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1.
N. G. Kozlov L. A. Popova T. K. Vyalimyaé G. V. Nesterov V. O. Knizhnikov Yu. K. Ol'dekop 《Chemistry of Natural Compounds》1988,24(6):686-690
On the interaction of isocamphanone with butyllithium, 2-butyl-5,5,6-trimethylbicyclo[2.2.1]heptan-endo-2-ol is formed stereospecifically.
As a result of skeletal rearrangements of carbonium ions taking place in the course of the reaction, the Ritter reaction of
this tertiary alcohol with acetonitrile and benzonitrile has given endo-3-butyl-1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-ylacylamines
and endo-6-butyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylacylamines.
Institute of Physical Organic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk. Translated from Khimiya Prirodynkh
Soedinenii, No. 6, pp. 807–812, November–December, 1988. 相似文献
2.
S. S. Koval’skaya N. G. Kozlov E. A. Dikusar 《Russian Journal of Organic Chemistry》2005,41(6):832-837
2-(Phenylethynyl)isoborneol was synthesized by treatment of camphor with lithium phenylacetylide. Skeletal rearrangements of the title compound under the Ritter reaction conditions afforded a mixture of N-(4-phenylethynyl- and 4-benzoylmethyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)acetamides at a ratio of 8:3. The reaction of 2-(phenylethynyl)isoborneol with formic acid involved mainly Meyer-Schuster rearrangement instead of the expected Rupe rearrangement, and the major product was 2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)-1-phenylethanone. The minor product (∼6%) was 1-(2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-2-phenylethanone. The Ritter reaction of 2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)-1-phenylethanone selectively yielded N-(4-benzoylmethyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)acetamide.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 6, 2005, pp. 853–858.Original Russian Text Copyright © 2005 by Koval’skaya, Kozlov, Dikusar. 相似文献
3.
N. F. Bondar' S. S. Koval'skaya R. V. Skupskaya F. S. Pashkovskii E. A. Dikusar N. G. Kozlov F. A. Lakhvich 《Russian Journal of Organic Chemistry》2001,37(1):23-28
endo-2-Ethynyl-1,7,7-trimethylbicyclo[2.2.1]heptan-exo-2-ol reacts with nitrile oxides, yielding endo-2-(3-R-isoxazol-5-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-exo-2-ols. Treatment of the latter with methanesulfonyl chloride in pyridine leads to dehydration and formation of mixtures of the corresponding 1-(3-R-isoxazol-5-yl)-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptanes and 2-(3-R-isoxazol-5-yl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-enes at a ratio of 2:1. 相似文献
4.
Palomo C Oiarbide M Sharma AK Gonzalez-Rego MC Linden A Garcia JM Gonzalez A 《The Journal of organic chemistry》2000,65(26):9007-9012
(1R)-2-endo-Bromoacetyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (endo-2-bromoacetylisoborneol) 4 and its trimethylsilyl ether 3 are presented as efficient reagents for the asymmetric Darzens reaction. From the alpha,beta-epoxy ketone adducts the chiral inductor camphor is removed, by treatment with ceric(IV) ammonium nitrate, to yield the corresponding epoxy acids which are isolated as their dicyclohexylammonium salts. 相似文献
5.
S. S. Koval’skaya N. G. Kozlov E. A. Dikusar 《Russian Journal of Organic Chemistry》2010,46(8):1121-1134
Three-component condensation of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde with naphthalen-1-amine and cyclic β-diketones gave 7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydro-7H-benzo[c]acridin-8-one derivatives possessing three or more asymmetric carbon atoms. Steric factors were found to be responsible for
the predominant formation of the (7R)-isomers (R/S ≈ 7: 5) and orientation of substituents in the cyclohexenone fragment. The same factors determined complete regioselectivity
of the reaction with methyl 2,4-dioxocyclohexane-1-carboxylates as dicarbonyl component, which led to exclusive formation
of methyl 8-oxobenzoacridine-11-carboxylates. In the reaction of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde with naphthalen-1-amine and barbituric acid as dicarbonyl component,
the only product was that formed by two-component condensation of barbituric acid with bicyclic aldehyde. 相似文献
6.
Khalid A. Al-Farhan Ismail Warad Saud I. Al-Resayes Moustafa M. Fouda Mohamed Ghazzali 《Central European Journal of Chemistry》2010,8(5):1127-1133
Borneol is a monoterpene that is a part of traditional Chinese and Japanese medicine. (−) borneol reacted with methanesulfonyl
chloride in THF/pyridine to afford the new 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate derivative in excellent
yield. The product is characterized by H1NMR, C13NMR, mass spectroscopy as well as elemental analysis and its structure was identified by X-ray single crystal diffraction.
