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1.
1,4-苯并二氧六环木脂素类天然产物多数具有增加胆碱乙酰化酶和抗肝毒等活性 ,其活性主要源于 1 ,4-苯并二氧六环官能团 [1] . 1 ,4-苯并二氧六环木脂素的消旋全合成已有报道 [2 ] ,但其不对称合成还是空白[3] .我们发展了一条对映选择性合成 1 ,4-苯并二氧六环木脂素的简捷有效的路线 .基于前面的工作 [4 ] ,我们发现 1 ,4-苯并二氧六环醛类衍生物是合成此类天然产物的关键中间体 ,选择 2 - (4-羟基- 3-甲氧基 ) - 3-羟甲基 - 1 ,4-苯并二氧六环 - 6-醛 (1 )作为目标分子 ,其合成路线如下 :Reagents and conditions:( ) Me OH,H2 SO4,9… 相似文献
2.
Hu Yi Zhang Zhen Jun Yang Hong Wu Yu Zhi Song Piao Ling Tai Ma Ji Mei Min 《合成通讯》2013,43(23):4113-4126
The syntheses of 2-(4-aminocarbonyl-2-thiazoyl)-1,4-anhydro-D-ribitol 10 and 2-(4-aminocarbonyl-2-thiazoyl)-1,4-anhydro-D-arabitol 11 have been accomplished via the construction of thiazoyl moiety from the cyanohydrins 2 and 3. 相似文献
3.
T. V. Mikhalina S. V. Rubashko E. P. Fokin I. Yu. Bagryanskaya Yu. V. Gatilov 《Russian Chemical Bulletin》1995,44(12):2346-2349
It was shown that the reaction of 2-chloro-3-(4-N,N-dimethylaminoanilino)-1,4-naphthoquinone with piperidine in the absence of a solvent gives not only a product of replacement of the chlorine atom by a piperidino group, 3-(4-N,N-dimethylaminoanilino)-2-piperidino-1,4-naphthoquinone, but also 2-(4-N,N-dimethylaminoanilino)-1,4-naphthoquinone and 2-(4-N,N-dimethylaminoanilino-2-piperidino)-1,4-naphthoquinone. The latter compounds are the only reaction products formed in dimethyl sulfoxide. The reaction with morpholine occurs in a similar way, whereas that with pyrrolidine gives only a product of replacement of the chlorine atom by hydrogen.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2451–2454, December, 1995. 相似文献
4.
5.
A systematic study has been carried out on the three isomeric cyclohexanedicarboxylates (CHDCs) formed by cadmium and manganese with the three isomeric dicarboxylic acids, in the presence or absence of amines. The CHDCs have been prepared under hydrothermal conditions and their structures established by X-ray crystallography. We have been able to isolate two-dimensional layered structures of 1,2-, 1,3- and 1,4-cyclohexanedicarboxylates and chain structures of 1,3- and 1,4-cyclohexanedicarboxylates. The infinite metal-oxygen-metal linkages are observed only in the case of the 1,2-dicarboxylate. In all the three isomeric cyclohexanedicarboxylates, the e,e conformation is most favored, although the 1,4-CHDCs often contain rings in both the e,e and the a,e conformations. 相似文献
6.
Ippolito Antonini Francesco Claudi Gloria Cristalli Mario Grifantini Sante Martelli 《Journal of heterocyclic chemistry》1980,17(1):181-185
The course of the thermal, acid-catalysed and iodide-catalysed decomposition of 2-amino-3-(2′,2′-dimethylaziridino)-1,4-naphthoquinone (III) was investigated. Thermal and iodide-catalysed decompositions gave mainly 2,3-diamino-1,4-naphthoquinone (VI) and 2-amino-3-(2′-methylallylamino)-1,4-naphthoquinone (V) together with low amounts of 2,2-dimethyl-1,2,3,4,5,10-hexahydrobenzo[g]quinoxaline (IV) and 2-isopropyl-1H-naphthoimid-azole-4,9-dione (VII). The acid catalysed isomerization of the aziridinonaphthoquinone III with halohydric acids or with acetic acid readily gave the opening of the aziridine ring; the corresponding salts of 2-amino-3-(2′-haloisobutylamino)-1,4-naphthoquinones (VIIIa-c) and 2-amino-3-(2′-acetoxyisobutylamino)-1,4-naphthoqunone (X) were formed by cleavage of the carbon-nitrogen bond at the substituted carbon atom. Hypotheses on the mechanism of these reactions are given. 相似文献
7.
