18066-52-9

Upstream product

• 86728-36-1 Cyclohexyl 2-(Formyloxy)phenyl Ketone 
• 108-95-2 phenol 
• 3954-12-9 phenyl cyclohexanecarboxylate 
• 712-50-5 Cyclohexyl phenyl ketone 
• 108-85-0 1-bromocyclohexane 
• 611-20-1 salicylonitrile 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 110-82-7 cyclohexane 
• 90-02-8 salicylaldehyde 
• 931-50-0 cyclohexylmagnesium bromide 
• 119-36-8 methyl salicylate 
• 118-55-8 phenyl Salicylate 
• 86728-28-1 Methyl 2-Phenoxy-3-cyclohexyl-2-propenoate 

Downstream Products

• 5899-19-4 o-(α-cyclohexylmethyl)phenol 

Relevant academic research and scientific papers

Photochemistry of o-Allylphenol. Identification of the Minor Products and New Mechanistic Proposals

The photochemistry of o-allylphenol (1) in cyclohexane has been reinvetigated.Besides the previously reported cyclic ethers 2 and 3, seven additional minor photoproducts have been detected.Spectroscopic methods, coupled with independent synthesis, have allowed their identification as 2-methylbenzofuran (5), o-propylphenol (8), the epoxide 4, the dihydroxy compound 9, the cyclohexyl ether 6, o-(cyclohexylmethyl)phenol (10), and the dimer 7.Their formation is rationalized through new mechanistic pathways, which involve initial intermolecular electron and/or proton transfer between two molecules of o-allylphenol, as well as di-?-methane rearrangement.Key intermediates appear to be radical V, carbenium ion IX, and carbene XI.This is supported by photolysis of o-allylphenyl acetate (11), which leads to the formation of a radical pair, followed by in cage recombination to the photo-Fries products 12 and 13 or, alternatively, diffusion of the radicals out of the solvent cage to afford the minor products 2, 5, and 6, identical to those obtained by photolysis of 1.

Structure-activity relationships of novel salicylaldehyde isonicotinoyl hydrazone (SIH) analogs: Iron chelation, anti-oxidant and cytotoxic properties

Salicylaldehyde isonicotinoyl hydrazone (SIH) is a lipophilic, tridentate iron chelator with marked anti-oxidant and modest cytotoxic activity against neoplastic cells. However, it has poor stability in an aqueous environment due to the rapid hydrolysis of its hydrazone bond. In this study, we synthesized a series of new SIH analogs (based on previously described aromatic ketones with improved hydrolytic stability). Their structure-activity relationships were assessed with respect to their stability in plasma, iron chelation efficacy, redox effects and cytotoxic activity against MCF-7 breast adenocarcinoma cells. Furthermore, studies assessed the cytotoxicity of these chelators and their ability to afford protection against hydrogen peroxide-induced oxidative injury in H9c2 cardiomyoblasts. The ligands with a reduced hydrazone bond, or the presence of bulky alkyl substituents near the hydrazone bond, showed severely limited biological activity. The introduction of a bromine substituent increased ligand-induced cytotoxicity to both cancer cells and H9c2 cardiomyoblasts. A similar effect was observed when the phenolic ring was exchanged with pyridine (i.e., changing the ligating site from O, N, O to N, N, O), which led to pro-oxidative effects. In contrast, compounds with long, flexible alkyl chains adjacent to the hydrazone bond exhibited specific cytotoxic effects against MCF-7 breast adenocarcinoma cells and low toxicity against H9c2 cardiomyoblasts. Hence, this study highlights important structure-activity relationships and provides insight into the further development of aroylhydrazone iron chelators with more potent and selective anti-neoplastic effects.

Nickel-Catalyzed Directed Cross-Electrophile Coupling of Phenolic Esters with Alkyl Bromides

Herein, we demonstrate the successful use of robust phenolic esters as an electrophilic acyl source in the reaction with diverse primary and secondary unactivated alkyl bromides. The cleavage of the relatively inert C-O bond is facilitated by the neighboring coordinating hydroxyl or sulfonamide moiety. By circumventing the use of pregenerated organometallics, this method allows efficient preparation of a variety of o-hydroxyl and tosyl-protected o-amino aryl ketones with high compatibility with a wide range of functionalities.

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

A ketone the synthetic method of the compound of (by machine translation)

The invention discloses a method for the synthesis of ketone compound, the aldehyde compound and cyclanes mixed or dissolved in organic solvent, in the microwave radiation and presence of radical initiator under the condition of the 140 [...] 180 °C reaction to obtain the target product ketone compound, in the synthesis method of the reaction equation: , Wherein R 1 is phenyl or substituted phenyl, substituted phenyl benzene ring substituted the base is the fluorine, chloro, bromo, methyl, methoxy, trifluoromethyl or hydroxy in one or more of, the position of the substituent on the benzene ring is ortho, meta or para position, as n the 1 [...] 4 integer between the, free-radical initiator is benzoyl peroxide, di-tert-butyl peroxide, or cumyl peroxide, organic solvent as the alkane or benzene. The invention discloses method for the synthesis of the raw material is cheap and easy to obtain, good atom economy, wide range of the application of substrates, and the like, is suitable for industrial production. (by machine translation)

Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp3)-H Bond

In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp3)-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.

The insertion of arynes into the O-H bond of aliphatic carboxylic acids

The insertion of arynes into the O-H bond of aliphatic carboxylic acids promoted by sodium carboxylates is described. The reactions led to the formation of aryl carboxylates in good yields with good chemoselectivities under mild conditions.

Palladium-catalyzed ortho-CH-bond oxygenation of aromatic ketones

A palladium-catalyzed C(sp2)-H bond oxygenation reaction is described. This protocol represents the first example of a C-H bond cleavage/C-O bond formation sequence, by employing a ketone moiety as the directing group. With this new catalytic method, a variety of ortho-acylphenols can be easily accessed from arylketones.

An improved synthesis of hydroxy aryl ketones by fries rearrangement with methanesulfonic acid/methanesulfonic anhydride

Methanesulfonic acid treated with methanesulfonic anhydride effectively mediates the Fries rearrangement of aryl esters to give hydroxy aryl ketones with high yields. Georg Thieme Verlag Stuttgart · New York.

Synthetic Applications of Heteroatom-Directed Photoarylation. Benzofuran Ring Construction

The preparation of several α-phenoxy-α,β-unsaturated carboxylic acid esters via condensation of phosphonate 3c with ketones and an aldehyde is described.The resulting aryl vinyl ethers undergo photocyclization to give 2,3-dihydrobenzofuran-2-carboxylic