7468-58-8

Upstream product

• 2107-70-2 3,4-methoxycinnamic acid 
• 591-51-5 phenyllithium 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 4249-72-3 2-phenoxy-1-phenylethanol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 53744-27-7 3,4-dimethoxychalcone 
• 53744-27-7 3,4-dimethoxychalcone 

Downstream Products

• 101596-81-0 5,6-dimethoxy-3-phenyl-1H-indene 
• 41868-64-8 7,8-dimethoxy-3a-phenyl-(3ar,9bc)-2,3,3a,4,5,9b-hexahydro-naphtho[2,1-d]oxazole 
• 41868-55-7 2c-amino-6,7-dimethoxy-2t-phenyl-1,2,3,4-tetrahydro-naphthalen-1r-ol 

Relevant academic research and scientific papers

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.

Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination

A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.

Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.

Targeted Covalent Inhibition of Plasmodium FK506 Binding Protein 35

FK506-binding protein 35, FKBP35, has been implicated as an essential malarial enzyme. Rapamycin and FK506 exhibit antiplasmodium activity in cultured parasites. However, due to the highly conserved nature of the binding pockets of FKBPs and the immunosuppressive properties of these drugs, there is a need for compounds that selectively inhibit FKBP35 and lack the undesired side effects. In contrast to human FKBPs, FKBP35 contains a cysteine, C106, adjacent to the rapamycin binding pocket, providing an opportunity to develop targeted covalent inhibitors of Plasmodium FKBP35. Here, we synthesize inhibitors of FKBP35, show that they directly bind FKBP35 in a model cellular setting, selectively covalently modify C106, and exhibit antiplasmodium activity in blood-stage cultured parasites.

Efficient Organoruthenium Catalysts for α-Alkylation of Ketones and Amide with Alcohols: Synthesis of Quinolines via Hydrogen Borrowing Strategy and their Mechanistic Studies

A new family of phosphine free organometallic ruthenium(II) catalysts (Ru1–Ru4) supported by bidentate NN Schiff base ligands (L1–L4 where L1=N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazineylidene)methyl) aniline, L2=N,N-diethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazineylidene)methyl)aniline, L3=N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-yl)hydrazineylidene)methyl)- aniline and L4=N,N-diethyl-4-((2-phenyl-2-(pyridin-2-yl)hydrazineylidene)methyl) aniline) was prepared and characterized. These half-sandwich complexes acted as catalysts for C?C bond formation and exhibited excellent performance in the dehydrogenative coupling of ketones and amides. In the synthesis of C–C bonds, alcohols were utilized as the alkylating agent. A broad range of substrates, including sterically hindered ketones and alcohols, were well tolerated under the optimized conditions (TON up to 47000 and TOF up to 11750 h?1). This ruthenium (II) catalysts were also active towards the dehydrogenative cyclization of o-amino benzyl alcohol for the formation of quinolines derivatives. Various polysubstituted quinolines were synthesized in moderate to excellent yields (TON up to 71000 and TOF up to 11830 h?1). Control experiments were carried out and the ruthenium hydride intermediate was characterized to support the reaction mechanism and a probable reaction pathway of dehydrogenative coupling for the C?C bond formation has been proposed.

Method for synthesizing alpha-alkylated ketone in water

The invention discloses a method for synthesizing alpha-alkylated ketone in water. The method comprises the following steps: adding ketone, compound alcohol, a transition metal iridium catalyst, an alkali and a solvent, namely water into a reaction container, carrying out a reflux reaction on a reaction mixture in the air for several hours, carrying out cooling to room temperature, carrying out rotary evaporation to remove the solvent, and carrying out column separation (ethyl acetate/petroleum ether) to obtain a target compound, namely alpha-alkylated ketone. A reaction equivalent substrate is used in the reaction process, so raw material waste is avoided; equivalent alkali is used, so better environmental protection performance is obtained; water reflux reaction conditions are milder; and non-toxic and harmless pure water is used as the solvent in the reaction, only water is generated as a by-product, so atom reaction economy is high, and the requirements of green chemistry are met.

The α-alkylation of ketones with alcohols in pure water catalyzed by a water-soluble Cp?Ir complex bearing a functional ligand

A water-soluble dinuclear Cp?Ir complex bearing 4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine as a bridging ligand was found to be a highly effective catalyst for the α-alkylation of ketones with alcohols in pure water. In the presence of catalyst (0.5 mol%), a series of desirable products were obtained with high reaction economy under environmentally benign conditions. The importance of the hydroxy group in the ligand for catalytic hydrogen transfer was confirmed by mechanism experiments. Furthermore, the application of this catalytic system for the synthesis of a biologically active molecule donepezil in pure water has been accomplished. Notably, this research would facilitate the progress of C-C bond-forming reactions in water catalyzed by water-soluble metal-ligand bifunctional catalysts.

Ruthenium-Catalyzed β-Alkylation of Secondary Alcohols and α-Alkylation of Ketones via Borrowing Hydrogen: Dramatic Influence of the Pendant N-Heterocycle

Three bidentate ruthenium(II) complexes with a pyridonate fragment were prepared and fully characterized. These complexes are structurally similar, but differ in their pendant substituents. Complex 1 contains a phenyl unit, whereas complexes 2 and 3 have uncoordinated thienyl and thiazolyl groups, respectively. These complexes were tested as catalysts for β-alkylation of secondary alcohols with primary alcohols, and 3 shows the highest activity, suggesting the thiazolyl ring participates in the catalytic process. Furthermore, 3 is an excellent catalyst for α-alkylation of ketones with primary alcohols. Various α-alkylated ketones were synthesized in high yields, by using 0.05 mol % 3 and 0.25 equiv of t-BuOK within 30 min.

Methanol as hydrogen source: Chemoselective transfer hydrogenation of α,β-unsaturated ketones with a rhodacycle

Methanol is a safe, economic and easy-to-handle hydrogen source. It has rarely been used in transfer hydrogenation reactions, however. We herein report that a cyclometalated rhodium complex, rhodacycle, catalyzes highly chemoselective hydrogenation of α,β-unsaturated ketones with methanol as the hydrogen source. A wide variety of chalcones, styryl methyl ketones and vinyl methyl ketones, including sterically demanding ones, were reduced to the saturated ketones in refluxing methanol in a short reaction time, with no need for inter gas protection, and no reduction of the carbonyl moieties was observed. The catalysis described provides a practically easy and operationally safe method for the reduction of olefinic bonds in α,β-unsaturated ketone compounds.

[Pd]-Catalyzed Intermolecular Coupling and Acid Mediated Intramolecular Cyclodehydration: One-Pot Synthesis of Indenes

An efficient one-pot synthesis of indenes from simple starting materials is presented. This process involves a dual C–C bond formation through an intermolecular Heck coupling reaction followed by acid-mediated intramolecular cyclodehydration. The strategy