The packing of 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methanesulfonate exhibits the non-classical C-H···O hydrogen bonding
in C(4) and R2
2(8) chain and ring motifs as structural determinants. This was also confirmed by the analysis of Hirshfeld surfaces. The 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl
methane sulfonate antimicrobial activity was tested and compared with its parent (−) borneol against three different pathogens.
Particularly, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate showed high sensitivity, compared to Chloramphenicol
reference material, against Escherichia coli.
相似文献
7.
8.
E. V. Buravlev I. Yu. Chukicheva K. Yu. Suponitsky A. V. Kutchin 《Russian Journal of General Chemistry》2013,83(7):1345-1348
Di(4-hydroxy-2-{(1R*,2S*,4S*)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl}-6-{(1S*,2R*,4R*)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl})methane was synthesized by condensation of the meso-diastereomer of 2,6-diisobornylphenol with paraformaldehyde under acid catalysis. The product structure as a meso-forms was confirmed by XRD analysis. 相似文献
9.
S. Munavalli D. K. Rohrbaugh H. D. Durst 《Phosphorus, sulfur, and silicon and the related elements》2013,188(11):2989-2995
Thiocamphor has been found to furnish bornane, camphor, isoborneol, isobornylthiol, bornylthiol, tetrahydro-bis-(1,7,7-trimethylbicyclo[2.2.1]heptyl)-3,3′-disulfide, and three isomeric bis-(1,7,7-trimethylbicyclo[2.2.1]heptyl)-3,3′-dithiols when treated with NaBH4 either in dry THF or dry diethylene glycol diethyl ether. The origins of the above interesting compounds and their mass spectral characterization are presented in this article. 相似文献
10.
I. Yu. Chukicheva L. V. Spirikhin A. V. Kuchin 《Russian Journal of Organic Chemistry》2008,44(1):62-66
The alkylation of phenol with camphene in the presence of boron trifluoride in glacial acetic acid was accompanied by tandem molecular rearrangement with formation of a mixture of ortho- and para-substituted phenols having 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl and 5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl substituents. The same products were obtained by rearrangement of 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yloxybenzene under analogous conditions. Similar reactions performed in the presence of aluminum phenoxide as catalyst resulted in predominant formation of the corresponding ortho-substituted phenols. 相似文献
11.
Hedin-Dahlström J Rosengren-Holmberg JP Legrand S Wikman S Nicholls IA 《The Journal of organic chemistry》2006,71(13):4845-4853
[structures: see text] A class II aldolase-mimicking synthetic polymer was prepared by the molecular imprinting of a complex of cobalt (II) ion and either (1S,3S,4S)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4a) or (1R,3R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4b) in a 4-vinylpyridine-styrene-divinylbenzene copolymer. Evidence for the formation of interactions between the functional monomer and the template was obtained from NMR and VIS titration studies. The polymers imprinted with the template demonstrated enantioselective recognition of the corresponding template structure, and induced a 55-fold enhancement of the rate of reaction of camphor (1) with benzaldehyde (2), relative to the solution reactions, and were also compared to reactions with a series of reference polymers. Substrate chirality was observed to influence reaction rate, and the reaction could be competitively inhibited by dibenzoylmethane (6). Collectively, the results presented provide the first example of the use of enantioselective molecularly imprinted polymers for the catalysis of carbon-carbon bond formation. 相似文献
12.
A. V. Bogdanov V. F. Mironov N. R. Khasiyatullina D. B. Krivolapov I. A. Litvinov A. V. Kuchin A. I. Konovalova 《Russian Chemical Bulletin》2006,55(2):396-398
The reaction of 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione with hexaethyltriamido-phosphite in the presence of diethylammonium
chloride afforded a stable quasiphosphonium salt, viz., (1,7,7-trimethyl-2-oxobicyclo[2.2.1]hept-3-yloxy)tris(diethylamino)phosphonium chloride, as one diastereomer (racemate,
1R*,3S*,4S*).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 383–385, February, 2006. 相似文献
13.
L. R. Khalitova A. V. Antipin S. A. Grabovskii N. N. Kabal’nova 《High Energy Chemistry》2018,52(5):446-448
The yield of singlet oxygen (1О2) in the decomposition of a number of hydrotrioxides of alcohols (cyclobutanol, cyclopentanol, cyclohexanol, cycloheptanol, cyclooctanol, L-menthol, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol, heptan-4-ol, propanol-2, and 1-cyclopropylethanol) has been determined using the IR chemiluminescence technique. It has been shown that cyclopentanol, 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol and 1-cyclopropylethanol hydrotrioxides are efficient sources of singlet oxygen; the yield of 1О2 reaches up to 58%. 相似文献
14.
