134268-41-0

Upstream product

• 134268-51-2 phenyl[2-(phenylmethoxy)phenyl]methanone hydrazone 
• 25187-00-2 2-iodobenzophenone 
• 221458-86-2 (phenyl)[2-(2-phenylethynyl)phenyl]methanone 
• 67-56-1 methanol 
• 134268-37-4 2-benzyloxyphenyl(phenyl)diazomethane 
• 110-82-7 cyclohexane 
• 41570-67-6 1-benzyltetrahydro-1H-thiophen-1-ium bromide 
• 134268-50-1 2-isopropoxybenzophenone hydrazone 
• 133745-29-6 (2-isopropoxyphenyl)(phenyl)methanone 
• 100-39-0 benzyl bromide 
• 93254-81-0 o-(benzyloxy)benzophenone 
• 117-99-7 2-Hydroxybenzophenone 
• 573974-72-8 2'-benzyloxybenzophenone tosylhydrazone 

Relevant academic research and scientific papers

Regio- and Diastereoselective Organo-Zinc-Promoted Arylation of trans-2,3-Diaryloxiranes by Arylboronic Acids: Stereoselective Access to trans-2,3-Diphenyl-2,3-dihydrobenzofuran

ortho-Oxo substituted trans 2,3-diaryloxiranes were regio- and stereoselectively arylated by arylzinc reagents, obtained from the corresponding boronic acids by B–Zn exchange. The reaction was quite general, irrespective to the aryl nucleophile and proceeded via a ring opening at the α-carbon with respect to the substituted aryl ring. The stereoselectivity was from high to complete toward the alcohol resulted from retention of configuration at the electrophilic carbon. The method allowed a direct and high yielding access to trans 2,3-diphenyl-2,3-dihydrobenzofuran, which is a key structural motif in resveratrol dimers as viniferins. The use of enantioenriched starting diaryloxiranes resulted in no loss of stereochemical integrity in the final trans 2,3-dihydrobenzofuran, which was characterized for the first time in enantioenriched form.

Natural product inspired library synthesis - Identification of 2,3-diarylbenzofuran and 2,3-dihydrobenzofuran based inhibitors of Chlamydia trachomatis

A natural product inspired library was synthesized based on 2,3-diarylbenzofuran and 2,3-diaryl-2,3-dihydrobenzofuran scaffolds. The library of forty-eight compounds was prepared by utilizing Pd-catalyzed one-pot multicomponent reactions and ruthenium-catalyzed intramolecular carbenoid C-H insertions. The compounds were evaluated for antibacterial activity in a panel of test systems including phenotypic, biochemical and image-based screening assays. We identified several potent inhibitors that block intracellular replication of pathogenic Chlamydia trachomatis with IC50 ≤ 3 μM. These new C. trachomatis inhibitors can serve as starting points for the development of specific treatments that reduces the global burden of C. trachomatis infections.

Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids

The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diaste

Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles

(Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [Ru II(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D 4-Por*)(CO)] as catalyst, and up to 96% ee is attained.

Generation and Reactions of 2-Alkoxydiphenylcarbenes in Fluid Solution and Rigid Matrices

Irradiation of 2-alkoxydiphenyldiazomethanes 1 in cyclohexane at room temperature produced 3-phenyldihydrobenzofurans 3 presumably as a result of intramolecular C-H insertion of 2-alkoxydiphenylcarbenes 2.Irradiation of compounds 1 in cyclohexane matrix at -196 deg C gave intermolecular C-H insertion products 4 at the expense of benzofurans 3.The formation of products 4 is explicable in terms of H-atom tunnelling to the triplet state of carbenes 2, followed by coupling of the resulting radical pairs.Product ratios 3:4 were somewhat sensitive to the bulk of the alkoxy group at the 2-position.This can be explained in terms of the matrix effect on the relative population of the rotational isomers of the carbene 2.Irradiation of compounds 1 in methanol at room temperature afforded O-H insertion products 5 almost exclusively, whereas irradiation in methanol matrix at -196 deg C gave C-H insertion products 6 along with other products 3 and 5.