153644-80-5

Upstream product

• 24165-65-9 1-(3-methoxyphenyl)but-3-en-1-ol 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 1108107-86-3 C₂₂H₂₄O₄ 
• 1087399-25-4 (E)-1-(3-methoxyphenyl)but-2-en-1-one 
• 1453859-77-2 (Z)-1-(3-methoxyphenyl)but-2-en-1-one 
• 1574316-45-2 C₁₁H₁₂N₄O₂ 
• 1574316-69-0 1-(3-methoxyphenyl)but-3-en-1-one oxime 
• 1612790-57-4 (3-methoxyphenyl)(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)methanone 

Relevant academic research and scientific papers

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

Electrochemical Chalcogenation of β,γ-Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

The current report represents a transition-metal-free synthesis of oxazoline and isoxazoline derivatives by a tandem electro-oxidative chalcogenation-cyclization process. Both C?Se and C?S bond-forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline derivatives were synthesized with up to 91% isolated yield. (Figure presented.).

Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant CC Bond Cleavage

A Cu-catalyzed aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant CC bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.

Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent

A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.

Organocatalytic Redox Isomerization of Electron-Deficient Allylic Alcohols: Synthesis of 1,4-Ketoaldehydes

An organocatalytic redox isomerization strategy has been developed for the synthesis of 1,4-ketoaldehydes. DABCO was found to be the best catalyst for the isomerization of -hydroxy enones. With 20 mol % of DABCO as catalyst and DMSO as the solvent high yi

Iodine(III)-Mediated Oxy-fluorination of Alkenyl Oximes: An Easy Path to Monofluoromethyl-Substituted Isoxazolines

A highly regioselective intramolecular oxy-fluorination of alkenyl oximes was achieved. This new transformation represents an efficient method for the preparation of monofluoromethyl-substituted isoxazolines. The synthetic application of the oxy-fluorinat

Copper-catalyzed oxyazidation of unactivated alkenes: A facile synthesis of isoxazolines featuring an azido substituent

A novel and efficient Cu(OAc)2-catalyzed oxyazidation of unactivated alkenes was developed. The reactions are easy to conduct, occur under mild conditions, and form azido-substituted isoxazolines in good yields.

Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones

Developing olefin isomerization reactions to reach kinetically controlled Z-alkenes is challenging because formation of trans-alkenes is thermodynamically favored under the traditional catalytic conditions using acids, bases, or transition metals as the catalysts. A new synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones to α,β-unsaturated ketones was developed, providing an easy and efficient way to access various Z-enones.

Asymmetric hydrocyanation of α,β-unsaturated ketones into β-cyano ketones with the [Ru(phgly)2(binap)]/C6H 5OLi catalyst system

Enantioselective conjugate addition of HCN to α,β-unsaturated ketones catalyzed by the combined system of [Ru{(S)-phgly}2{(S)- binap}] and C6H5OLi has afforded β-cyano ketones in high yield (see scheme). No detectable amount of the corresponding 1,2-adduct was produced and tert-C4H9OCH3 was the solvent of choice. The cyanation was conducted with a substrate-to-catalyst molar ratio in the range of 200:1-1000:1 at -20-0°C. Copyright

Highly efficient chromium-catalyzed oxidation of secondary benzylic alcohols by aqueous 70% tert-butyl hydroperoxide

The oxidation of secondary benzylic alcohols to ketones by the chromium(VI) oxide/tert-butyl hydroperoxide system is compatible with the presence of methyl, halide, methoxy, acetoxy or nitro substituents on the aryl group and of an unsaturation on the alkyl side chain. Benzyl alcohol led to a mixture of benzaldehyde and benzoic acid.