6270-17-3

Usage

InChI:InChI=1/C12H14O3/c1-2-15-12(14)9-8-11(13)10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

Upstream product

• 4747-13-1 α-methoxystyrene 
• 105-39-5 chloroacetic acid ethyl ester 
• 14308-31-7 2,2-diethoxy-5-phenyl-2,3-dihydro-furan 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 
• 681-94-7 ethyl 2-(tributylstannyl)acetate 
• 32583-34-9 ethyl(trimethylgermyl)acetate 
• 344349-27-5 ethyl 2-(2-propen-1-yloxy)-2-phenylcyclopropanecarboxylate 
• 27374-25-0 [(1-Ethoxycyclopropyl)oxy]trimethylsilane 
• 98-88-4 benzoyl chloride 
• 115205-41-9 (Z)-4-Phenyl-4-phenylsulfanyl-but-3-enoic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 17851-98-8 1-phenyl-1-(tributylstannyloxy)ethene 
• 105-36-2 ethyl bromoacetate 
• 75-03-6 ethyl iodide 

Downstream Products

• 6942-71-8 1-biphenyl-4-yl-4-phenyl-cyclopenta-1,3-diene 
• 101430-17-5 2,3-epoxy-3-phenyl-adipic acid diethyl ester 
• 106379-25-3 (5-oxo-2-phenyl-tetrahydro-[2]furyl)-acetic acid ethyl ester 
• 7144-81-2 1-phenyl-4-p-tolyl-cyclopenta-1,3-diene 
• 83506-38-1 6-phenyl-2-(3'-phenylpyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-one 
• 80109-14-4 1-(4-chloro-phenyl)-4-phenyl-cyclopentadiene 
• 80109-15-5 1-Bromo-4-(4-phenyl-cyclopenta-1,3-dienyl)-benzene 
• 17851-55-7 2-(2-ethoxycarbonylethyl)-2-phenyl-1,3-dioxolane 
• 345292-85-5 2,4-Diphenyl-cyclopenta-1,4-dienecarboxylic acid ethyl ester 
• 80109-09-7 Dimethyl-[4-(4-phenyl-cyclopenta-1,3-dienyl)-phenyl]-amine 
• 80109-10-0 1-Methyl-3-(4-phenyl-cyclopenta-1,3-dienyl)-benzene 
• 17851-38-6 ethyl 4-cyclohexylbutanoate 
• 787-07-5 diethyl 1,4-cyclohexanedione-2,5-dicarboxylate 
• 130906-53-5 (4-ethoxycarbonyl-5-oxo-2-phenyl-cyclopent-1-enyl)-acetic acid 

Relevant academic research and scientific papers

Visible-Light-Induced Multicomponent Synthesis of γ-Amino Esters with Diazo Compounds

A visible-light-induced multicomponent reaction of ethyl diazoacetate, diarylamines, and styrene-type alkenes is described. This novel 1,2-difunctionalization of alkenes can be readily achieved under a simple operation and mild conditions, affording γ-amino esters as major products. The reaction proceeds through the generation of carbon-centered radicals from diazo compounds by a visible-light-promoted proton-coupled electron transfer (PCET) process. The carbon radicals then add to diverse alkenes, delivering new carbon radical species, and the final products are formed with N-centered radicals via a radical-radical coupling.

Synthesis and antimicrobial activity of new 1,2,4-triazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, thiopyrane, thiazolidinone, and azepine derivatives

4-oxo-4-phenylbutanehydrazide 3 was reacted with aryl or alkyl isothiocyanates to give the corresponding N-substituted-2-(4-oxo-4-phenylbutanoyl) hydrazine-1-carbothioamide 4a-c. Cyclization of thiosemicarbazides 4a-c with sodium hydroxide led to the formation of 3-(4-sub-5-thioxo-1,2,4-triazol-3-yl)-propanone 5a-c. Desulfurization of thiosemicarbazides 4a-c by mercuric oxide afforded 3-(5-(sub-amino)-1,3,4-oxadiazol-2-yl)-propanone 6a-c. The reaction of 4a-c with phosphorus oxychloride gave 3-(5-(sub-amino)-1,3,4-thiadiazol-2-yl)-propanone 7a-c. Treatment of 4a-c with ethyl-bromoacetate or α-bromopropionic acid gave N′-(3-sub-thiazolidin-2-ylidene)-butanehydrazide 8a-c and (N′-(3-sub-oxothiazolidin-2-ylidene)-butanehydrazide 9a-c. Chlorination of oxothiazolidine-hydrazide 9a-c by phosphorus oxychloride afforded N-(3-sub-4-oxothiazolidine)-butane-hydrazonoyl-chloride 10a-c. The reaction of 10a-c with mercaptoacetyl-chloride yielded 2-((4-benzoyl-thiopyrane) hydrazono)-3-sub-thiazolidinone 11a-c. Also, reacted of 10a-c with hydrazine hydrate afforded N″-(3-sub-oxothiazolidine)-butane-hydrazon-hydrazide 12a-c. The 3-sub-2-((pyridazine) hydrazono) thiazolidinone 13a-c was obtained by cyclization of 12a-c via refluxing in DMF. The reaction and cyclized of 9a-c with chloroacetyl-chloride in ethanolic KOH afforded 1-((3-sub-4-oxothiazolidine) amino)-azepine-dione 14a-c. The chemical structures of the new compounds have been confirmed by diverse spectroscopy analyses such as IR, NMR, MS, and elemental analysis. The synthesized compounds were tested for their antimicrobial activity and these compounds were considered (Pyridazin-hydrazono-thiazolidinone 13a-c, oxothiazolidin-azepinedione 14a-c, N-thiazolidin-hydrazon-hydrazide 12a-c, and thiopyran-hydrazono-thiazolidinone 11a-c) the most effective as antimicrobial activity.

