126812-30-4

Usage

Structure

Contains a cyclohexane ring attached to a carbonyl group

Type of compound

Derivative of isoindoline-1,3-dione

Usage

Commonly used in organic synthesis and pharmaceutical research

Applications

Preparation of various pharmaceuticals, agrochemicals, and other fine chemicals

Versatility

Has versatile reactivity and potential biological activities

Utility

Useful in the development of new drugs and chemicals for various applications.

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 98-89-5 Cyclohexanecarboxylic acid 

Downstream Products

• 17496-14-9 2,3-dihydro-2-methyl-1H-inden-1-one 
• 36947-70-3 2-cyclohexylbenzimidazole 
• 1401413-07-7 N-(bis(4-methoxyphenyl)methylene)cyclohexanamine 
• 1358762-24-9 N-[bis(4-tolyl)methylene]cyclohexanamine 
• 18869-27-7 (E)-(2-cyclohexylvinyl)benzene 
• 40132-69-2 (Z )-1-(2-cyclohexyl-1-ethenyl)benzene 
• 4442-82-4 rac-2-cyclohexyl-1-phenylethan-1-ol 

Relevant academic research and scientific papers

Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters

An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.

Visible-Light-Triggered Decarboxylative Alkylation of 8-Acylaminoquinoline with N -Hydroxyphthalimide Ester

A facile protocol for visible-light-induced decarboxylative radical coupling of NHP esters with 8-aminoquinoline amides is reported, affording a highly efficient approach to synthesize a variety of 2-alkylated or 2,4-dialkylated 8-aminoquinoline derivativ

Visible Light-Induced Regioselective Decarboxylative Alkylation of the C(sp2)?H Bonds of Non-Aromatic Heterocycles

With sunlight or blue LEDs irradiation, regioselective decarboxylative alkylation of various non-aromatic heterocycles has been realized via C(sp3)-centered radical C(sp2)?C(sp3) bond formation under oxidant-free condition

Photoredox Decarboxylative C(sp3)-N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones

Herein we report a metal-free photocatalytic coupling reaction for the synthesis of structurally and functionally diverse N-alkyl hydrazones from α-diazoacetates and N-alkyl hydroxyphthalimide esters. By employing Rose Bengal as a photocatalyst with yellow LEDs irradiation, over 60 N-alkyl hydrazones were synthesized. Fluorescence quenching analysis and deuterium incorporation experiments reveal that Hantzsch ester serves as both an electron donor and proton source for the reaction. This strategy offers a simple retrosynthetic disconnection for conventionally inaccessible C(sp3)-rich N-alkyl hydrazones.

Catalyst-free Decarboxylation and Decarboxylative Giese Additions of Alkyl Carboxylates through Photoactivation of Electron Donor-Acceptor Complex

We report herein a catalyst-free method to perform decarboxylative conjugated addition and hydrodecarboxylation of aliphatic N-(acyloxy)phthalimides (redox active esters, RAEs) through photoactivation of electron-donor-acceptor (EDA) complex with Hantzsch ester (HE) in N,N-dimethylacetamide (DMA) solution. The reactions present a green method to decarboxylatively construct carbon-carbon bond and to perform hydrodecarboxylation with broad substrate scope and functional group tolerance under mild blue light irradiation condition without recourse of popularly used photoredox catalysts. (Figure presented.).

Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light

A synthetic method that enables the Hantzsch ester-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron-donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N-heterocycle.

Electroreductive Cross-Coupling of Trifluoromethyl Alkenes and Redox Active Esters for the Synthesis of Gem-Difluoroalkenes

An electroreductive access to gem-difluoroalkenes has been developed through the decarboxylative/defluorinative coupling of N-hydroxyphtalimides esters and α-trifluoromethyl alkenes. The electrolysis is performed under very simple reaction conditions in a

tert-Butyl Nitrite as a Twofold Hydrogen Abstractor for Dehydrogenative Coupling of Aldehydes with N-Hydroxyimides

A synthetically practical transition metal/catalyst/halogen-free dehydrogenative coupling of aldehydes with N-hydroxyimides promoted solely by tert-butyl nitrite under mild conditions was developed. tert-Butyl nitrite generates two radicals (tBuO and NO) and thus works as a twofold hydrogen abstractor. A diverse array of N-hydroxyimide esters were prepared from either aliphatic or aromatic aldehydes. Benzoyl-substituted aldehydes such as 2-oxo-2-phenylacetaldehyde are also suitable.

Substrate for synthesizing beta-Se amino acid as well as preparation method and application of substrate

The invention discloses a substrate for synthesizing beta-Se amino acid as well as a preparation method and application of the substrate, and the beta-Se amino acid is almost seldom synthesized by a method except selenocysteine at present. A substrate (namely a formula (I)) for synthesizing beta-Se amino acid is autonomously designed, and different beta-Se amino acids can be obtained only by changing a free radical precursor generated by photoreaction by using a general intermediate (namely the formula (I)) which is newly designed in the invention, so that divergent synthesis of the beta-Se amino acids is realized. According to the method for synthesizing the beta-Se amino acid, synthesis can be simply and efficiently achieved, good functional group compatibility can be achieved, the yield is generally high, and the application range of natural chemical connection is further expanded.

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.