101693-93-0

Usage

Uses

Used in Pharmaceutical Industry:
(5R)-5-Methyl-2-(phenylthio)-cyclohexanone (Mixture of Diastereomers) is used as an intermediate in the preparation of Artemisinin and Ptilocaulin. Artemisinin is a potent antimalarial drug, while Ptilocaulin has potential applications in the treatment of various diseases. The compound's unique structure and properties make it a valuable building block in the synthesis of these pharmaceuticals.
Used in Chemical Synthesis:
(5R)-5-Methyl-2-(phenylthio)-cyclohexanone (Mixture of Diastereomers) can be utilized as a key intermediate in the synthesis of various organic compounds. Its chemical properties, such as the presence of the cyclohexanone ring and the phenylthio group, allow for further functionalization and modification to create a wide range of products with different applications.
Used in Research and Development:
Due to its unique structure and potential applications, (5R)-5-Methyl-2-(phenylthio)-cyclohexanone (Mixture of Diastereomers) is also used in research and development for the exploration of new chemical reactions, synthesis methods, and potential applications in various fields. Researchers can use (5R)-5-Methyl-2-(phenylthio)-cyclohexanone (Mixture of Diastereomers) to study its reactivity, stability, and other properties, which can lead to the discovery of new compounds and applications.

Upstream product

• 308358-04-5 (6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one 
• 108-98-5 thiophenol 
• 13368-65-5 (3R)-3-methylcyclohexanone 
• 882-33-7 diphenyldisulfane 
• 930-69-8 sodium thiophenolate 
• 89-82-7 pulegone 
• 90461-82-8 Sodium; (R)-5-methyl-2-phenylsulfanyl-cyclohex-1-enolate 

Downstream Products

• 88154-77-2 (5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one 
• 54307-74-3 (R)-5-methyl-cyclohex-2-enone 
• 216865-95-1 (1R,3R)-5-Methyl-2-phenylsulfanyl-cyclohexane-1,3-diol 
• 1225377-92-3 3-((4R)-4-methyl-2-oxo-1-(phenylthio)cyclohexyl)propyl acetate 
• 1438285-30-3 (R)-2-(3-chloropropyl)-5-methylcyclohex-2-enone 
• 1438285-90-5 2-((1S,2R,3S,5R)-3-ethynyl-3-hydroxy-2-(3-hydroxypropyl)-5-methylcyclohexyl)acetonitrile 
• 1225377-69-4 2-((1S,2R,3R,5R)-3-ethynyl-2-(3-hydroxypropyl)-3-(benzylamino)-5-methylcyclohexyl)acetonitrile 
• 1225377-96-7 2-((1S,2R,3R,5R)-3-ethynyl-2-(3-hydroxypropyl)-3-((4-methoxybenzyl)amino)-5-methylcyclohexyl)acetonitrile 
• 1438285-83-6 C₄₄H₅₈N₄O₂Si 
• 1438285-84-7 C₄₄H₅₈N₄O₂Si 
• 1225377-71-8 2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile 
• 1438285-85-8 C₄₄H₅₈N₄OSi 
• 1438285-86-9 C₄₄H₅₈N₄OSi 
• 1225377-97-8 2-((4aR,5R,7S,8aS)-8a-ethynyl-1-(4-methoxybenzyl)-7-methyldecahydroquinolin-5-yl)acetonitrile 

Relevant academic research and scientific papers

Enantiospecific synthesis of rpr 107880 : A new non peptide substance P antagonist

The synthesis of enantiomerically pure RPR 107880 is described. The synthetic strategy is based on the use of the readily available and inexpensive (R)-(+)-pulegone. Copyright

The first asymmetric total synthesis of lycoposerramine-R

The first asymmetric total synthesis of lycoposerramine-R, a Lycopodium alkaloid possessing a novel skeleton, was accomplished by a strategy featuring the stereoselective intramolecular aldol cyclization giving a cis-fused 5/6 bicyclic skeleton and a new method for the construction of the pyridone ring via the aza-Wittig reaction.

Efforts toward the synthesis of (+)-Lyconadin A

Abstract: Synthetic efforts toward the synthesis of (+)-lyconadin A are described. B-Alkyl Suzuki coupling is utilized for combining 2-iodo cyclohexenone with the piperidine subunit. The piperidine subunit is derived from 5-bromo-3-nicotinic acid, and iod

Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids

Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.

A concise asymmetric total synthesis of (+)-fawcettimine

A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/

Complanadine A, a selective agonist for the Mas-related G protein-coupled receptor X2

The first biological target for the natural product complanadine A has been determined. The pseudosymmetric alkaloid functions as a selective agonist for the Mas-related G protein-coupled receptor X2 (MrgprX2), a G protein-coupled receptor that is highly expressed in neurons. Given the potential of MrgprX2 to function as a modulator of pain, complanadine A represents a new chemical probe to selectively interrogate the physiological function of MrgprX2 as well as a potential lead for the development of antihyperalgesics for the treatment of persistent pain. While complanadine A possess agonistic activity the related natural product lycodine, representing half of complanadine A, lacks activity providing a cursory description of the structural requirements for agonistic activity.

Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions

The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycodine core.

Total synthesis of (+)-fawcettidine

(Chemical Equation Presented) Alkaloids alchemy: A synthesis of the Lycopodium alkaloid (+)-fawcettidine (see structure) has been developed which requires 16 steps from (R)-(+)-pulegone as the chiral starting material. Key steps include a platinum(II)-cat

Stereoselective synthesis of (+)-2-deoxyolivin based on cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivative

The olivomycins are representative antitumor antibiotics in the aureolic family of the compounds, which contains the tricyclic aglycon core, olivin. In this study, we established the efficient synthesis of the anthracenone core skeleton based on a cycload

New DNA binding ligands as a model of chromomycin A3

Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this study, new DNA-binding ligands were designed to mimic Chromomycin A3 (CRA3), which contains a hydroxylated tetrahydroanthracene