共查询到20条相似文献,搜索用时 15 毫秒
1.
Roman O. Iakovenko Andrea Chicca Daniela Nieri Ines Reynoso-Moreno Jürg Gertsch Mikhail Krasavin Aleksander V. Vasilyev 《Tetrahedron》2019,75(5):624-632
A series of 1-trifluoromethyl substituted indanes and indenes bearing aryl groups in positions 1 and/or 3 of the indane core have been synthesized mainly by electrophilic cyclization and arylation of the corresponding trifluoromethylated allyl and propargyl alcohols. The distinctly lipophilic compounds thus obtained were tested against various components of human endocannabinoid system. None of the compounds displayed affinity toward CB1 or CB2 receptors. Two compounds inhibited monoacylglycerol lipase (MAGL) and three compounds showed inhibition of anandamide (AEA) uptake. The latter can be related to the low-micromolar inhibition of fatty acid amide hydrolase (FAAH) inhibition displayed by one of these compounds. 相似文献
2.
Palladium-catalyzed heck arylations of allyl alcohols in ionic liquids: remarkable base effect on the selectivity 总被引:1,自引:0,他引:1
Pd-catalyzed Heck arylation of allyl alcohols in tetraalkylammonium ionic liquids (ILs) can be made highly selective toward the formation of either aromatic carbonyl compounds or aromatic conjugated alcohols by carefully choosing both the IL and the base. 相似文献
3.
Takanari Matsutani Dr. Takashi Sakuramoto Kento Okabayashi Prof. Mamoru Tobisu Prof. Toshiyuki Moriuchi 《European journal of organic chemistry》2023,26(14):e202201410
Oxovanadium(V)-catalyzed deoxygenative coupling reaction of allyl alcohols with trimethylsilyl enol ethers was demonstrated to afford γ,δ-unsaturated carbonyl compounds in one-step. The catalytic deoxygenative coupling reaction of allyl alcohols proceeded smoothly with both aromatic and aliphatic trimethylsilyl enol ethers. This catalytic deoxygenative coupling system could be applied to the deoxygenative coupling reaction of benzyl alcohols with trimethylsilyl enol ethers, providing the corresponding carbonyl compounds. Furthermore, a gram-scale catalytic synthesis of the γ,δ-unsaturated carbonyl compound was successfully performed to validate the scalability of this catalytic deoxygenative coupling reaction. 相似文献
4.
A. A. Il’in A. N. Il’in Yu. L. Bakhmutov G. G. Furin L. M. Pokrovskii 《Russian Journal of Applied Chemistry》2007,80(3):405-418
Perfluoroolefins react with isopropyl alcohol under the conditions of radical initiation to form partially fluorinated aliphatic alcohols. The reactions of these alcohols with hexafluoropropylene and compounds containing labile halogen atoms (in particular, with allyl bromide and epichlorohydrin) were studied. 相似文献
5.
《Angewandte Chemie (International ed. in English)》2017,56(12):3237-3241
An Ir‐catalyzed intermolecular asymmetric dearomatization reaction of β‐naphthols with allyl alcohols or allyl ethers was developed. When an iridium catalyst generated from [Ir(COD)Cl]2 (COD=cyclooctadiene) and a chiral P/olefin ligand is employed, highly functionalized β‐naphthalenone compounds bearing an all‐carbon‐substituted quaternary chiral center were obtained in up to 92 % yield and 98 % ee . The direct utilization of allyl alcohols as electrophiles represents an improvement from the viewpoint of atom economy. Allyl ethers were found to undergo asymmetric allylic substitution reaction under Ir catalysis for the first time. The diverse transformations of the dearomatized product to various motifs render this method attractive. 相似文献
6.
With the aid of selected examples an overview is given of the development trends in highly discriminative reactions using organoaluminum compounds. (1) Isomerization of substituted oxiranes into allyl alcohols has been effected both stereo- and regioselectively by means of a new organoaluminum reagent, diethylaluminum 2,2,6,6-tetramethylpiperidide (DATMP); this reaction which provides a new route for the regiospecific transformation of allyl alcohols into 1,3-dienes. (2) A novel nonenzymic heterolysis of allylic phosphates of terpenoids has been effected by organoaluminum compounds and has enabled development of a new method for the selective synthesis of cyclic terpenes. (3) The reductive condensation of α-haloketones with carbonyl compounds in the presence of diethylaluminum chloride and zinc affords β-hydroxy-carbonyl derivatives in good yields with exclusion of undesired self-condensations products. 相似文献
7.
