Conformational Studies. VI.1 Intramolecular Hydrogen Bonding in Nonchair Conformations of cis,cis,cis-2,5-Dialkyl-1,4-cyclohexanediols2

Stolow, Robert D.; McDonagh, Paul M.; Bonaventura, Maria Marta

doi:10.1021/ja01065a012

Cited by 32 publications

(9 citation statements)

References 1 publication

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“…All chemicals and reagents were of analytical grade and were obtained from Sigma Chemical Co. (St Louis, MQ, USA), Aldrich Chemical Co. (Steineheim, Germany), Merck (Darmstadt, Germany) and Kemika (Zagreb, Croatia). Thymoquinone and thymohydroquinone was prepared in our laboratories using the methods of Kremers et al (1909) and Stolow et al (1964), respectively. The purity of thymoquinone and thymohydroquinone was authenticated by NMR (Bruker AMX-400) analyses.…”

Section: Methodsmentioning

confidence: 99%

In Vitro acetylcholinesterase inhibitory properties of thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone

Jukić

Politeo

Maksimović

et al. 2007

Phytotherapy Research

249

136

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The aim of this study was to examine in vitro the inhibitory activity exerted by the main constituents of essential oil obtained from the aromatic plant Thymus vulgaris L. on acetylcholinesterase (AChE). The total essential oil and selected compounds, specifically linalool and thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone, were tested for AChE inhibition. Thymohydroquinone exhibited the strongest AChE inhibitory effect over the range of concentrations. The AChE inhibitory potential decreased in the following order: thymohydroquinone > carvacrol > thymoquinone > essential oil > thymol > linalool. It is interesting that the AChE inhibitory effect exerted by carvacrol was 10 times stronger than that exerted by its isomer thymol, although thymol and carvacrol have a very similar structure.

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Section: Methodsmentioning

confidence: 99%

In Vitro acetylcholinesterase inhibitory properties of thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone

Jukić

Politeo

Maksimović

et al. 2007

Phytotherapy Research

249

136

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“…On the basis of this result, we envisaged that the axial-rich conformation of 5 was stabilized by hydrogen bondings. 16 Because the ring flip of 5 occurred in CD 3 CN (Table 1), we changed the solvent to CD 3 OD. The result listed in Table 2 indicated that the ring conformation of 5 was still the axial-rich chair form even in methanol.…”

Section: Considerations Of the Ring Conformationsmentioning

confidence: 99%

Achievement of ring inversion of myo-inositol derivatives due to silyloxy/silyloxy repulsion enhanced by the trans-substituents on both sides

et al. 2005

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“…In the literature, biscarbonyl 14 has already been reported in 1964 and 1971, but was not synthesized from renewable resources or in a sustainable fashion. The authors used a pathway starting from 2,5-dimethoxy-p-cymene applying lithium and ammonia in ethanol [44] or the oxidation of the corresponding diols via Jones oxidation applying highly toxic and carcinogenic chromium trioxide [45]. To the best of our knowledge, this is the first reported synthesis via a double rearrangement starting from bio-based γ-terpinene dioxide.…”

Section: (B) Substrate Broadeningmentioning

confidence: 99%

Sustainable catalytic rearrangement of terpene-derived epoxides: towards bio-based biscarbonyl monomers

Löser

Rauthe

Meier

et al. 2020

Phil. Trans. R. Soc. A.

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Seeking a sustainable and selective approach for terpene modification, a catalyst deconvolution approach was applied to the Meinwald rearrangement of (+)-limonene oxide as a model substrate to yield dihydrocarvone. In order to identify the most suitable catalyst and reaction conditions, different Lewis acids were evaluated. Bismuth triflate proved to be the most active catalyst under mild reaction conditions, with a low catalyst loading (1 mol%) and a relatively short reaction time (3 h). The optimized reaction conditions were subsequently transferred to other terpene-based epoxides, yielding different bio-based biscarbonyl structures, which constitute interesting and valuable substances, e.g. for polymer synthesis or as fragrances. Monoepoxides derived from ( R )-(−)-carvone and (+)-dihydrocarvone rearranged to the desired products with high selectivities and yields. γ-Terpinene dioxide could be transformed in a double rearrangement to the respective biscarbonyl in moderate yields. A better result was achieved for limonene dioxide after further adjustment of the protocol to reach acceptable yields with a low catalyst loading of 0.1 mol% using 2-methyl tetrahydrofuran as a sustainable solvent. Compared to many procedures described in the literature, this procedure represents a step towards an increased sustainability in terpene modification by considering several principles of Green Chemistry, such as renewable resources, catalysis and mild reaction conditions for elementary chemical transformations. This article is part of a discussion meeting issue ‘Science to enable the circular economy’.

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Conformational Studies. VI.¹ Intramolecular Hydrogen Bonding in Nonchair Conformations of cis,cis,cis-2,5-Dialkyl-1,4-cyclohexanediols²

Cited by 32 publications

References 1 publication

In Vitro acetylcholinesterase inhibitory properties of thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone

In Vitro acetylcholinesterase inhibitory properties of thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone

Achievement of ring inversion of myo-inositol derivatives due to silyloxy/silyloxy repulsion enhanced by the trans-substituents on both sides

Sustainable catalytic rearrangement of terpene-derived epoxides: towards bio-based biscarbonyl monomers

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