24342-04-9

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-PENTYNOATE is used as a reactant for the preparation of lysophosphatidic acid receptor-1 (LPA1) antagonists. These antagonists exhibit potent activity on human lung fibroblasts, which are cells that play a crucial role in the development and maintenance of lung tissue. By targeting LPA1 receptors, these antagonists have the potential to modulate cellular signaling pathways and provide therapeutic benefits in the treatment of various lung-related conditions, such as fibrosis and cancer.

InChI:InChI=1/C6H8O2/c1-3-4-5-6(7)8-2/h3H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 5963-77-9 pent-2-ynoic acid 
• 110475-21-3 5-ethyl-1,2-dihydro-pyrazol-3-one 
• 505-23-7 1,3 dithiane 
• 234118-17-3 (Z)-3-trifluoromethanesulfonyloxy-pent-2-enoic acid methyl ester 
• 107-00-6 but-1-yne 
• 79-22-1 methyl chloroformate 

Downstream Products

• 50652-79-4 (ZE)-3-methyl-2-pentenoate 
• 6089-09-4 4-pentynoic acid 
• 139964-24-2 methyl 4-ethyl-2-propylimidazole-5-carboxylate 
• 30414-53-0 methyl propanoyl acetate 
• 1404326-12-0 C₁₄H₂₀O₂Si 
• 1404326-14-2 C₁₄H₂₀O₂Si 
• 5963-77-9 pent-2-ynoic acid 

Relevant academic research and scientific papers

Reactions of Carbonyl-Conjugated Alkynes with N-Bromosuccinimide and N-Iodosuccinimide in DMF/H2O and Methanol/Sulfuric Acid: Syntheses of Dihalo Diketones, Dihalo Ketoesters, and Dihalo Acetals

The following terminal, carbonyl-conjugated alkynes were reacted with N- bromosuccinimide (NBS) and N-iodosuccinimide (NIS) in MeOH/H2SO4 to give dibromo and diiodo acetals in the indicated yields: 3-butyn-2-one, 1: NBS (75%), NIS (95%); 1-phenyl-1-propyn-l-one, 2: NBS (90%), NIS (40%); 1-hexyn-3-one, 3: NBS (90%), NIS (70%); methyl propiolate, 4: NBS (20%, not isolated), NIS (95%). 4,4-Dimethyl-l-pentyn-3-one (5) gave only a trace of dibromo acetal and no diiodo acetal; tribromide and tetrabromide were the major products. NBS and NIS reactions required, respectively, 20% and 33 wt % of H2SO4. The reaction was unsuccessful with internal alkynes 4-phenyl-3-butyn-2-one and 3-hexyn-2-one which gave only complex mixtures of products. Alkyne 2 gave a significant yield of acetal-ketal in addition to the dihalo acetals. Both the dibromo acetal- ketal and diiodo acetal-ketal were isolated, but only the former could be hydrolyzed to the dibromo acetal. Internal, carbonyl-conjugated alkynes reacted with NBS and NIS in H2O/DMF (40:60) to give the following products in the indicated yields: 4-phenyl-3-butyn-2-one (6): 1-phenyl-3,3- dibromo-1,3-butanedione (17, 70%), 1-phenyl-3,3-diiodo-1,3-butanedione (21, 95%); 3-hexyn-2-one (7): 3,3-dibromo-2,4-hexanedione (18, 80%), 3,3-diiodo-2,4-hexanedione (22, 95%); methyl 3- phenyl-2-propynoate (8): methyl 2,2-dibromo-3-keto-3-phenylpropanoate (19, 43%), methyl 2,2- diiodo-3-keto-3-phenylpropanoate (23, 95%); methyl 2-pentynoate (9): methyl 2,2-dibromo-3- ketopentanoate (20, 80%), methyl 2,2-diiodo-3-ketopentanoate (24, 95%). All reactions, except for 6 and 8 with NBS, required H2-SO4. The terminal, carbonyl-conjugated alkyne, 3-butyn-2-one, did not give products, possibly because of oxidation of the intermediate aldehyde by NBS and NIS. Mechanisms involving electrophilic attack by halogen on the triple bond and an acid-catalyzed mechanism are discussed.

