34987-31-0

Usage

Uses

Used in Organic Synthesis:
2-CYCLOHEXYL-1,4-NAPHTHOQUINONE is used as a reactant in organic synthesis for the production of various chemical compounds and derivatives, leveraging its unique naphthoquinone structure.
Used in Dye Production:
In the dye industry, 2-CYCLOHEXYL-1,4-NAPHTHOQUINONE is utilized as a precursor to create a range of dyes, capitalizing on its chemical properties to impart color and stability.
Used in Antioxidant Formulation:
2-CYCLOHEXYL-1,4-NAPHTHOQUINONE is employed as an antioxidant, providing protection against oxidative stress in various applications, such as in the food and cosmetic industries, due to its ability to neutralize free radicals.
Used in Pharmaceutical Development:
In the pharmaceutical sector, 2-CYCLOHEXYL-1,4-NAPHTHOQUINONE is used as a precursor in the development of new drugs, particularly those with antimicrobial and anti-inflammatory properties, as it is being studied for its potential therapeutic effects.
Used in Medical Research:
2-CYCLOHEXYL-1,4-NAPHTHOQUINONE is used in medical research for exploring its potential as a therapeutic agent, focusing on its antimicrobial and anti-inflammatory properties, with ongoing studies to determine its efficacy and safety in treating various conditions.
It is crucial to handle 2-CYCLOHEXYL-1,4-NAPHTHOQUINONE with care due to its potential hazards if not properly managed, ensuring safe practices in storage and usage across different industries.

InChI:InChI=1/C16H16O2/c17-15-10-14(11-6-2-1-3-7-11)16(18)13-9-5-4-8-12(13)15/h4-5,8-11H,1-3,6-7H2

Upstream product

• 34987-30-9 2-(cyclohexyl)-1,4-di-(hydroxy)-naphthalene 
• 931-48-6 2-cyclohexylacetylene 
• 4900-63-4 1-methoxy-4-nitronaphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 110-83-8 cyclohexene 
• 110-82-7 cyclohexane 
• 4441-56-9 cyclohexylboronic acid 
• 1088-01-3 tricyclohexylborane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 106-99-0 buta-1,3-diene 
• 591-51-5 phenyllithium 
• 108-86-1 bromobenzene 
• 98-89-5 Cyclohexanecarboxylic acid 
• 35448-12-5 2-(cyclohexyloxy)-2-oxoacetic acid 

Downstream Products

• 41245-70-9 1a-cyclohexyl-1a,7a-dihydronaphth<2,3b>oxirene-2,7-dione 
• 73377-78-3 (+)-2-Cyclohexyl-1,4-naphthoquinone 2,3-epoxide 
• 105016-64-6 (2S,3R)-2-cyclohexyl-2,3-epoxy-1,4-naphthoquinone 
• 73377-78-3 (2R,3S)-2-cyclohexyl-2,3-epoxy-1,4-naphthoquinone 
• 41245-70-9 7a-Cyclohexyl-1a,7a-dihydro-1-oxa-cyclopropa[b]naphthalene-2,7-dione 
• 54812-04-3 2‐cyclohexyl‐3‐methylnaphthalene‐1,4‐dione 
• 4042-30-2 parvaquone 

Relevant academic research and scientific papers

Simple and effective route for synthesis of parvaquone, an antiprotozoal drug

Parvaquone, an antiprotozoal agent against Theileria parva, was synthesized in 33.8% overall yield by using cheap, commercially available raw materials. A key intermediate, 2-cyclohexyl-1-naphthol, was synthesized in 86% yield by cyclohexylation of 1-naphthol and further converted into parvaquone in good yield through reaction sequences such as oxidation and epoxidation followed by isomerization.

A free radical alkylation of quinones with olefins

We demonstrated herein an Fe(iii)-mediated radical alkylation of quinones. A wide range of bioactive molecules with quinone motifs can be rapidly synthesized by using readily available and inexpensive NaBH4/NaBD4 with alkenes at room temperature under open flask conditions.

