Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated synthesesElectronic supplementary information (ESI) available: experimental procedures for the preparation of 1,4-dihydrobiphenyl,9 1-deuterio-1,4-dihydrobiphenyl, 1-phenylcyclohexa-2,5-diene-1-carboxylic acid with 3,4-dihydrobiphenyl-3-carboxylic acid, 2-(cyclohex-2-enyloxy)ethyl 1-phenylcyclohexa-2,5-diene-1-carboxylate and non-1-en-6-ol. Experimental details of the reactions of cyclopentyl 1-phenylcyclohexa-

Baguley, Paul A.; Jackson, Leon V.; Walton, John C.

doi:10.1039/b110527m

Cited by 20 publications

(3 citation statements)

References 7 publications

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“…The synthesis of 3 (see Scheme 1) started with a Birch reduction of biphenyl 4 to generate diene 5. [10] Treatment of 5 with meta-chloroperbenzoic acid (mCPBA) generated the cis-diepoxide, 6, as the major diastereoisomer in a cis/trans ratio of 10:1. The minor diastereoisomer was readily removed by chromatography.…”

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confidence: 99%

Synthesis and Elaboration of All‐cis‐1,2,4,5‐Tetrafluoro‐3‐Phenylcyclohexane: A Polar Cyclohexane Motif

Durie

Fujiwara

Cormanich

et al. 2014

Chemistry A European J

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A stereocontrolled synthesis of all-cis-1,2,4,5- tetrafluoro-3-phenylcyclohexane is developed as the first functionalised example of this polar cyclohexane motif. The dipolar nature of the ring, arising due to two 1,3-diaxial C-F bonds, is revealed in the solid-state (X-ray) structure. The orthogonal conformation of the aryl and cyclohexyl rings in all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane, and in an ortho-nitro derivative, result in intramolecular (1h)JHF and (2h)JCF NMR couplings relayed through hydrogen bonding. The aryl group of all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane is elaborated in different ways to demonstrate the versatility of this compound for delivering the motif to a range of molecular building blocks.

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confidence: 99%

Synthesis and Elaboration of All‐cis‐1,2,4,5‐Tetrafluoro‐3‐Phenylcyclohexane: A Polar Cyclohexane Motif

Durie

Fujiwara

Cormanich

et al. 2014

Chemistry A European J

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“…According to our results, N-substituted 1,2-aminoalcohols 7-10 had a moderate activity against both Gram-negative and Gram-positive bacteria. Most of the ring-closing oxazolidine products (12)(13)(14) Molecules 2020, 25, 21 6 of 14 showed a similar moderate antibacterial activity. The removal of the nitrogen substituent of the aminoalcohols led to the loss of antibacterial activity (see amino diol 6).…”

Section: Antimicrobial Effectsmentioning

confidence: 96%

“…Due to the availability of these building blocks, numerous methods have been developed for the preparation of benzofuran systems [6][7][8][9][10][11]. However, only a few examples of the synthesis of octahydrobenzofuran derivatives have been reported including free-radical reactions [12,13], hydrogenation [14,15], tandem conjugate addition [16], base- [17] or acid-catalyzed cyclization [18], and photochemical rearrangement [19]. Furthermore, octabenzohydrofuran derivatives are well-known versatile precursors for the construction of a variety of therapeutic drugs [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core

et al. 2019

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A library of 1,2-aminoalcohol derivatives with a neoisopulegol-based octahydrobenzofuran core was developed and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The allylic chlorination of (+)-neoisopulegol, derived from natural (-)-isopulegol followed by cyclization, gave the key methyleneoctahydrobenzofuran intermediate. The stereoselective epoxidation of the key intermediate and subsequent oxirane ring opening with primary amines afforded the required 1,2-aminoalcohols. The ring closure of the secondary amine analogues with formaldehyde provided spiro-oxazolidine ring systems. The dihydroxylation of the methylenetetrahydrofuran moiety with OsO 4 /NMO (4-methylmorpholine N-oxide) resulted in the formation of a neoisopulegol-based diol in a highly stereoselective reaction. The antimicrobial activity of both the aminoalcohol derivatives and the diol was also explored. Molecules 2020, 25, 21 2 of 14 antimalarial [26-28], and antileishmanial [29] agents. The 1,2-aminoalcohol function is found in a broad range of β-adrenergic blockers that are used extensively in the management of cardiovascular disorders [30], including hypertension, angina pectoris and cardiac arrhythmias, and other disorders that are related to the sympathetic nervous system [31,32]. 1,2-aminoalcohols have also been demonstrated to be excellent chiral auxiliaries and chiral catalysts in asymmetric synthesis [33]. To achieve new, efficient, and commercially available chiral catalysts, natural chiral terpenes, such as α-pinene [34-38], β-pinene [34,39], (-)-3-carene [39,40], (-)-verbenone [41,42], (-)-fenchone [43,44], (+)-camphor [43,45,46], and (-)-menthone [47] have proven to be excellent sources for the synthesis of bifunctional chiral compounds and heterocycles.In the present work, we set out to create a compound library with a (+)-neoisopulegol-based octahydrobenzofuran core and 1,2-aminoalcohol moieties. The synthesis started from commercially available (-)-isopulegol and then utilizing the resulting 1,2-aminoalcohol derivatives as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde. Furthermore, the antimicrobial activities of the synthesized compounds were also tested on multiple bacterial and fungal strains. Results Synthesis of Key Intermediate 3Key intermediate (-)-3-methylenetetrahydrofuran 3 was prepared from commercially available (-)-isopulegol 1 by oxidizing its hydroxyl function, followed by the stereoselective reduction of the resulting carbonyl group, thus providing (+)-neoisopulegol 2 [48][49][50][51]. The allylic chlorination of (+)-neoisopulegol 2 was followed by the cyclization-produced (-)-methylenetetrahydrofuran 3 [52-55], which was transformed into (−)-methylenetetrahydrofuran 4 by allylic oxidation after applying the literature method [55,56] (Figure 1).

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1,4-Cyclohexadiene

Walton

Portela‐Cubillo

2007

Encyclopedia of Reagents for Organic Synthesis

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Cited by 20 publications

References 7 publications

Synthesis and Elaboration of All‐cis‐1,2,4,5‐Tetrafluoro‐3‐Phenylcyclohexane: A Polar Cyclohexane Motif

Synthesis and Elaboration of All‐cis‐1,2,4,5‐Tetrafluoro‐3‐Phenylcyclohexane: A Polar Cyclohexane Motif

Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core

1,4-Cyclohexadiene

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