Highly reactive allyl(dialkyl)-, crotyl(dialkyl)-, 3,3-dimethylallyl(dialkyl)-(= prenyl(dialkyl), and diallyl(alkyl)-boranes were prepared by allylation of esters R2BOR′, RB(OR′)2 or thioesters R2BSR′ (R = alkyl) using allylic derivatives of aluminium, magnesium or boron in exchange reactions.The titled compounds are stable up to 100°C and do not symmetrize even on heating at 100°C for a long time. PMR spectroscopy data show that the characteristic feature of these compounds is a permanent allyl rearrangement, the rate of which increases with an increase in temperature. For allyl(diethyl)-borane at 100°C and 125°C the rates are equal to 2500 and 5000 sec?1 respectively; activation energy of the rearrangement amounts to 11.8±0.2 kcal mol?1.The boronallyl bonds in unsymmetrical allyl(alkyl)boranes readily split under the action of water and alcohols, protonolysis being accompanied by allyl rearrangement, crotyl and prenyl compounds are converted into 1-butene or 3-methyl-1-butene, respectively. 相似文献
8.
9.
Masanari KimuraRyutaro Mukai Naoko TanigawaShuji Tanaka Yoshinao Tamaru 《Tetrahedron》2003,59(39):7767-7777
Without prior activation of allyl alcohols, allylation of a variety of active methylene compounds with allyl alcohols proceeds smoothly at rt-50°C in the presence of catalytic amounts of Pd(OAc)2 (1-10 mol%), Et3B (30-240 mol%), a phosphine ligand (1-20 mol%), and a base (0 to 50-60 mol%). 相似文献
10.
Enrique Alvarez-Manzaneda Rachid ChahbounEsteban Alvarez Ramón Alvarez-ManzanedaPedro E. Muñoz Fermín JimenezHanane Bouanou 《Tetrahedron》2011,67(46):8910-8917
α-Acetoxy aldehydes or α-acetoxy ketones can be efficiently synthesized by treating 2,3-epoxy primary alcohols with lead tetraacetate. The reaction, which proceeds with complete regio- and stereoselectivity facilitates the enantioselective synthesis of α-acetoxy carbonyl compounds from allyl alcohols, via Sharpless epoxidation. Cyclic β-hydroxy ethers, with an oxygenated five-, six- or seven-membered ring, are transformed into α-acetoxy ethers. 相似文献
11.
E. Dbritz 《Angewandte Chemie (International ed. in English)》1966,5(5):470-477
The CuCl2-catalysed addition of alcohols to aliphatic caribodiimides (particularly diisopropylcarbodiimide) to form O,N,N′-trialkylisoureas may, in the case of bifunctional hydroxy compounds (esters of α-hydroxycarboxylic acids, diols, halogeno alcohols, amino alcohols, and cyclic hydroxy ethers), continue to give 5-, 6-, and 7-membered 1,3-O,N or 1,3-N,N heterocycles. O,N,N′-Trialkylisoureas are selective alkylating agents. Thus alcohols with allyl structures can be etherified with diisopropylcarbodiimide; a new method of esterification via O,N,N′-trialkylisoureas has been applied to mesitylenecarboxylic acid. 相似文献
12.
Jimmy A. van Rijn Marieke C. Guijt Dwight de Vries Elisabeth Bouwman Eite Drent 《应用有机金属化学》2011,25(3):212-219
The scope of the dehydrative allylation reaction using allyl alcohol as allyl donor with [RuCp(PP)]+ complexes as catalysts is explored. Aliphatic alcohols are successfully allylated with allyl alcohol or diallyl ether, obtaining high selectivity for the alkyl allyl ether. The reactivity of aliphatic alcohols is in the order of primary > secondary ? tertiary. The tertiary alcohol 1‐adamantanol reacts extremely slowly in the absence of strong acid, but when HOTs is added, reasonable yields of 1‐adamantyl allyl ether are obtained. The alkyl allyl ether is found to be the thermodynamically favored product over diallyl ether. Apart from alcohols, thiols and indole are also efficiently allylated, while aniline acts as a catalyst inhibitor. Allylation reactions with various substituted allylic alcohols give products with retention of the substitution pattern. It is proposed that a Ru(IV) σ‐allyl species plays a key role in the mechanism of these allylation reactions. Copyright © 2010 John Wiley & Sons, Ltd. 相似文献
13.