Visible Light Induced Br?nsted Acid Assisted Pd-Catalyzed Alkyl Heck Reaction of Diazo Compounds and N-Tosylhydrazones

A mild visible light-induced palladium-catalyzed alkyl Heck reaction of diazo compounds and N-tosylhydrazones is reported. A broad range of vinyl arenes and heteroarenes with high functional group tolerance, as well as a range of different diazo compounds, can efficiently undergo this transformation. This method features Br?nsted acid-assisted generation of hybrid palladium C(sp3)-centered radical intermediate, which allowed for new selective C?H functionalization protocol.

Synthesis of new pyrazoles, oxadiazoles, triazoles, pyrrolotriazines, and pyrrolotriazepines as potential cytotoxic agents

4-Oxo-4-phenylbutanehydrazide (1) reacted with many active methylene reagents such as acetylacetone, diethylmalonate, ethylacetoacetate, ethylcyanoacetate, benzoyl-acetonitrile, and malononitrile under neat conditions to afford the corresponding pyrazoles (2–7), also, treatment of butanehydrazide (1) with electrophilic reagents as triethylorthoformate, dimethylformamide-dimethylacetal, acetic anhydride, and carbon disulfide to give 1,3,4-oxadiazoles (8,10,11) and N′-acetyl-butanehydrazide (9). Reacted of butanehydrazide (1) with potassium thiocyanate gave 1,2,4-triazoles (12). Similarly, treatment of (1) with chloroacetamide gave 1,2,4-triazinones (13). The pyrrolotriazinones (14) was obtained by cyclization of (13). Also, butanehydrazide (1) was utilized as a starting material for the synthesized of new Schiff bases as N′-(4-sub-benzylidene)-phenylbutane-hydrazide (15a-c), which are used as an initiative to prepare new compounds such as 1,2,4-triazepinones (16a-c), pyrrolotriazepinones (17a-c), 1,2,4-triazines (18a-c), and pyrrolotriazines (19a-c) by reacted of (15a-c) with each chloroacetamide or formamide. The chemical structure of the newly prepared compounds was determined through the spectrum data, including IR, NMR, and MS. The prepared compounds were tested for their in vitro antitumor activities. The compounds 17a-c, 16a-c, and 19a-c displayed activity against several types of cancer cell lines.

Copper catalyzed C(sp3)-H bond alkylation via photoinduced ligand-to-metal charge transfer

Utilizing catalytic CuCl2 we report the functionalization of numerous feedstock chemicals via the coupling of unactivated C(sp3)-H bonds with electron-deficient olefins. The active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to enable the generation of a chlorine radical which acts as a powerful hydrogen atom transfer reagent capable of abstracting strong electron-rich C(sp3)-H bonds. Of note is that the chlorocuprate catalyst is an exceedingly mild oxidant (0.5 V vs SCE) and that a proposed protodemetalation mechanism offers a broad scope of electron-deficient olefins, offering high diastereoselectivity in the case of endocyclic alkenes. The coupling of chlorine radical generation with Cu reduction through LMCT enables the generation of a highly active HAT reagent in an operationally simple and atom economical protocol.

Palladium/Zinc Co-Catalyzed Asymmetric Hydrogenation of γ-Keto Carboxylic Acids

A palladium-catalyzed asymmetric hydrogenation of levulinic acid has been successful developed by using Zn(OTf)2 as co-catalyst. The present method not only has provided a strategy in the palladium-catalyzed asymmetric hydrogenation of ketone, but also allowed the preparation of a wide range of chiral γ-valerolactones in good yields with excellent enantioselectivities.

Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions

Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.