《Tetrahedron: Asymmetry》2006,17(1):79-91
Reductions of (1R,3R,4R)-3-([1,2,4]triazolo[4,3-x]azin-3-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and their lactone analogues, prepared from (1R)-(+)-camphor, were studied. Catalytic hydrogenation selectively led to partial saturation of the [1,2,4]triazolo[4,3-x]azine residue, while in reactions with borane–methylsulfide coordination of borane to the 1-position of [1,2,4]triazolo[4,3-x]azine system took place. On the other hand, activation of the carbonyl group in (1R,3R,4R)-3-([1,2,4]triazolo[4,3-x]azin-3-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones with boron trifluoride etherate followed by reaction with borane–methylsulfide furnished the corresponding isoborneols, stereoselectively. The structures of all representative compounds were confirmed by X-ray diffraction. 相似文献
15.
16.
Density functional theory (DFT) calculations at B3LYP/6-31G(d,p) level were carried out to investigate the mechanism of the reaction of benzaldehyde (BA) or acetaldehyde (AD) with (1R)-2-endo-bromoacetyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (endo-2-bromoacetylisoborneol) 1 (Scheme 1). The calculations indicate that the reactions are diastereoselective, in good agreement with the experimental results [1]. Moreover, the calculations show that these reactions proceed via two steps: (1) an aldol-like reaction and (2) the formation of an epoxide. Our calculation study of the transition states demonstrates that the terminal hydroxyl group in compound 1 is vital for the stereoselectivity of the reactions. 相似文献
17.
手征性cis-β-亚磺酰丙烯酸酯可从(1R, 2S, 3R)-3-巯基-1,7,7-三甲基二环[2.2.1]庚-2-醇制备, 它与环戊二烯的反应得Diels-Alder加成物, 并具有相当高的端基差向异构选择性。 相似文献
18.
M. N. Aboul-Enein A. A. EL-Azzouny Y. A. Maklad Y. S. Sokeirik H. Safwat 《Journal of the Iranian Chemical Society》2006,3(2):191-208
Starting from (1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylideneamino)-acetic acid methyl esters 6a, 6b, the aryl esters of exo-2-[methyl-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amino]-ethanol (10a-f) and exo-2-[methyl-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amino-2-phenyl-ethanol (10g-n) are prepared. Also, from the reaction of 1,7,7-trimethyl-bicyclo[2.2.1]heptan nitramine 4 with either 2-amino-1-(4-nitrophenyl)-propane-1,3-diol (17) or 1-aminomethyl-cyclohexanol (18), the alcohol exo-1-[(1,7,7-trimethyl-bicylo[2.2.1]hept-2-ylamino)-methyl]-cyclohexanol (13), exo-1-(4-aminophenyl)-2-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylamino)-propane-1,3-diol (14) and 1-(4-aminophenyl)-2-[methyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-amino]-propane-1,3-diol (16) are synthesized. At a dose level of 12.5 mg/kg, compounds 16 and 14 show a significant anticonvulsant protection against pentylenetetrazole seizures (100% and 83% protection, respectively) compared with diphenylhydantoin sodium (50 mg/kg, 100%) and deramciclane fumarate (25 mg/kg, 83%), used as reference drugs. Compound 10b at dose level of 50 mg/kg displayed 41%, hypoglycemic activity, compared with gliclazide (10 mg/kg, 23%) as reference drug. Furthermore, the prepared compounds are screened for their anti-inflammatory potential at a dose level of 50 mg/kg. Compounds 10i, 10g, 14 and 10m exhibited 92%, 90%, 88% and 80% inhibition in rat paw weight, respectively, with no sign of ulcerogenicity, compared with indomethecin (5 mg/kg, 81%). 相似文献
19.
Kuvshinov G. V. Surovegin A. V. Bakanov M. O. Maslov A. V. 《Russian Journal of General Chemistry》2021,91(12):2606-2612
Russian Journal of General Chemistry - Surface modification of the diatomite adsorbent Hezasorb AW-HMDS by tetra(1,7,7-trimethylbicyclo[2.2.1]heptane[2,3-b]pyrazino)porphyrazine Pd(II) was... 相似文献
20.
Paul G. Gassman Kentaro Okuma Aline Lindbeck Richard Allen 《Tetrahedron letters》1986,27(52):6307-6310
-2,3-Epoxy-1,7,7-trimethylbicyclo[2.2.1]heptane reacted with trimethylsilyl cyanide in the presence of zinc iodide to produce a complex mixture of products. The major product,
-7-trimethylsiloxy-
-2,3,3-trimethyl-
-2-isocyanobicyclo[2.2.1]heptane was obtained in 72% yield. In addition, eight other products were identified in yields ranging from 10% to 1%. All of the products could be rationalized on the basis of initial generation of a carbocationic intermediate. 相似文献