25234-83-7

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 7396, 1977 DOI: 10.1021/ja00464a070Tetrahedron Letters, 28, p. 2229, 1987 DOI: 10.1016/S0040-4039(00)96087-8

InChI:InChI=1/C7H12O3/c1-5(6(2)8)4-7(9)10-3/h5H,4H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 6628-79-1 3-methyllevulinic acid 
• 186581-53-3 diazomethane 
• 623-43-8 methyl crotonate 
• 108-24-7 acetic anhydride 
• 79-24-3 Nitroethane 
• 623-43-8 crotonic acid methyl ester 
• 82571-41-3 tert-butyl hydrazone of acetaldehyde 
• 75-07-0 acetaldehyde 
• 14920-89-9 2,3-dimethylfuran 
• 143-33-9 sodium cyanide 
• 917-54-4 methyllithium 
• 6622-76-0 methyl (E)-2-methyl-2-butenoate 
• 917-64-6 methyl magnesium iodide 

Relevant academic research and scientific papers

Formation of β-substituted γ-keto esters via zinc carbenoid mediated chain extension

The conversion of β-keto esters into β-methylated γ-keto esters can be achieved through treatment with zinc carbenoids derived from 1,1-diiodoethane. The incorporation of a β-phenyl substituent is also possible through treatment with diiodotoluene. Georg

An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners

A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.

Addition of alkyllithium and Grignard reagents to tetracarbonyliron complexes of α,β-unsaturated esters

Addition of alkyllithium and Grignard reagents to the tetracarbonyliron complexes of methyl acrylate (1) and methyl crotonate (2) leads to the production of 4-ketoesters via acyl transfer from the metal to the β carbon of the α,β-unsaturated ester.

Method for preparing pentazocine intermediate

The invention belongs to the technical field of chemical synthesis, and provides a method for preparing a pentazocine intermediate, which comprises the following steps: by using low-price methyl acetoacetate as a raw material, carrying out methylation, methoxyformylation and removal of one methoxyformyl group, reducing by using a reducing agent, and reacting the reduction product with alkyl sulfonyl chloride to obtain the pentazocine intermediate; generating a compound with a dialkyl sulfonyl group; reacting a compound with dialkyl sulfonyl with phthalimide potassium salt, removing one alkyl sulfonyl, and grafting phthalimide; carrying out dehydrogenation reaction on the phthalimido product under an alkaline condition to generate a vinyl compound, and reacting the vinyl compound with hydrazine hydrate to obtain the pentazocine intermediate. Cheap compounds are used as initial raw materials, the whole route avoids high-pressure and high-temperature dangerous reactions, and industrial production is facilitated.

Naphthochromenones: Organic Bimodal Photocatalysts Engaging in Both Oxidative and Reductive Quenching Processes

Twelve naphthochromenone photocatalysts (PCs) were synthesized on gram scale. They absorb across the UV/Vis range and feature an extremely wide redox window (up to 3.22 eV) that is accessible using simple visible light irradiation sources (CFL or LED). Their excited-state redox potentials, PC*/PC.? (up to 1.65 V) and PC.+/PC* (up to ?1.77 V vs. SCE), are such that these novel PCs can engage in both oxidative and reductive quenching mechanisms with strong thermodynamic requirements. The potential of these bimodal PCs was benchmarked in synthetically relevant photocatalytic processes with extreme thermodynamic requirements. Their ability to efficiently catalyze mechanistically opposite oxidative/reductive photoreactions is a unique feature of these organic photocatalysts, thus representing a decisive advance towards generality, sustainability, and cost efficiency in photocatalysis.

Proline-promoted dehydroxylation of α-ketols

A new single-step proline-potassium acetate promoted reductive dehydroxylation of α-ketols is reported. We introduce the unexplored reactivity of proline and, for the first time, reveal its ability to function as a reducing agent. The developed metal-free and open-flask operation generally results in good yields. Our protocol allows the challenging selective dehydroxylation of hydroxyketones without affecting other functional groups.

Preparation of β-substituted γ-keto esters by the grignard reaction on N-acylpyrazoles

Various γ-keto esters were prepared by either the alcoholysis of N-(4-oxoalkanoyl)pyrazoles or the Grignard replacement of pyrazole moiety of 4-(N-pyrazolyl)-4-oxoalkanoic esters. By using 3-phenyl-ι-menthopyrazole as a chiral auxiliary, β-substituted γ-keto esters were enantioselectively obtained.

Electroreductive acylation of activated olefins using a reactive metal anode

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Study of photochemical addition of acyl radical to electron-deficient olefins

The photochemical addition of acyl radical to electron-deficient olefins is studied. The scope of the reaction, the mechanism, the role that molecular oxygen plays, the influence of steric effects, and the side reaction that take place are discussed. The reaction was carried out using a range of electron-withdrawing substituents (ketones, amides, lactones, nitrile and esters) with good yields of the corresponding photoadduct in all cases.

An efficient and mild entry to 1,4-dicarbonyl compounds via photochemical addition of acyl radical to electron-deficient olefins

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