Various alkynes reacted with allyl tosylates in the presence of palladium catalysts, giving polysubstituted benzenes with good to high regioselectivity. Pentasubstituted and trisubstituted benzenes were readily prepared by reaction of internal alkynes and terminal alkynes, respectively. The combination of allyl alcohols and p-toluenesulfonic anhydride could be utilized in place of isolated allyl tosylates. The cyclization of diynes with allyl tosylate afforded bicyclic compounds containing an aromatic ring. 相似文献
14.
《Journal of organometallic chemistry》1987,322(2):177-183
The use of aqueous neutral media leads to excellent yields of homoallylic alcohols from reaction sof allyl halides with carbonyl compounds in the presence of tin or zinc. The stereochemical course and range of application of this reaction have been investigated. 相似文献
15.
《Tetrahedron: Asymmetry》2006,17(8):1290-1295
Acetovanillone has been used as the starting material for the synthesis of a series of secondary alcohols, which were resolved by lipase catalyzed esterification. 1-(4-Benzyloxy-3-methoxyphenyl)ethanol was efficiently resolved using immobilized lipase B from Candida antarctica (Novozym 435, CAL-B), whereas immobilized lipase A from C. antarctica (Novozym 735, CAL-A) was the lipase of choice for the resolution of the corresponding 2-bromo- and 2-chloro-derivatives. The enantioenriched alcohols are new building blocks for potential use in the synthesis of bioactive compounds. 相似文献
16.
Stéphane Malfait Richard Plantier-Royon Charles Portella 《Journal of fluorine chemistry》2011,132(10):760-766
A series of highly fluorinated compounds bearing two or four perfluoroalkyl (RF) chains, with a flexible or rigid core have been synthesized. Radical additions, nucleophilic addition or condensation reactions were implemented for these synthesis, using perfluoroalkylated iodides and alcohols and various type of substrates: bis(allylic) derivatives, epichlorhydrin, diacid derivatives. All compounds contain an unsaturated moiety (vinyl, allyl or internal double bond) to be grafted on silicone materials by a catalyzed hydrosilylation reaction. 相似文献
17.
《Tetrahedron》1987,43(17):3903-3915
Treatment of alkyl allyl carbonates with a phosphine-free palladium catalyst in acetonltrile affords ketones or aldehydes in high yields. This new method of oxidation of alcohols via allyl carbonates can be applied to various alcohols except simple primary alcohols. The reaction proceeds under neutral conditions and hence various acid- or base-sensitive functional groups are not affected during the reaction. Ruthenium hydride complex is also an effective catalyst. Direct dehydrogenatlon of secondary or allylic alcohols was carried out by the reaction with allyl methyl carbonate by the catalysis of the ruthenium complex. 1,4-Diols and 1,5-diols are converted to lactones with excess allyl methyl carbonate. 相似文献
18.
Zhan ZP Yang WZ Yang RF Yu JL Li JP Liu HJ 《Chemical communications (Cambridge, England)》2006,(31):3352-3354
A general and efficient BiCl3-catalyzed substitution reaction of propargylic alcohols with carbon and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols and amides, leading to the construction of C-C, C-O, C-S and C-N bonds, has been developed. 相似文献
19.
Zhan ZP Yu JL Liu HJ Cui YY Yang RF Yang WZ Li JP 《The Journal of organic chemistry》2006,71(21):8298-8301
A general and efficient FeCl3-catalyzed substitution reaction of propargylic alcohols with carbon- and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides, leading to the construction of C-C, C-O, C-S and C-N bonds, has been developed. 相似文献
20.
以甲基咪唑(或咪唑)和N-取代芳基-3-氯丙酰胺为原料,与KPF-6经离子交换制得6个新型酰胺基功能化离子液体(2a~2c和3a~3c)。以2-溴-6-甲氧基萘与烯丙醇反应为模板反应,2或3为反应介质,考察反应的转化率和区域选择性。结果表明: 3为反应介质时,转化率和区域选择性均高于2。以溴代芳烃和烯丙醇为原料,3c为反应介质,醋酸钯催化Heck反应制得2-取代芳烃烯丙醇化合物,收率85%~89%,立体选择性均大于99%。所得产物的结构均经1H NMR, 13C NMR, IR, EI-MS和元素分析表征。 相似文献