8.
《Polyhedron》1987,6(5):1059-1064
The reactions of palladium(II) chloride with 1,4 - diphenyl - 2,3 - dimethyl - 1,4 - diazabutadiene and 1,4 - di(p - methoxyphenyl) - 2,3 - dimethyl - 1,4 - diazabutadiene are described. With 1,4 - diphenyl - 2,3 - dimethyl - 1,4 - diazabutadiene diimine fission is produced, giving rise to a product identified by elemental analysis, IR and Raman spectra, and X-ray diffraction, as trans-dichlorobis(aniline) palladium(II). The complex is soluble in dimethylformamide and crystallizes with two molecules of solvent. The substance crystallizes in the monoclinic space group P21/n. The X-ray data were refined to R = 0.047 and Rw = 0.046. Final distances are PdN = 2.060(5)Åand PdC1 = 2.299(2)Å. There are two bifurcated intermolecular NH ... C1 and CH... C1 hydrogen bonds which, together with one more intermolecular hydrogen bond NH... O, are responsible for the packing of the molecules. However, when 1,4 - di(p - methoxyphenyl) - 2,3 - dimethyl - 1,4 - diazabutadiene was treated with palladium chloride under the same conditions cis - dichloro - 1,4 - di(p - methoxyphenyl) - 2,3 - dimethyl - 1,4 - diazabutadiene was formed, as deduced from elemental analysis, and IR and Raman spectra. 相似文献
9.
Rotational isomers (rotamers) of the three structural isomers of benzenedicarboxaldehydes (1,2-, 1,3-, and 1,4-derivatives) have been investigated in detail using matrix-isolation infrared spectroscopy in the 600-4000 cm-1 region, combined with UV photoexcitation and density-functional theory (DFT) calculations. Two rotamers were identified for 1,2- and 1,4-benzenedicarboxaldehyde (1,2- and 1,4-BDA, respectively), while three rotamers were identified for 1,3-benzenedicarboxaldehyde (1,3-BDA) in infrared spectra upon UV-irradiation. Most of the observed infrared bands of each rotamer have been assigned. The energetic relationships among the rotamers were revealed based on the infrared data and the DFT calculations. It is shown that the intramolecular C-H...H-C interaction in the H-syn rotamer or the C-H...O=C hydrogen bonding in the anti rotamer of 1,2-BDA results in the blue-shift of the aldehyde C-H stretching band and the shortening of the aldehyde C-H bond length. Both photoinduced rotational isomerization and rearrangement were observed upon UV irradiation for 1,2-BDA. The structure of the major enol isomer formed as the result of the photochemical rearrangement of 1,2-BDA is determined. 相似文献
10.
V. V. Shchepin D. V. Uzun Yu. G. Stepanyan P. S. Silaichev M. I. Vakhrin 《Russian Journal of Organic Chemistry》2007,43(7):995-997
Zinc enolates derived from 1-aryl-2,2-dibromoalkanones reacted with tetramethyl 2,2′-(1,4-phenylenedimethylidene)dimalonate, dimethyl 3,3′-(1,4-phenylene)bis(2-cyanoacrylate), and 2,2′-(1,4-phenylenedimethylidene)bis(malononitrile) to give, respectively, tetramethyl 3,3′-(1,4-phenylene)bis(2-alkyl-2-aroylcyclopropane-1,1-dicarboxylates), dimethyl 3,3′-(1,4-phenylene)bis(2-alkyl-2-aroyl-1-cyanocyclopropane-1-carboxylates), and 3,3′-(1,4-phenylene)bis(2-alkyl-2-aroylcyclopropane-1,1-dicarbonitriles) as a single stereoisomer. 相似文献
11.
1,4 - Dimethyl - 2 - nitro - 3 - phenylsulphonylnaphthalene (2) reacts with sodium benzenethiolate in DMSO at 120° to give 1 - methyl - 2 - nitro - 4 - phenylthiomethylnaphthalene (4) [tele-substitution product (TSP) of the phenylsulphonyl group] and 1,4 - dimethyl - 3 - phenylsulphonyl - 2 - phenylthionaphthalene (5) [normal substitution product (NSP) of the nitro group]. The analogous reactions of 2 with sodium 2,4,6- trimethylbenzenethiolate and of 2,3 - bisphenylsulphonyl -1,4 - dimethylnaphthalene (3) with sodium benzenethiolate or aliphatic amines give only TSPs of the phenylsulphonyl group. In the case of the reaction of 2 with aliphatic amines both the possible TSPs (tele-substitution of the phenylsulphonyl or of the nitro group) were isolated in 9:1 relative yield. All the data show that the phenylsulphonyl is a leaving group far better than the nitro in such tele-substitution processes. The mechanism previously proposed to account for the formation of TSPs from 1,4-dimethyl - 2,3 - dinitronaphthalene is strongly supported by the obtained results. 相似文献
12.
