2789-44-8

Usage

InChI:InChI=1/C14H18O/c1-11-7-9-13(10-8-11)14(15)12-5-3-2-4-6-12/h7-10,12H,2-6H2,1H3

Upstream product

• 931-51-1 cyclohexylmagnesiumchloride 
• 98-86-2 acetophenone 
• 108-88-3 toluene 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 98-89-5 Cyclohexanecarboxylic acid 
• 108-85-0 1-bromocyclohexane 
• 104-87-0 4-methyl-benzaldehyde 
• 624-31-7 4-tolyl iodide 
• 4354-49-8 2-cyclohexyl-2-oxoethanoic acid 
• 110-82-7 cyclohexane 
• 60718-41-4 Se-phenyl cyclohexanecarboselenoate 
• 66117-64-4 di(p-tolyl)borinic acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 93765-29-8 Cyclohexyl-pyrimidin-5-yl-p-tolyl-methanol 
• 128352-34-1 methyl E-2-(o-carboxyphenyl)-3-cyclohexyl-p-methylcinnamate 
• 128352-40-9 methyl Z-2-(o-carboxyphenyl)-3-cyclohexyl-p-methylcinnamate 
• 409326-90-5 4-cyclohexanoylbenzoic acid 
• 92298-94-7 1-(cyclohexylmethyl)-4-methylbenzene 
• 28047-28-1 cyclohexyl-(p-methylphenyl)-methanol 
• 868396-29-6 3-cyclohexyl-3-hydroxy-1-piperidin-1-yl-3-p-tolyl-propan-1-one 
• 1355254-07-7 C₁₈H₂₈OSi 
• 20112-74-7 cyclohexyl(2-hydroxy-4-methylphenyl)methanone 
• 1428245-10-6 cyclohexyl(2,6-dihydroxy-4-methylphenyl)methanone 
• 133047-88-8 1-hydroxycyclohexyl-(4-methylphenyl)methanone 
• 28047-24-7 (Chlor)cyclohexyl(p-tolyl)methan 
• 7577-04-0 4-(1-cyclohexenylmethyl)toluene 
• 7577-03-9 1-(cyclohexylidenemethyl)-4-methylbenzene 

Relevant academic research and scientific papers

Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkyl Amides

We report the Pd-catalyzed Suzuki-Miyaura cross-coupling of aliphatic amides. Although tremendous advances have been made in the cross-coupling of aromatic amides, C-C bond formation from aliphatic amides by selective N-C(O) cleavage has remained a major challenge. This longstanding problem in Pd catalysis has been addressed herein by a combination of (1) the discovery of N,N-pym/Boc amides as a class of readily accessible amide-based reagents for cross-coupling and (2) steric tuning of well-defined Pd(II)-NHC catalysts for cross-coupling. The methodology is effective for the cross-coupling of an array of 3°, 2°, and 1° aliphatic amide derivatives. The catalyst system is user-friendly, since the catalysts are readily available and are air- and bench-stable. Mechanistic studies strongly support an amide bond twist and external nN → π*C═O/Ar delocalization as a unified enabling feature of N,N-pym/Boc amides in selective N-C(O) bond activation. The method provides a rare example of Pd-NHC-catalyzed cross-coupling of aliphatic acyl amide electrophiles.

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.

MODULATORS OF HSD17B13 AND METHODS OF USE THEREOF

The disclosure relates to compounds and pharmaceutical compositions capable of modulating the hydroxysteroid 17-beta dehydrogenase (HSD17B) family member proteins including inhibiting the HSD17B member proteins, e.g. HSD17B13. The disclosure further relates to methods of treating liver diseases, disorders, or conditions with the compounds and pharmaceutical compositions disclosed herein, in which the HSD17B family member protein plays a role.

Self-Assembled 2,3-Dicyanopyrazino Phenanthrene Aggregates as a Visible-Light Photocatalyst

In this study, 2,3-dicyanopyrazino phenanthrene (DCPP), a commodity chemical that can be prepared at an industrial scale, was used as a photocatalyst in lieu of Ru or Ir complexes in C-X (X = C, N, and O) bond-forming reactions under visible-light irradiation. In these reactions, [DCPP]n aggregates were formed in situ through physical π-πstacking of DCPP monomers in organic solvents. These aggregates exhibited excellent photo- and electrochemical properties, including a visible light response (430 nm), long excited-state lifetime (19.3 μs), high excited-state reduction potential (Ered([DCPP]n*/[DCPP]n·-) = +2.10 V vs SCE), and good reduction stability. The applications of [DCPP]n aggregates as a versatile visible-light photocatalyst were demonstrated in decarboxylative C-C cross-coupling, amidation, and esterification reactions.

Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.

Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis

Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C-H bonds, facilitating visible light-catalyzed construction of a variety of ketones. Tetrabutylammonium decatungstate and anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested a Pd0-PdII-PdIII-PdI-Pd0 pathway and revealed that regeneration of the Pd0 catalyst and the photocatalyst occurs simultaneously in the presence of KHCO3. This regeneration features a low energy barrier, promoting efficient coupling of the palladium catalytic cycle with the photocatalytic cycle. The work reported herein suggests great promise for further applications of HAT photocatalysis in palladium-catalyzed cross-coupling and C-H functionalization reactions to be successful.

Method for synthesizing aryl ketone compound by taking TBADT as photocatalyst

The invention provides a method for synthesizing an aryl ketone compound by taking TBADT as a photocatalyst. The method comprises the following steps: with TBADT as a photocatalyst, under the conditions of a palladium catalyst, a phosphine ligand, weak base and an organic solvent, irradiating the reactants under a 380-400 nm photocatalysis lamp at the room temperature under the inert protective atmosphere, so that an aldehyde group-containing compound reacts with Ar-X, wherein the Ar-X is aryl halide or aryl trifluoromethanesulfonate, and the aryl halide is aryl bromide or aryl iodide; the aldehyde group-containing compound is one of aryl aldehyde, alkyl aldehyde, linear primary aldehyde, acyclic secondary aldehyde and N-methylformamide. According to the invention, the tetrabutylammonium sebacate (TBADT)HAT photocatalyst and palladium catalysis are combined for use, and aldehyde C-H arylation and alkenylation reactions can be directly carried out to synthesize ketone. The method has the advantages of mild reaction conditions, high yield and wide substrate application range, and can be used for synthesizing natural products in medicinal plants.

Cross-Coupling of Secondary Amides with Tertiary Amides: The Use of Tertiary Amides as Surrogates of Alkyl Carbanions for Ketone Synthesis

In recent years, exciting progress has been made in the field of direct transformation of amides, nevertheless, the condensation between two amides remains rare and restricted to homo-coupling reactions. Herein, we report the cross-coupling of secondary amides with tertiary amides, which provides a synthesis of ketones under mild conditions, and features the use of tertiary amides as surrogates of alkyl carbanions. The method relies on the coupling of enamines, generated from tertiary amides by catalytic partial reduction of tertiary amides with Vaska's catalyst, with nitrilium ions, formed in situ from secondary amides via activation with trifluoromethanesulfonic anhydride, and on the subsequent deformylation.

Photocatalytic synthesis method of 1-hydroxyl cyclohexyl phenyl ketone compound and application thereof

A photocatalytic synthesis method of a 1-hydroxyl cyclohexyl phenyl ketone compound comprises the following steps that (a) 4-Ryl benzaldehyde and cyclohexane produce free radical reaction under the irradiation of an ultraviolet lamp to obtain 4-Ryl cyclohexyl phenyl ketone; (b) the 4-Ryl cyclohexyl phenyl ketone uses dimethyl sulfoxide as a solvent, uses hydrobromic acid as a bromine source, hydroxyl substitution is performed to obtain 1-hydroxyl cyclohexyl-(4-R phenyl) ketone, and the dimethyl sulfoxide is removed for recycle through distillation. A 1-hydroxyl cyclohexyl-(4-R phenyl) ketone coarse product is obtained through a crystallization method, and a 1-hydroxyl cyclohexyl-(4-R phenyl) ketone photoinitiator finished product is obtained through recrystallization. The synthesis methodhas the advantages that the synthesis steps of the method are simple, the preparation cost is low and no pollution is produced. The prepared cyclohexyl phenyl ketone compound is suitable for the efficient photoinitiator of UV light curing system, the product has better non-yellowing characteristic under the irradiation of an ultraviolet source, and popularization and development of a UV light curing technology are facilitated.

Photocatalytic synthesis method and application of cyclohexyl-(4-Rphenyl)ketone compound

Disclosed is a photocatalytic synthesis method of a cyclohexyl-(4-Rphenyl)ketone compound. 4-Rbenzaldehyde and cyclohexane are subjected to a free radical reactor under ultraviolet light illuminationto obtain the cyclohexyl-(4-Rphenyl)ketone compound, wherein an initiator of the free radical reactor is azobisisobutyronitrile or benzoyl peroxide or acetone, cyclohexane serves as a reactant and a solvent, after the free radical reactor, cyclohexane is recovered through distillation under reduced pressure, and residues are crystallized to obtain the cyclohexyl-(4-Rphenyl)ketone compound. The method is applied to a photocatalytic reactor to obtain cyclohexyl phenyl ketone, cyclohexane is recycled, and the preparation method has the advantages that the reactor conditions are mild, the processflow is simple, no pollution is caused, the materials are cheap, the yield is high, application of carcinogenic chemicals such as benzene is avoided, the synthesis steps are simple, the preparation cost is low, and no pollution is caused.