3770-80-7Relevant articles and documents
Synthesis of fluorine-containing prenylated benzophenones
Mzozoyana, Vuyisa,van Heerden, Fanie R.
supporting information, p. 2226 - 2235 (2020/07/09)
In this study, an effective route to synthesize fluorine-containing prenylated benzophenones was developed. Friedel–Crafts acylation and electrophilic aromatic substitution reactions were the key reactions of this synthesis to achieve these fluorinated prenylated benzophenones. The use of DBU in the prenylation step achieved only the C-prenylated benzophenones, whereas K2CO3 produced the C- and O-prenylated benzophenones.
The Natural Product Elegaphenone Potentiates Antibiotic Effects against Pseudomonas aeruginosa
Zhao, Weining,Cross, Ashley R.,Crowe-McAuliffe, Caillan,Weigert-Munoz, Angela,Csatary, Erika E.,Solinski, Amy E.,Krysiak, Joanna,Goldberg, Joanna B.,Wilson, Daniel N.,Medina, Eva,Wuest, William M.,Sieber, Stephan A.
supporting information, p. 8581 - 8584 (2019/05/28)
Natural products represent a rich source of antibiotics that address versatile cellular targets. The deconvolution of their targets via chemical proteomics is often challenged by the introduction of large photocrosslinkers. Here we applied elegaphenone, a largely uncharacterized natural product antibiotic bearing a native benzophenone core scaffold, for affinity-based protein profiling (AfBPP) in Gram-positive and Gram-negative bacteria. This study utilizes the alkynylated natural product scaffold as a probe to uncover intriguing biological interactions with the transcriptional regulator AlgP. Furthermore, proteome profiling of a Pseudomonas aeruginosa AlgP transposon mutant provided unique insights into the mode of action. Elegaphenone enhanced the elimination of intracellular P. aeruginosa in macrophages exposed to sub-inhibitory concentrations of the fluoroquinolone antibiotic norfloxacin.
Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
Liu, Guangchang,Xu, Bo
supporting information, p. 869 - 872 (2018/02/09)
We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
Synthesis of 3-geranyl- and 3-prenyl-2,4,6-trihydroxybenzophenone
Mzozoyana, Vuyisa,van Heerden, Fanie R.
supporting information, p. 599 - 603 (2017/03/15)
Biologically active phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone (2) and phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (3) were synthesized by an efficient and convenient synthetic sequence. The reaction steps of this synthesis included methylation, Friedel-Crafts acylation, demethylation and geranylation steps.
P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
, p. 12337 - 12340 (2017/11/20)
p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction
Vekariya, Rakesh H.,Aubé, Jeffrey
supporting information, p. 3534 - 3537 (2016/08/16)
The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.
Facile formation of methylenebis(chalcone)s through unprecedented methylenation reaction. Application to antiparasitic and natural product synthesis
Thevenin, Marion,Mouray, Elisabeth,Grellier, Philippe,Dubois, Joelle
supporting information, p. 2986 - 2992 (2014/05/20)
The formation of methylenebis(chalcone)s has been discovered during deprotection with methoxymethyl groups from trihydroxychalcones. Studies on this methylenation reaction led to a mechanism hypothesis that was extended to other chalcones and to dihydrochalcone, acetophenone, benzophenone and flavone derivatives. This new method was applied to the rapid synthesis of natural product piperanduncin C. These original methylenebis compounds were also evaluated for their antiparasitic activity. Copyright
Phenyltellanyl triflate (PhTeOTf) as a powerful tellurophilic activator in the friedel-crafts reaction
Yamada, Takeshi,Mishima, Eri,Ueki, Kazuya,Yamago, Shigeru
, p. 650 - 651 (2008/12/20)
A powerful electrophilic activator for organotellurium compounds was developed. Phenyltellanyl triflate (PhTeOTf) prepared in situ from dibromophenyl(phenyltellanyl)telluride and AgOTf selectively activated various organotellurium compounds in the presence of aromatic compounds yielding the corresponding Friedel-Crafts reaction products. Polymer-end organotellurium compounds were also activated by PhTeOTf providing the corresponding end-functionalized polymers. Copyright
A facile phenol-driven intramolecular diastereoselective thermal/base-catalyzed dipolar [2 + 2] annulation reactions: An easy access to complex bioactive natural and unnatural benzopyran congeners
Mondal, Mukulesh,Puranik, Vedavati G.,Argade, Narshinha P.
, p. 2068 - 2076 (2007/10/03)
The complex bioactive natural and unnatural benzopyran congeners have been synthesized using one-/two-step approaches in very good yields from the reactions of two different dihydroxyphthalides, natural resorcyclic acid derivative, and trihydroxybenzophenone with citral and/or farnesal, via the phenol-driven intramolecular diastereoselective thermal/base-catalyzed dipolar [2 + 2] cycloaddition reactions and three different thermal intramolecular cyclization reactions. The effects of the nature and the position of phenolic groups in the starting materials on the course of these cycloaddition reactions have also been described. Depending upon the absence or presence of intramolecular hydrogen bonding of the phenolic group with the carbonyl moiety in the starting materials, these phenol-driven intramolecular thermal/base-catalyzed dipolar [2 + 2] cycloaddition reactions either furnished the kinetically controlled products or directly formed the thermodynamically controlled rearranged products, respectively.
Highly selective catalytic Friedel-Crafts acylation and sulfonylation of activated aromatic compounds using indium metal
Jang, Doo Ok,Moon, Kyung Soo,Cho, Dae Hyan,Kim, Joong-Gon
, p. 6063 - 6066 (2007/10/03)
The Friedel-Crafts acylation of activated benzenes with various aromatic and aliphatic acid chlorides was studied in the presence of indium metal. The reaction was accomplished in high isolated yields under solvent or solvent-less conditions. The method is also applicable for preparing diaryl sulfones from aromatic compounds and aryl sulfonyl chlorides.