A. E. Devyashina L. M. Gornostaev Yu. V. Gatilov 《Russian Journal of Organic Chemistry》2012,48(2):234-240
Reactions of 2-(4-hydroxyarylamino)-1,4-naphthoquinones with cerium ammonium nitrate or pyridinium chlorochromate depending
on the structure of initial substrate and the type of reagent led to the formation of 2-chloro-3-(4-cyclohexa-2,5-dienylideneamino)-1,4-dihydronaphthalene-1,4-diones,
2-(4-hydroxy-3-nitrophenylamino)-1,4-naphthaquinones, and also to simultaneous oxidation and chlorination. 相似文献
13.
B. S. Thyagarajan K. C. Majumdar Dallas K. Bates 《Journal of heterocyclic chemistry》1975,12(1):59-66
The mercuric ion-catalyzed hydration of 1,4-bis(arylthio)-2-butynes and 1-aryloxy-4-arylthio-2-butynes was studied. The 1,4-bis(arylsulfonyl)-2-butynes afforded 1,4-bis(arylsulfonyl)-2-butanones (7). The 1,4-bis(arylthio)-2-butynes afforded a variety of products in acetic acid among which were: 1,4-bis(arylthiomethyl)vinyl acetate ( 18 ); 1,4-bis(arylthio)-2-butanone ( 15 ); 1-(arylthio)-3-buten-2-one ( 16 ); and 1-(arylthio)-4-acetoxy-2-butanone ( 17 ). Ketone 15 eliminates arylthiol in an acidic medium yielding 16 which undergoes Michael addition of solvent to give 17. Treatment of 7 with base in the presence of a nucleophile (ArSH) analogously leads to elimination of arylsulfinic acid, followed by Michael addition of arylthiol. Hydration of 5 in methanol cleanly gave 1-(arylthio)-4-methoxy-2-butanones ( 19 ). In contrast, 1-aryloxy-4-arylthio-24)utynes afforded chromenes ( 8 ) by intramolecular cyclization. No thiochromenes were formed in any of the examples investigated. 相似文献
14.
Andrew J. Peloquin Srikar Alapati Colin D. McMillen Timothy W. Hanks William T. Pennington 《Molecules (Basel, Switzerland)》2021,26(16)
Through variations in reaction solvent and stoichiometry, a series of S-diiodine adducts of 1,3- and 1,4-dithiane were isolated by direct reaction of the dithianes with molecular diiodine in solution. In the case of 1,3-dithiane, variations in reaction solvent yielded both the equatorial and the axial isomers of S-diiodo-1,3-dithiane, and their solution thermodynamics were further studied via DFT. Additionally, S,S’-bis(diiodo)-1,3-dithiane was also isolated. The 1:1 cocrystal, (1,4-dithiane)·(I2) was further isolated, as well as a new polymorph of S,S’-bis(diiodo)-1,4-dithiane. Each structure showed significant S···I halogen and chalcogen bonding interactions. Further, the product of the diiodine-promoted oxidative addition of acetone to 1,4-dithiane, as well as two new cocrystals of 1,4-dithiane-1,4-dioxide involving hydronium, bromide, and tribromide ions, was isolated. 相似文献
15.
Rakesh Kumar Gueijun Ji Leonard I. Wiebe Edward E. Knaus 《Journal of heterocyclic chemistry》1991,28(3):711-715
5-Iodo-3′-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl)-2′-deoxyuridine (15a) , 5-vinyl-3′-O-(1-methyl-1,4-di-hydropyridyl-3-carbonyl)-2′-deoxyuridine (15b) and (E)-5-(2-iodovinyl)-3′-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl)-2′-deoxyuridine (15c) were synthesized for future evaluation as lipophilic brain-selective antiviral agents for the treatment of herpes simplex encephalitis. Quaternization of the 3′-O-(3-pyridylcarbonyl) compounds 10–11 using iodomethane afforded the corresponding 1-methylpyridinium salts 12–13 which were reduced with sodium dithionite to yield the corresponding 3′-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl) compounds 14–15. 相似文献
16.