A Serendipitous Synthesis of Bis-Heterocyclic Spiro 3(2 H)-Furanones

(Z) Enol triflates 6, 11b-d, (E) enol triflate 11e, and phenol triflate 11a, derived from β-keto esters or 2-carboalkoxy phenols, respectively, react with N-Boc 2-lithiopyrrolidine (5a), N-Boc N-methylaminomethyllithium (5b), or 2-lithio-1,3-dithiane (14) to afford 3(2H)-furanones in modest to good yields (38-81%). Product and carbanion reagent studies suggest that the 3(2H)-furanone is formed in a cascade of reactions involving nucleophilic acyl substitution, enolate formation, trifluoromethyl transfer, iminium or sulfenium ion formation, and subsequent ring closure to form the 3(2H)-furanone. The use of 2-lithio-1,3-dithiane affords a cyclic α-keto-S,S,O-orthoester in which the functionality can be selectively manipulated for synthetic applications. (Chemical Equation Presented).

Copper-Catalyzed Domino Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidin-4(10H)-ones using Cyanamide as a Building Block

An efficient and practical copper-catalyzed domino synthesis of benzo[4,5]imidazo[1,2-a]pyrimidin-4(10H)-ones has been developed. The protocol uses N-(2-halophenyl)-3-alkylpropiolamides and cyanamide as the starting materials, inexpensive copper(I) iodide and pipecolinic acid as the catalyst and ligand, and the corresponding products were obtained in moderate to good yields.

Rhodium-catalyzed aryl- and alkylation-oligomerization of alkynoates with organoboron reagents giving salicylates

The reaction of alkynoates with aryl- or alkylboron reagents in the presence of a rhodium/diene catalyst gave high yields of salicylate derivatives with high selectivity, which consist of three or four molecules of the alkynoate and one organic group derived from the organoboron reagents. The Royal Society of Chemistry.

One-pot synthesis of trisubstituted monomethylated benzene-1,3-diols via a Michael addition-Dieckmann cyclization sequence from methyl (E)3-methoxy-4- methoxycarbonylbut-2-enoate anion and methyl alkynoates and its application to the total synthesis of nidulol

The reaction of methyl (E)3-methoxy-4-methoxycarbonylbut-2-enoate (1) with a number of methyl alkynoates under appropriate conditions gave the monomethylated trisubstituted resorcinol derivatives 3 in a regiocontrolled manner, via a Michael addition-Dieckmann cyclization sequence in one pot. The resorcinol 3d, prepared in this manner, was used as the starting material for a three step, highly efficient (54% from 3d) synthesis of the bioactive fungal metabolite nidulol (4). Georg Thieme Verlag Stuttgart.

Pigments of Fungi. Part 38. Synthesis of Austrocorticinic Acid and (S)-(-)-Austrocorticin; Absolute Stereochemistry of Natural Austrocorticin

The absolute configuration of the fungal anthraquinone (+)-austrocorticin 1 is established as (R) by synthesis of its antipode from (S)-(-)-but-3-yn-2-ol via a Diels-Alder reaction involving the highly functionalised, chiral butadiene 6.Similarly, austrocorticinic acid is made available from but-1-yne.

Hypervalent Iodine Oxidation of 5-Substituted and 4,5-Disubstituted Pyrazol-3(2H)-ones: A Facile Synthesis of Methyl-2-alkynoates and Methyl 2,3-alkadienoates

Hypervalent iodine oxidation of various 5-substituted pyrazol-3(2H)-ones (1a-h) with iodobenzene diacetate or iodosobenzene in methanol results in fragmentative loss of molecular dinitrogen to yield methyl 2-alkynoates (2a-h).However, 5-methyl-4-substituted pyrazol-3(2H)-ones (3a-d) under similar conditions yield methyl 2,3-allenic esters (4a-d).Methyl 2,3-cycloalkadienoates (6a-e) are obtained by the oxidative cleavage of 4,5-polymethylene pyrazol-3(2H)-ones (5c-e) using iodobenzene diacetate or iodosobenzene in methanol. 5-Methyl-4,4-disubstituted pyrazol-3(2H)-ones (7a-b) were found not to undergo raction under similar conditions.The scope and mechanism of these reactions are discussed.

Hypervalent Iodine Oxidation of 5-Substituted and 5-Methyl-4-substituted Pyrazol-3(2H)-ones. A Facile Synthesis of 2-Alkynoic and 2,3-Allenic Esters

PhI(OAc)2-MeOH causes oxidation of 5-substituted pyrazol-3(2H)-ones to the 2-alkynoic methyl ester and 5-methyl-4-substituted pyrazol-3(2H)-ones to the 2,3-allenic methyl ester.