Quinone C-H Alkylations via Oxidative Radical Processes

A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C-H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.

Metal-, Photocatalyst-, and Light-Free, Late-Stage C-H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids

Contrary to the accepted convention, this work shows that Minisci-type C-H alkylation does not require any metal, photocatalyst, light, or prefunctionalization of the readily available and inexpensive carboxylic acids to proceed well under mild conditions. These mild conditions can be utilized for late-stage alkylations of complex molecules, including pharmaceutical compounds and light-sensitive compounds which degrade under photocatalytic conditions.

Naphthoquinone Derivatives, Benzoquinone Derivatives, and Anthracenedione Derivatives, Their Use and Novel Method for Preparation

The present invention relates to: a novel manufacturing method of quinone derivatives or anthracenedione derivatives by a copper-catalyzed cross-dehydrogenation coupling reaction of naphthoquinone, benzoquinone or anthracenedione compounds with various cycloalkanes; naphthoquinone derivatives, benzoquinone derivatives and anthracenedione derivatives; and uses thereof. According to the novel manufacturing method of the present invention, since the naphthoquinone derivatives, benzoquinone derivatives or anthracenedione derivatives can be prepared in one step, manufacturing efficiency is improved and cost and time can be saved, and the derivatives according to the present invention can be variously used as an animal medicine.COPYRIGHT KIPO 2019

Ir-catalyzed arylation, alkylation of quinones with boronic acids through C-C coupling

Ir-catalyzed arylation, alkylation of quinones with boronic acids was developed under room temperature. Both aryl and alkyl boronic acids are suitable for this transformation. This expands the application scope of the iridium catalyst. This is also an excellent proof that iridium catalysts can be used in the C-C coupling of quinones and naphthoquinones with alkyl boronic acids.

Synthesis of aryl- and alkylquinones through rhodium-catalyzed C-C coupling under mild conditions

A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C-C coupling has been developed under mild conditions. [CpRhCl2]2 was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.

Total synthesis of parvaquone and the serendipitous discovery of a novel chromium-mediated method for β-lactone formation

During attempts to synthesise the 2-hydroxy-1,4-naphthoquinone, parvaquone, 1, a novel chromium-mediated method for the synthesis of functionalised β-lactones from propargyl alcohols has been discovered. Additionally, using both dry state and ultrasound conditions, the total synthesis of parvaquone (1) has been achieved; the most efficient techniques deliver this target compound in up to 46% overall yield over, as low as, two synthetic processes.

A New Selective Method for the Homolytic Alkylation and Carboxylation of Quinones by Monoesters of Oxalic Acid

Alkyl and alkoxycarbonyl radicals were generated by oxidative decarboxylation of oxalic acid monoesters by persulfate; they were then utilized for the selective substitution of quinones.

REDUCTION OF NITRONATE ADDUCTS FROM RMgX AND 1-METHOXY-4-NITRO-NAPHTHALENE TO OXIMES OR AMINES BY TRIVALENT PHOSPHORUS REAGENTS

The reduction of nitronate adducts from 1-methoxy-4-nitronaphthalene and Grignard reagents (CH3MgX, PhCH2CH2MgX, i-C3H7MgX, c-C6H11MgX and t-C4H9MgX) with hexamethyl phosphorous triamide and phosphorous trichloride is reported.With the former reagent the reaction is chemio and stereoselective and only the E-oxime is recovered being the E-2-alkyl-4-methoxy-1(2H)naphthalenone oximes and the E-2-alkyl-2,3-dihydro-1,4-naphthoquinone-1-oximes obtained after quenching with NH4Cl and HCl respectively.Oxime stereochemistry is assigned by LIS values caused by Eu(dpm)3 on (13)C signals of 2-methyl-4-methoxy-1-(2H)naphthalenone oxime and 2-methyl-2,3-dihydro-1,4-naphthoquinone-1-oxime.Complete reduction to amines is obtained with phosphorous trichloride.