Regioselectivity in the intramolecular carbon–hydrogen insertion in metal-catalysed decomposition of some cis-1-methyl-3-arylcyclohexyl diazomethyl ketones. A highly efficient homogeneous nickel catalyst for carbenoid insertion

Chakraborti, Asit K.; Ray, Jayanta K.; Kundu, Kalyan K.; Chakrabarty, Sephali; Mukherjee, Debabrata; Ghatak, Usha Ranjan

doi:10.1039/p19840000261

Cited by 14 publications

(2 citation statements)

References 8 publications

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“…The formation of 4 from (-)- 3a via metal ammonia mediated chemo- and regio-selective hydrogenolysis 17, 18 (Scheme 2) further corroborated the stereo-preference in the Prins reaction of benzaldehyde and (+)-isopulegol as (1 S ,3 S ,6 S ,7 S ,9 S )-octahydro chromenol. 19…”

Section: Resultsmentioning

confidence: 57%

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

Slater

Lasonkar

Haider

et al. 2018

Tetrahedron Letters

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Novel, functionalized octahydrochromene derivatives were synthesized in a single step the Prins reaction. Enantiomerically pure (+)-isopulegol was reacted with benzaldehyde to stereoselectively yield the corresponding octahydro-2-chromen-4-ol derivative containing five stereocenters. A total of 10 compounds were synthesized by altering the enantiomer of isopulegol and the substituted benzaldehyde, and the resulting enantiopure octahydrochromenes were screened against the cannabinoid receptor isoforms CB1 and CB2. Compounds containing an olefin at the C4 position [(+)-, (-)-, (-)-, (-)- and (-)-] of the octahydrochromene scaffold were found to exhibit reasonable displacement of [H] CP55,940 from the CB receptors, whereas the corresponding hydroxy analogs [(+)-, (+)-, (-)-, (-)- and (+)-] had very little or no effect.

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Section: Resultsmentioning

confidence: 57%

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

Slater

Lasonkar

Haider

et al. 2018

Tetrahedron Letters

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“…Therefore, we regarded structure A as a candidate of higher priority and first prepared its precursor, ester 4a -Bn (Scheme S1), with the relative configuration of the three stereocenters as in compound A . We used the same methodology as reported for 5,5-dimethylcyclohex-2-enone, ,, starting from 3,5-dimethylcyclohex-2-en-1-one ( 1 ) (see Section S-1). However, compound 19 (Scheme in Section ), the salicylic acid ester compound A , turned out not to be the desired metabolite HMS-CA 5 (see Section S-2.1 peak assignment) but instead HMS-CA 6, which could not be confirmed in urine after dermal HMS application.…”

Section: Resultsmentioning

confidence: 99%

Identification, Organic Synthesis, and Sensitive Analysis of a cis-Homosalate-Specific Exposure Biomarker

Ebert,

Belov,

John

et al. 2024

Chem. Res. Toxicol.

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Homosalate (HMS) is an organic UV filter used in sunscreens and personal care products. Despite its widespread use and detection in environmental matrices, little is known regarding its exposure in humans. HMS is used as a mixture of cis-and transisomers, and we recently revealed major differences in human toxicokinetics, indicating the need to consider these isomers separately in exposure and risk assessments. In the course of these previous investigations of human HMS toxicokinetics, we identified two trans-HMS-specific and one cis-HMS-specific biomarker candidates. However, the latter lacks sensitivity due to only low amounts excreted in urine, prompting the search for another cis-HMS-specific biomarker. Our toxicokinetic investigations revealed a total of five isomers of HMS carboxylic acid metabolites (HMS-CA). Of these, only one was specifically formed from cis-HMS (HMS-CA 5), but its full identity in terms of constitution and configuration had, so far, not been elucidated. Here, we describe the synthesis of three HMS-CA isomers, of which the isomer (1R,3S,5S)/ (1S,3R,5R)-3-((2-hydroxybenzoyl)oxy)-1,5-dimethylcyclohexane-1-carboxylic acid turned out to be HMS-CA 5. Taken together with two previously synthesized HMS-CA isomers, we were able to identify the constitution and configuration of all five HMS-CA isomers observed in human metabolism. We integrated the newly identified cis-HMS-specific metabolite HMS-CA 5 into our previously published human biomonitoring LC-MS/MS method. Intra-and interday precisions had coefficients of variation below 2% and 5%, respectively, and the mean relative recovery was 96%. The limit of quantification in urine was 0.02 μg L −1 , enabling the quantification of HMS-CA 5 in urine samples for at least 96 h after sunscreen application. The extended method thus enables the sensitive and separate monitoring of cis-and trans-HMS in future human biomonitoring studies for exposure and risk assessment.

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ChemInform Abstract: Regioselectivity in the Intramolecular Carbon‐Hydrogen Insertion in Metal‐catalysed Decomposition of Some cis‐1‐Methyl‐3‐arylcyclohexyl Diazomethyl Ketones. A Highly Efficient Homogeneous Nickel Catalyst for Carbenoid Insertion.

Chakraborti¹,

Ray²,

Kundu³

et al. 1984

Chemischer Informationsdienst

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Regioselectivity in the intramolecular carbon–hydrogen insertion in metal-catalysed decomposition of some cis-1-methyl-3-arylcyclohexyl diazomethyl ketones. A highly efficient homogeneous nickel catalyst for carbenoid insertion

Cited by 14 publications

References 8 publications

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

Identification, Organic Synthesis, and Sensitive Analysis of a cis-Homosalate-Specific Exposure Biomarker

ChemInform Abstract: Regioselectivity in the Intramolecular Carbon‐Hydrogen Insertion in Metal‐catalysed Decomposition of Some cis‐1‐Methyl‐3‐arylcyclohexyl Diazomethyl Ketones. A Highly Efficient Homogeneous Nickel Catalyst for Carbenoid Insertion.

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