Pushpakumar K. Varalakshmi M. Sankar A. Uma Ravi Naidu Reddi Mohan Umamahesh K. Reddy D. Venkataramana Raju C. Naga 《Russian Journal of Organic Chemistry》2022,58(4):612-618
Russian Journal of Organic Chemistry - A series of new 1,1′-(1,4-phenylene)diurea derivatives were synthesized by reacting 1,4-diisocyanatobenzene with various biologically... 相似文献
17.
Fausto Ramirez Hikotada Tsuboi Hiroshi Okazaki James F. Marecek 《Tetrahedron letters》1982,23(51):5375-5376
1,3-, 1,4-, and 1,5-Alkanediols are converted into the corresponding 6-, 7-, and 8- membered cyclic phosphodiesters in a two-step procedure utilizing N-(1,2-dimethylethylene-dioxyphosphoryl)imidazole ( as the sole phosphorylating reagent. 相似文献
18.
L. L. Dmitrieva L. P. Nikitina A. I. Albanov N. A. Nedolya 《Russian Journal of Organic Chemistry》2005,41(10):1430-1444
Reactions of 2-(allyloxymethyl)- and 2-[2-(vinyloxy)ethoxy]methyloxiranes with 2-propynol (~3 wt % of t-BuOK, 75–85°C, 5–10 h) lead to formation of new 1-organyloxy-3-(2-propynyloxy)propan-2-ols (yield 65–95%). On heating to 45–100°C in the presence of bases (KOH, t-BuOK), 1-allyloxy- and 1-[2-(vinyloxy)ethoxy]-3-(2-propynyloxy)propan-2-ols are transformed into the corresponding 2-vinyl-1,3-dioxolane, 6-methyl-2,3-dihydro-1,4-dioxine, 6-methylene-1,4-dioxane, and 2,3-dihydro-5H-1,4-dioxepine derivatives, whose yield and ratio strongly depend on the solvent nature, catalyst, and substituent at the hydroxy group. 2-Vinyl-1,3-dioxolane and 6-methyl-2,3-dihydro-1,4-dioxine derivatives are formed as the major products (yield 70–99%) in the presence of t-BuOK in aprotic media (toluene, THF, DMSO) or in the absence of a solvent as a result of prototropic isomerization followed by intramolecular heterocyclization. Intramolecular nucleophilic cyclization of 3-(2-propynyloxy)propan-2-ols to 6-methylene-1,4-dioxane is the predominant process in water in the presence of KOH. In all cases, the fraction of 2,3-dihydro-5H-1,4-dioxepine derivatives among the cyclization products ranges from 0 to 5% (KOH) or to 14% (t-BuOK). 相似文献
19.
Elisa Leyva Lluvia I. López Margarita Rodríguez-Kessler 《Journal of fluorine chemistry》2011,132(2):94-140
The preparation of novel 2-(fluoroanilino)-1,4-naphthoquinones is presented. It takes place under mild conditions by reacting the corresponding fluoroaniline and 1,4-naphthoquinone in the presence of a Lewis acid catalyst with strong oxidation properties such as CeCl3·7H2O. This preparation was also investigated under microwave irradiation. All 1,4-naphthoquinone derivatives were characterized by UV-Vis, IR, 1H and 19F NMR, MS and cyclic voltammetry, to investigate the effect of the fluoro-substituents on their electronic properties. 相似文献
20.
A. P. Avdeenko V. V. Pirozhenko L. M. Yagupol''skii I. L. Marchenko 《Russian Journal of Organic Chemistry》2001,37(7):991-1000
Oxidation of N-(N-arylsulfonylimidoyl)-4-aminophenols gave the corresponding N-[N-arylsulfonylimidoyl)-1,4-benzoquinonimines, derivatives of N-aroyl- and N-acetyl-1,4-benzoquinonimines. The structure of the products was studied by the X-ray diffraction method and 1H and 13C NMR spectroscopy. N-(N-Arylsulfonylimidoyl)-1,4-benzoquinonimines were found to undergo fast (on the NMR time scale) Z
E isomerization about the CÍN bond in the quinonimine fragment. N-(N-Arylsulfonylacetimidoyl)-1,4-benzoquinonimines in solution give rise to dynamic Z
E-isomerization with respect to the CÍN bond in the N-arylsulfonylacetimidoyl fragment. 相似文献