81532-80-1

Upstream product

• 134613-38-0 (Z)-3-Isopropylamino-1-(4-methoxy-phenyl)-but-2-en-1-one 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 768-60-5 4-methoxyphenylacetylen 
• 696-62-8 para-iodoanisole 
• 111887-18-4 4-(4-methoxyphenyl)but-3-yn-2-ol 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 141-78-6 ethyl acetate 
• 108-24-7 acetic anhydride 
• 74-88-4 methyl iodide 

Downstream Products

• 681432-04-2 1-[2-(4-methoxyphenyl)pyrazolo[1,5-b]pyridazin-3-yl]ethanone 
• 913185-54-3 3,4-bis(4-methoxybenzoyl)hex-3-ene-2,5-dione 
• 150444-57-8 (Z)-4-hydroxy-4-(4-methoxyphenyl)-3-buten-2-one 
• 1189116-43-5 1-cyano-2-(4-methoxybenzylidene)-3-oxo-5-phenylcyclopentanecarboxylic acid ethyl ester 
• 1224854-00-5 4-(1-methyl-1-phenylinden-3-yl)phenol 
• 1359849-94-7 C₂₇H₁₉FO₄ 
• 1359850-35-3 C₂₇H₁₉FO₄ 
• 1359849-96-9 C₂₇H₁₉BrO₄ 
• 1359850-36-4 C₂₇H₁₉BrO₄ 
• 1440419-82-8 (R)-6-(4-methoxyphenyl)-2',4-dioxospiro[cyclohex[5]ene-2,3'-indoline]-1,1-dicarbonitrile 
• 1440419-89-5 (R)-5'-fluoro-6-(4-methoxyphenyl)-2',4-dioxospiro[cyclohex[5]ene-2,3'-indoline]-1,1-dicarbonitrile 

Relevant academic research and scientific papers

Cobalt-Catalyzed Chemo- and Enantioselective Hydrogenation of Conjugated Enynes

Asymmetric hydrogenation is one of the most powerful methods for the preparation of single enantiomer compounds. However, the chemo- and enantioselective hydrogenation of the relatively inert unsaturated group in substrates possessing multiple unsaturated bonds remains a challenge. We herein report a protocol for the highly chemo- and enantioselective hydrogenation of conjugated enynes while keeping the alkynyl bond intact. Mechanism studies indicate that the accompanying Zn2+ generated from zinc reduction of the CoII complex plays a critical role to initiate a plausible CoI/CoIII catalytic cycle. This approach allows for the highly efficient generation of chiral propargylamines (up to 99.9 % ee and 2000 S/C) and further useful chemical transformations.

Synthesis of substituted benzo[: B] [1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 °C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by using this synthetic protocol. Mechanistic experiments indicated that the hydroxy proton of the aminophenol could play a crucial role in the formation of an alkynylketimine intermediate that undergoes 7-endo-dig cyclization.

Lewis-base-catalysed selective reductions of ynones with a mild hydride donor

Ynones are efficiently reduced with a mild hydride donor in the presence of a catalytic amount of nucleophilic phosphines. The reactions are selective 1,2-reductions that give propargyl alcohols in yields of up to 96%. It is proposed that success in these reactions depends on the activation of ynones by a Lewis base catalyst. A protic additive plays a key role in suppressing the undesired reaction pathways and accelerating the 1,2-reductions.

Enantioselective Cyanosilylation of Alkynyl Ketones Catalyzed by Combined Systems Consisting of Chiral Ruthenium(II) Complex and Lithium Phenoxide

Asymmetric cyanosilylation of alkynyl ketones with the catalyst systems consisting of amino acid/2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP)/ruthenium(II) complex and lithium phenoxide (Ru?Li cat.) was studied. The reaction was conducted in tert-butyl methyl ether (TBME) at ?78 °C with a substrate-to-catalyst molar ratio (S/C) as high as 2000. A series of simple and functionalized ketones was converted into the alkynyl tertiary cyanohydrin derivatives in up to 99% ee. Appropriate selection of an amino-acid ligand of the catalyst according to the substrate structure was crucially important to achieve high enantioselectivity and a wide scope of substrates. Transformation of the chiral cyanohydrin product into a functionalized lactone was also examined. (Figure presented.).

Gold-catalyzed N,O-functionalization of 1,4-diyn-3-ols with: N -hydroxyanilines to form highly functionalized pyrrole derivatives

This work describes new N,O-functionalization of 1,4-diyn-3-ols with N-hydroxyanilines to yield highly functionalized pyrrole derivatives. In a postulated mechanism, N-hydroxyaniline attacks the more electron-rich alkynes via regioselective N-attack to form unstable ketone-derived nitrones that react with their tethered alkynes via an intramolecular oxygen-transfer to form α-oxo gold carbenes. This new method is applicable to a short synthesis of a bioactive molecule, a PDE4 inhibitor.

Iridium-Catalyzed Asymmetric Transfer Hydrogenation of Alkynyl Ketones Using Sodium Formate and Ethanol as Hydrogen Sources

A green and efficient iridium-catalyzed asymmetric transfer hydrogenation of alkynyl ketones to chiral propargylic alcohols has been developed. By using sodium formate and ethanol as hydrogen sources, a series of alkynyl ketones were hydrogenated by chira

Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions

Salicylic acids and substituted ynones were employed as substrates to afford a class of valuable 4H-benzo[d][1,3]dioxin-4-ones with a 2-site quaternary carbon structure in up to 92% yield by secondary amine-catalyzed dual Michael cascade reactions under mild reaction conditions. The α,β-unsaturated ketone as the key intermediate in the cascade process was successfully separated and characterized. As a result, a new reaction route for ynone species is demonstrated, which is totally different from the existing allenamine activation model.

Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones: Via dual α′,α′-C(sp3)-H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones

A bisphosphine-catalyzed sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones has been developed. Under the catalysis of DPPB [1,4-bis(diphenylphosphino)butane], the reaction proceeded smoothly to give spiro-[cyclopentanone] pyrazolone derivatives in moderate to good yields with good diastereoselectivities via sequential dual α′,α′-C(sp3)-H bifunctionalization annulation. This strategy provides a novel route toward the synthesis of spiro-[cyclopentanone] pyrazolones containing three contiguous stereocenters which possess potential pharmaceutical activities.

A practical synthesis of benzothiophenes via visible-light-promoted cyclization of disulfides and alkynes

Visible-light-promoted intermolecular radical cyclization of disulfides and alkynes has been developed. Benzothiophenes bearing ester, ketone, aldehyde and aryl substituents were synthesized in good yields. The reaction was carried out in the absence of t

Phosphane-Catalyzed [3+3] Annulation of C,N-Cyclic Azomethine Imines with Ynones: A Practical Method for Tricyclic Dinitrogen-Fused Heterocycles

A phosphane-catalyzed [3+3] annulation of azomethine imines with ynones has been developed. Under mild reaction conditions, the reaction proceeds smoothly to afford tricyclic dinitrogen-fused heterocyclic compounds in moderate to excellent yields with moderate to excellent stereoselectivies. Using a chiral phosphine as the catalyst, the reaction could work to give the cycloadduct in moderate yield with moderate enantioselectivity. (Figure presented.) .