60755-22-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 6541, 1989 DOI: 10.1016/S0040-4039(01)89016-X

Upstream product

• 40240-72-0 (E)-1-(4-methoxyphenyl)-4-phenylbut-2-ene-1,4- dione 
• 7448-86-4 1-(4-methoxyphenyl)prop-2-en-1-one 
• 100-52-7 benzaldehyde 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 120312-64-3 C₁₅H₁₄IO₂⁽¹⁺⁾*BF₄^(1-) 
• 60112-44-9 5-(4-methoxyphenyl)furan-2(3H)-one 
• 71-43-2 benzene 
• 201230-82-2 carbon monoxide 
• 17763-67-6 Phenyl triflate 
• 60068-19-1 1-(trimethylsilyloxy)1-(4-methoxyphenyl)cyclopropane 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 120312-58-5 C₁₄H₁₂IO⁽¹⁺⁾*BF₄^(1-) 
• 583-06-2 3-benzoylacrylic acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 59086-11-2 2-(4-methoxyphenyl)-5-phenylthiophene 
• 376637-23-9 1-(4-bromophenyl)-2-(4-methoxyphenyl)-5-phenyl-1H-pyrrole 
• 905971-56-4 C₁₉H₁₇NO₃ 
• 13712-74-8 2-(4-methoxyphenyl)-5-phenyl-1H-pyrrole 
• 94540-81-5 2-(4-methoxyphenyl)-5-phenylfuran 

Relevant academic research and scientific papers

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.

Synthesis of 1,4-Dicarbonyl Compounds by Visible-Light-Mediated Cross-Coupling Reactions of α-Chlorocarbonyls and Enol Acetates

Herein, we report a protocol for visible-light-mediated radical coupling reactions of α-chloroketones and enol acetates to afford 1,4-dicarbonyl compounds, which are important precursors and intermediates in organic synthesis. The reaction involves photoredox-catalyzed activation of the α-chloroketone upon photoelectron transfer, carbon–chlorine bond cleavage, and coupling of the resulting radical with the carbon–carbon double bond of the enol acetate. This mild protocol has a wide substrate scope and moderate to good yields. (Figure presented.).

Proton-Coupled Electron Transfer: Transition-Metal-Free Selective Reduction of Chalcones and Alkynes Using Xanthate/Formic Acid

Highly chemoselective reduction of α,β-unsaturated ketones to saturated ketones and stereoselective reduction of alkynes to (E)-alkenes has been developed under a transition-metal-free condition using a xanthate/formic acid mixture through proton-coupled electron transfer (PCET). Mechanistic experiments and DFT calculations support the possibility of a concerted proton electron-transfer (CPET) pathway. This Birch-type reduction demonstrates that a small nucleophilic organic molecule can be used as a single electron-transfer (SET) reducing agent with a proper proton source.

A method of synthesizing chiral alkene propyl alcohol

The invention discloses a method for synthesizing chiral alkene propyl alcohol method, which belongs to the technical field of organic chemistry. The method adopts the [...] derived binaphthol potassium salt as a chiral [...] catalyst, catalytic [...] pro

Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies

The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Br?nsted base catalysts were described in the study. A number of chiral BINOL derivatives-based alkoxides were synthesized, and their structure-enantioselectivity correlation study in asymmetric isomerization identified a promising chiral Br?nsted base catalyst, which afforded various chiral secondary allylic alcohols (ee up to 99%, S factor up to >200). In the mechanistic study, alkoxide species were identified as active species and the phenol group of BINOL largely affected the high reactivity and enantioselectivity via hydrogen bonding between the chiral Br?nsted base catalyst and substrates. The strategy is the first successful synthesis strategy of various chiral secondary allylic alcohols through enantioselective transition-metal-free base-catalyzed isomerization. The applicability of the strategy had been demonstrated by the synthesis of the bioactive natural product (+)-veraguensin.

Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones

Due to their closely matched reactivity, the coupling of two dissimilar ketone enolates to form a 1,4-diketone remains a challenge in organic synthesis. We herein report that umpolung of a ketone trimethylsilyl enol ether (1 equiv) to form a discrete enol

Detrifluoroacetylation Reaction of Trifluoromethyl-β-diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4-Diketones

Currently, a great deal of research efforts are focused on C–C bond activation for development of novel synthetic methodology. In this paper, a detrifluoroacetylation of trifluoromethyl-β-diketones is described, which allows for the synthesis of succinimides and 1,4-diketones through cascade Michael addition/retro-Claisen reaction and nucleophilic substitution/retro-Claisen reaction. The readily available trifluoromethyl-β-diketones, wide substrate scope, and mild conditions make this method very practical.

Synthesis and 2D-QSAR studies of neolignan-based diaryl-tetrahydrofuran and -furan analogues with remarkable activity against Trypanosoma cruzi and assessment of the trypanothione reductase activity

Two series of diaryl-tetrahydrofuran and -furan were synthesised and screened for anti-trypanosomal activity against trypomastigote and amastigote forms of Trypanosoma cruzi, the causative agent of Chagas disease. Based on evidence that modification of a natural product may result in a more effective drug than the natural product itself, and using known neolignan inhibitors veraguensin 1 and grandisin 2 as templates to synthesise simpler analogues, remarkable anti-trypanosomal activity and selectivity were found for 3,5-dimethoxylated diaryl-furan 5c and 2,4-dimethoxylated diaryl-tetrahydrofuran 4e analogues with EC50 0.01 μM and EC50 0.75 μM, respectively, the former being 260-fold more potent than veraguensin 1 and 150-fold better than benznidazole, the current available drugs for Chagas disease treatment. The ability of the most potent anti-trypanosomal compounds to penetrate LLC-MK2 cells infected with T. cruzi amastigotes parasite was tested, which revealed 4e and 5e analogues as the most effective, causing no damage to mammalian cells. In particular, the majority of the derivatives were non-toxic against mice spleen cells. 2D-QSAR studies show the rigid central core and the position of dimethoxy-aryl substituents dramatically affect the anti-trypanosomal activity. The mode of action of the most active anti-trypanosomal derivatives was investigated by exploring the anti-oxidant functions of Trypanothione reductase (TR). As a result, diarylfuran series displayed the strongest inhibition, highlighting compounds 5d-e (IC50 19.2 and 17.7 μM) and 5f-g (IC50 8.9 and 7.4 μM), respectively, with similar or 2-fold higher than the reference inhibitor clomipramine (IC50 15.2 μM).

Synthesis method of asymmetric diaryl substituted butanedione compounds

The invention relates to a synthesis method of asymmetric diaryl substituted butanedione compounds disclosed as Formula (III). The method comprises the following steps: in a solvent, carrying out reaction on compounds disclosed as Formula (I) and compounds disclosed as Formula (II) in the presence of a catalyst, a ligand and an acidic compound; and after the reaction finishes, carrying out after-treatment, thereby obtaining the compounds disclosed as Formula (III), wherein R is halogen, C1-C6 alkyl or C1-C6 alkoxy, and X is an alkali metal element. Under the combined selection and synergic actions of the specific catalyst, ligand, acidic compound and solvent, the method can obtain the asymmetric diaryl substituted butanedione compounds at high yield, and has favorable application prospects and industrial production potential in the field of organic chemical synthesis. Besides, the invention also relates to a synthesis method of the raw material compounds disclosed as Formula (I) and researches the optimal synthesis conditions and technical characteristics.

Development of a Palladium-Catalyzed Carbonylative Coupling Strategy to 1,4-Diketones

We report on a three-component palladium-catalyzed coupling strategy for accessing a wide range of 1,4-diketones, which represent important precursors to heterocycles. Our method relies on a carbonylative Heck reaction employing substituted allylic alcohols, aryl iodides, and carbon monoxide. The reaction conditions are mild and do not require high CO pressure, and a wide functional group tolerance is revealed, providing the desired 1,4-diketones in moderate to good yields. Furthermore, the methodology is adaptable to the selective installment of 13C-carbon isotopes at either one or both of the carbonyl positions.