

AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE

Relating to a compound represented by formula (I) and a pharmaceutically acceptable salt of the compound, and an application of the compound as an S1P1 agonist.

PGDH INHIBITORS AND METHODS OF MAKING AND USING

Disclosed herein are compounds that can inhibit 15-hydroxyprostaglandin dehydrogenase. Such compounds may be administered to subjects that may benefit from modulation of prostaglandin levels.

PDE4 INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND THERAPEUTIC APPLICATIONS

Provided herein are phosphodiesterase 4 (PDE4) inhibitors, e.g., a compound of Formula (I) or (II), and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventing, or ameliorating one or more symptoms of a disease, disorder, or condition associated with PDE4 malfunction.

Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid

The C16-C22 fragment with the acetylene terminus was constructed through the asymmetric dihydroxylation of the corresponding olefin, while the 15-iodo-olefin corresponding to the C11-C15 part was prepared via the asymmetric transfer hydrogenation of the corresponding acetylene ketone followed by hydrozirconation/iodination. Both pieces were joined by a Sonogashira coupling, and the product was further converted into the title compound via a Wittig reaction with the remaining C1-C10 segment and Boland reduction using Zn with TMSCl.

Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling

The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF2α, 6,15-diketo-PGF1α and 6-keto-PGF1α.

Asymmetric Total Synthesis of 19,20-Epoxydocosapentaenoic Acid, a Bioactive Metabolite of Docosahexaenoic Acid

In this study, we report the first asymmetric total synthesis of 19,20-epoxydocosapentaenoic acid (19,20-EDP), a naturally occurring bioactive cytochrome P450 metabolite of docosahexaenoic acid, a major constituent of fish oil. Our strategy involves direct asymmetric epoxidation to produce an enantiopure β-epoxyaldehyde that can be appended to the rest of the skipped polyene core by Wittig condensation. Our route is step-economical and late divergent and could be an appealing method by which to synthesize EDP analogues for biological studies.

Gold-catalyzed Rapid Construction of Nitrogen-containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

1,3-unsubstituted 2-(1H-indol-2-yl)ethanamines were employed for the first time to react with alkynoic acids (AAs) to achieve gold-catalyzed highly selective cascade reactions to furnish novel indole-fused skeletons. Furthermore, with this powerful gold catalytic system, a library of indole/pyrrole/thiophene/benzene/naphthalene/pyridine-based nitrogen-containing heterocyclic compounds (NCHCs) with scaffold diversity and molecular complexity was constructed rapidly using various amine nucleophiles (ANs) and diverse AAs as the building blocks. This general protocol features excellent selectivity, extraordinarily broad substrate scope, readily available inputs, good to high yields, high bond-forming efficiency, and step economy, thus providing a facile and efficient access to a variety of valuable nitrogen-containing heterocycles.