Graphite oxide-catalyzed acetylation of alcohols and phenols

Liu, Yuanyuan; Qi, Jun-Mei; Bai, Li-Sha; Xu, Yungen; Ma, Ning; Sun, Fangli

doi:10.1016/j.cclet.2016.01.005

Cited by 11 publications

(4 citation statements)

References 22 publications

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“…For compounds 4g–4j , R 2 was the straight chain with one, four, five or six carbon atoms, and R 1 was H atom. The target compounds were synthesized via a nucleophilic substitution reaction between intermediate 3a or 3e and the substituted acyl chloride (R 2 ‐COCl) in the presence of triethylamine according to a reported method 51 …”

Section: Resultsmentioning

confidence: 99%

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Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Yang

Pan

et al. 2022

Pest Management Science

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BACKGROUND Aphids have been mainly controlled by traditional chemical insecticides, resulting in unamiable risk to the environment over the last decades. Push–pull strategy is regarded as a promising eco‐friendly approach for aphid management through repelling aphid away and attracting their natural enemy. Methyl salicylate (MeSA), one of typical HIPVs (herbivore‐induced plant volatiles), can repel aphids and attract ladybugs. Our previous studies discovered a new lead compound 3e, a salicylate‐substituted carboxyl (E)‐β‐farnesene derivative that had effective aphid‐repellent activity. However, whether 3e has attractive activity to ladybug like MeSA is unknown. Meanwhile, to discover a new derivative for both deterring aphid and recruiting ladybug is meaningful for green control of aphids. RESULTS Through the structural optimization of 3e, 14 new derivatives were designed and synthesized. Among them, compounds 4e and 4i had good aphid (Acyrthosiphon pisum) repellent activity, and compounds 3e, 4e and 4i had significant ladybug (Harmonia axyridis) attractive activity to males. Particularly, 4i exhibited manifest attractive effect on the females as well. Binding mechanism showed that 4i not only bound effectively with the aphid (Acyrthosiphon pisum) target ApisOBP9 thanks to its multiple hydrophobic interactions and hydrogen‐bond, but also had strong binding affinity with ladybug target HaxyOBP15 due to the suitable steric space. Additionally, 4i displayed low toxicity to bee Apis mellifera. CONCLUSION Compound 3e does exhibit attractive activity to male ladybug as MeSA. However, the new derivative 4i, with both pleasant aphid‐repellent and ladybug‐attraction activities, can be considered as a novel potential push–pull candidate for aphid control in sustainable agriculture. © 2022 Society of Chemical Industry.

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Section: Resultsmentioning

confidence: 99%

“…The target compounds were synthesized via a nucleophilic substitution reaction between intermediate 3a or 3e and the substituted acyl chloride (R 2 -COCl) in the presence of triethylamine according to a reported method. 51 3.2 Binding affinity to ApisOBP9 and HaxyOBP15…”

Section: Design and Synthesis Of Target Compoundsmentioning

confidence: 99%

Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Yang

Pan

et al. 2022

Pest Management Science

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“…They can be used as active elements in electronic devices. − The photoluminescence properties of GO quantum dots are promising for use in sensors . Graphene oxides constitute a new class of metal-free catalysts for several important chemical reactions . Furthermore, “pristine” graphene flakes (themselves of nanotechnological interest) can be easily made by reducing individual layered structures exfoliated from oxidized graphite (reduced graphene oxides, rGOs) …”

Section: Introductionmentioning

confidence: 99%

Formation of Sublimable Nanographene Oxides by Reacting Coronene Films with Atomic Oxygen

et al. 2018

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We have studied the oxidation of multilayer thin films of coronene (C 24 H 12 ) on graphite under UHV conditions. Coronene films were grown by low-energy cluster ion beam deposition (LECBD, C 24 H 12 + , E kin < 6 eV) and subsequently oxidized by exposing them to a beam of nearthermal atomic oxygen at room temperature. Mass spectra recorded during sublimation of the oxidized coronene films reveal a distribution of emitted species, C 24 H 12 O n (n ≤ 7), which we assign as coronene epoxides. From the fragmentation pattern we infer that primarily rim epoxides are formed, which exhibit a higher stability than core epoxides according to DFT calculations. In addition to epoxides, XPS indicates that other oxidic functional groups, such as ethers, are also formed in smaller relative amounts as nonsublimable species. The overall yield for the thermal desorption of intact coronene oxides can be up to 7% of the deposited coronene, sufficiently high such that this procedure could be useful as a source of monodispersed nanoscale graphene oxides (nano-GOs) for applications in nanotechnology.

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“…Sulfonated activated carbon [14], [15], [16], and carbon-supported yttrium oxide [17] are examples of carbon-based catalysts that have been produced. Because of its high conversion in a short time under moderate reaction conditions, graphene oxide produced from graphite has also been described as an excellent catalyst for the acetylation of alcohols and phenols, in addition to being inexpensive, not excessively acidic and toxic, and environmentally benign [18]. Graphene oxide nanoribbons formed of multi-walled carbon nanotubes (MWCNT) have a very wide surface area, which speeds up the process of ion adsorption and diffusion onto the catalyst's surface [19].…”

Section: Article Historymentioning

confidence: 99%

Glycerol Acetylation: Effect of Graphene Oxide Catalyst Mass Percentage on Glycerol Conversion and Acetin Selectivity

Hidayati,

Prasetyo,

Brilianti

et al. 2023

CHEMICA: Jurnal Teknik Kimia

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Graphite oxide-catalyzed acetylation of alcohols and phenols

Cited by 11 publications

References 22 publications

Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Formation of Sublimable Nanographene Oxides by Reacting Coronene Films with Atomic Oxygen

Glycerol Acetylation: Effect of Graphene Oxide Catalyst Mass Percentage on Glycerol Conversion and Acetin Selectivity

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