564-94-3Relevant academic research and scientific papers
Aspect Cinetique des Substitutions Homolytiques Intramoleculaires. Decomposition de Peroxydes Insatures Derives du Pinane
Montaudon, Evelyne,Bourgeois, Marie-Josephe
, p. 9335 - 9342 (1994)
The decomposition, in dichloromethane, of β- and γ-unsaturated peroxides derived from pinane leads to transient tertiary pinanyl adduct radicals.The evolution of the reaction depends on the position of the insaturation.An intramolecular homolytic substitution gives functional pinanic epoxides in the first case; a β-scission followed by a hydrogen transfer yields functional p-menthenic peroxides in the second case.
Synthesis method of myrtenyl dihydrazide compound with fungal inhibition activity
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Paragraph 0046; 0049-0050, (2021/07/17)
A synthesis method of a myrtenyl dihydrazide compound with fungal inhibition activity comprises the following steps of: firstly, selectively oxidizing alpha-pinene into myrtenyl, further oxidizing the myrtenyl into myrtenic acid, then reacting the myrtenic acid with thionyl chloride to obtain myrtenic acid acyl chloride, and finally, carrying out hydrazinolysis reaction with a series of substituted benzoyl hydrazine or 2-pyridine formyl hydrazine under an anhydrous condition, and synthesizing to obtain the myrtenyl dihydrazide compound. A bacteriostatic activity test shows that the myrtenyl dihydrazide compound has excellent broad-spectrum inhibitory activity on various plant pathogenic fungi, and can be used as a lead compound of a novel agricultural bactericide.
Synthesis of Myrtenal-Based Nanocellulose/Diacylhydrazine Complexes with Antifungal Activity for Plant Protection
Cen, Bo,Duan, Wengui,Li, Baoyu,Lin, Guishan,Wang, Xiaoyu
, p. 12956 - 12965 (2021/11/17)
In search of novel bioactive compounds with excellent and broad-spectrum antifungal activity and nanopesticides with sustained releasing property, a series of novel myrtenal-based diacylhydrazines were designed, synthesized, and characterized. The preliminary bioassay showed that myrtenal-based 2-picolinyl hydrazide exhibited better or comparable antifungal activity than that of the commercial fungicides boscalid and chlorothalonil against the tested fungi. Furthermore, myrtenal-based nanocellulose was designed as a nanopesticide carrier and prepared from two biomass materials, bleached bagasse pulp and turpentine oil. Drug-loading capacities (LCs) of these carriers and sustained releasing properties of corresponding complexes were also evaluated, and the results indicated that the esterification reaction in the different solvents would affect the micromorphology of carriers, which was the important influential factor for loading or releasing drugs. To our delight, complex VIII-3 (LC = 0.32, total releasing amount/time = 99.8%/168 h) showed a macroporous framework with the drug evenly distributed across the opening network and staged drug-releasing performance that deserved further study as a nanopesticide.
Monoterpene-containing substituted coumarins as inhibitors of respiratory syncytial virus (Rsv) replication
Borisevich, Sophia S.,Galochkina, Anastasia V.,Khomenko, Tatyana M.,Korchagina, Dina V.,Nikolaeva, Yulia V.,Petukhova, Galina D.,Salakhutdinov, Nariman F.,Shtro, Anna A.,Volcho, Konstantin P.
, (2021/12/24)
Respiratory syncytial virus (RSV) is a critical cause of infant mortality. However, there are no vaccines and adequate drugs for its treatment. We showed, for the first time, that O-linked coumarin–monoterpene conjugates are effective RSV inhibitors. The most potent compounds are active against both RSV serotypes, A and B. According to the results of the time-of-addition experiment, the conjugates act at the early stages of virus cycle. Based on molecular modelling data, RSV F protein may be considered as a possible target.
Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology
Ganji, Suresh,Svensson, Fredric G.,Unelius, C. Rikard
, p. 3332 - 3337 (2020/11/30)
Herein we report the asymmetric syntheses of a number of oxygenated terpenoids that are of importance in the chemical ecology of bark beetles. These are pinocamphones, isopinocamphones, pinocarvones, and 4-thujanols (= sabinene hydrates). The camphones were synthesized from isopinocampheol, the pinocarvones from β-pinene, and the thujanols from sabinene. The NMR spectroscopic data, specific rotations, and elution orders of their stereoisomers on a chiral GC-phase (β-cyclodextrin) are also reported. This enables facile synthesis of pure compounds for biological activity studies and identification of stereoisomers in mixed natural samples.
Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst
Aberkouks, Abderrazak,Mekkaoui, Ayoub Abdelkader,Ait Ali, Mustapha,El Firdoussi, Larbi,El Houssame, Soufiane
, (2020/02/15)
Co-Ag supported on the SiO2 catalyst was synthesized by the sol-gel method and characterized using XRD, FT-IR, TG-DTG, BET, CV, and SEM/EDX analysis. The catalytic performance of the resulting catalyst was examined by the oxidation of mono and sesquiterpenic olefins using hydrogen peroxide and tert-butyl peroxide as oxidant agents. Various parameters such as catalyst amount, temperature, and solvents have been studied. The Co-Ag supported on the SiO2 catalyst showed a high activity, selectivity, and recyclability for the selected oxidation reaction.
A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant
Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li
supporting information, p. 2262 - 2267 (2019/04/17)
A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).
Oxidation of secondary alcohols using solid-supported hypervalent iodine catalysts
Ballaschk, Frederic,Kirsch, Stefan F.
supporting information, p. 5896 - 5903 (2019/11/11)
It is shown how secondary alcohols are oxidized to provide the corresponding ketones by use of Oxone and solid-supported hypervalent iodine catalysts. Under experimentally simple conditions with acetonitrile at elevated temperatures, excellent conversions were achieved with low catalyst loadings (0.2-5 mol%) when employing the conjugates 5 and 6 derived from IBX and IBS. The catalysts are broadly applicable to a range of alcohol substrates. Of primary importance with respect to sustainability issues, the metal-free catalysts are easily removed from the reaction mixture through filtration, and they can be re-used in oxidation processes for multiple times, without loss of catalytic activity.
One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina
Demidova, Yu. S.,Simakova,Estrada,Beloshapkin,Suslov,Volcho,Salakhutdinov,Simakov,Murzin, D. Yu.
, p. 3454 - 3464 (2019/11/03)
Abstract: One-pot bio-based myrtenol amination was studied in the presence of alumina supported Au, Au–Pd and Pd nanoparticles subjected to the thermal treatment under oxidizing or reducing atmosphere. Myrtenol amination with aniline was carried out under nitrogen atmosphere (9?bar) at 453?K using toluene as a solvent. The effect of the active metal along with the influence of redox pre-treatment on the catalytic behavior in the hydrogen borrowing reaction was explored. The catalyst characterization was done by transmission electron microscopy, X-ray photoelectron spectroscopy, inductively coupled plasma optical emission spectroscopy, nitrogen adsorption. The active metal and the catalysts redox pretreatment affected more noticeably selectivity to the reaction products rather than myrtenol conversion. Monometallic Au/Al2O3 catalyst promoted predominantly formation of the target secondary amine and the corresponding imine without a significant impact of the side reaction of C=C bond hydrogenation in myrtenol, whereas monometallic Pd catalyst activated C=C bond resulting in its hydrogenation. At the same time in the presence of Au–Pd simultaneous hydrogenation of both C=C and C=N bond occurred. Au–Pd catalysts activated in oxygen and hydrogen showed different catalytic activity determined by the composition of surface active sites. Monometallic gold catalyst was more effective in the hydrogen transfer in the case of substrates with competitive unsaturated functional groups. Graphic Abstract: [Figure not available: see fulltext.].
IBX as a catalyst for dehydration of hydroperoxides: Green entry to α,β-unsaturated ketones: Via oxygenative allylic transposition
Kuga, Tetsuya,Sasano, Yusuke,Iwabuchi, Yoshiharu
supporting information, p. 798 - 801 (2018/02/06)
A catalytic transformation of allylic hydroperoxides into α,β-unsaturated carbonyl compounds using IBX as a dehydration catalyst is described. The combination of a singlet oxygen ene reaction and the IBX-catalyzed dehydration provides α,β-unsaturated carbonyl compounds from alkenes via oxygenative allylic transposition with H2O as the only byproduct.
