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1.
V. N. Odinokov G. Yu. Ishmuratov I. M. Ladenkova G. A. Tolstikov 《Chemistry of Natural Compounds》1987,23(3):365-368
(Z)-hexadec-11-enal and (Z)-hexadec-11-1-yl acetate — components of the sex pheromone of insects of the generaHeliothis andManestra, respectively — have been synthesized by the condensation of undec-10-enal with hex-1-yne, deoxygenation of the heptadec-1-en-12-yn-11-ol formed via the corresponding tosylate to heptadec-1-en-12-yne, and the selective oxonolysis of the latter.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 440–444, May–June, 1987. 相似文献
2.
V. N. Odinokov G. Yu. Ishmuratov I. M. Ladenkova E. M. Vyrypaev G. A. Tolstikov 《Chemistry of Natural Compounds》1990,26(6):702-704
The selective ozonolysis of pentadec-1-en-12-yne and heptadec-1-en-12-yne, synthesized from the readily available undecylenic
acid, has given tetradec- and hexadec-11-yn-1-ols — acetylenic precursors of a number of pheromones of insects of the order
Lepidoptera.
Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya
Prirodnykh Soedinenii, No. 6, pp. 823–825, November–December, 1990. 相似文献
3.
V. N. Odinokov G. G. Balezina G. Yu. Ishmuratov R. Sh. Vakhitov G. A. Tolstikov 《Chemistry of Natural Compounds》1985,21(3):369-371
A new route for the synthesis of dec-5E- and -5Z-enyl acetates — the sex pheromones of the peach-tree borer and of the turnip moth — is proposed which is based on the two-stage hydroxyethylation of hex-1-yne using 2-chloroethyl vinyl ethers and ethylene oxide.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 395–398, May–June, 1985. 相似文献
4.
V. N. Odinokov G. Yu. Ishmuratov G. G. Balezina G. A. Tolstikov 《Chemistry of Natural Compounds》1985,21(3):372-374
A new route is proposed for the synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates which is based on the reaction of the Grignard reagent from the readily accessible 1-bromo-5-(1-ethoxyethoxy)pentane with 1-bromohept-3-yne — the bromide obtained from product of the -hydroxyethylation of pent-1-yne with 2-chloroethylvinyl ether, hept-3-yn-1-ol, by a double decomposition reaction of its tosylate with lithium bromide. The key synthon — dodec-8-yn-1-ol — was converted with the aid of sodium in liquid ammonia into the stereochemical individual dodec-8E-enol, while its reduction with the aid of 9-borabicyclo[3.3.1]nonane (BBN) gave the steroisomeric alcohol exclusively with the Z configuration, as followed from the results of capillary GLC and the IR spectra of the corresponding acetates. The PMR spectra of the compounds synthesized are also given.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 398–400, May–June, 1985. 相似文献
5.
V. N. Odinokov O. S. Kukovinets N. I. Sakharova G. A. Tolstikov 《Chemistry of Natural Compounds》1992,27(4):494-496
The synthesis has been effected of octa-2E,6E-diene-1,8-diol diisovalerate — the sex pheromone of the Crimean click beetleAgriotes tauricus — by the carboxymethylenation of the readily available 6-methylhept-5-en-2-one, the allyl oxidation of a terminal methyl group, reduction of the ester fraction, and interaction of the diol so obtained with isovaleryl chloride. The required pheromone can also be obtained from available cyclic oligomers of isoprene.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 565–568, July–August, 1991. 相似文献
6.
A. L. Veretenov A. S. Gybin V. A. Smit V. A. Chertkov A. S. Shashkov 《Russian Chemical Bulletin》1989,38(8):1725-1733
Dicobaltohexacarbonyl 4-methyl-pent-3-en-1-yne complexes have been acylated with acryloyl and crotonoyl tetrafluoroborates followed by methanolysis to make acylmethoxy adducts containing hem-dimethyl moieties. Conditions have been defined under which such adducts containing enone systems are selectively reduced to allyl acohols with retention of the cobaltocarbonyl moieties. The latter can be converted by Quand-Poson reaction to the inaccessible polyfunctional derivatives of 7,7-dimethylbicyclo[3.3.0]octane.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1879–1888, August, 1989. 相似文献
7.
V. N. Odinolov U. M. Dzhemilev G. Yu. Ishmuratov L. P. Botsman O. S. Vostrikova I. M. Ladenkova R. M. Sultanov N. A. Nagaeva G. A. Tolstikov 《Chemistry of Natural Compounds》1987,23(2):242-244
A synthesis of hexadec-9Z-enal — a component of the sex pheromone of the cotton boll-wormHeliothis armigera (Hübner) — based on cyclooctene (I) is proposed. Through a solution of 22 g of (I), 250 ml of cyclohexane, and 40 ml of MeOH is passed (at 5°C) 0.2 M O3/O2, the solution is decanted off, and the precipitated ozonide is dissolved in 200 ml of MeOH and is reduced with 19 g of NaBH4 (40°C) with the isolation, after the usual working up, of 23.4 g of octane-1,8-diol (II). From 0.5 mole of (II) and 0.6 mole of 45% HBr 8-bromooctan-1-ol (III) is obtained and this is converted into 1-(2-THPL)oxy)-8-bromooctane (IV). The condensation of (IV) with oct-1-yne (Ar, LiNH2, HMPTA, 10°C, 1 h, and then 55°C, 10 h) leads to 1-(2-THPL-oxy)hexadec-9-yne (V) the hydrolysis of which (MeOH, H2O, p-TsOH, 20°C for 20 h) yields hexadec-9-yn-ol (VI). The reduction of (VI) (Et2O, iso-BuMgBr, Cp2TiCl2, 0°C, 15 min, then 20°C, 1 h) yieldshexadec-9Z-en-l-ol (VII). The oxidation of (VII) (PyHCrO
3
+
Cl–, CH2Cl2, 20°C, 2 h) gives hexadex-9Z-enal (VIII). Characteristics of the compounds (yield (%), n
D
20
(25): (II) – 80, mp 61–62°C; (III) – 75, 1.4807; (IV) – 99, —; (V) – 52, 1,4650; (VI) – 85, 1.4657; (VII) – 99, 1.4650; (VIII) – 98, 1.4600. Characteristics of the IR and PMR spectra of compounds (V–VII) are given.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 286–289, March–April, 1987. 相似文献
8.
U. M. Dzhemilev G. G. Balezina L. A. Volkova V. P. Krivonogov G. A. Tolstikov 《Chemistry of Natural Compounds》1980,16(1):82-85
A new route to the synthesis of a number of attractants of Lepidoptera(Argyrotaenia velutinana, Mamestra configurata, andLycorea ceres ceres) have been developed. These substances are acetates of enols with the cis configuration: tetradec-11-en-1-ol, hexadec-11-en-1-ol, and octadec-11-en-1-ol, respectively. The constants of the substances obtained agree completely with those given in the literature. The method is based on the coupling of the C3, C5, and C7 aldehydes with methyl 11-bromoundecanoate (I) by the Wittig reaction. To obtain compound (I) from methyl undeca-2E,5E,10-trienoate or methyl undeca-10-enoate we used hydroboration according to Brown followed by hydrogenation and bromination of the alcohol obtained. The advantage of this method is the use as starting materials of esters of unsaturated acids readily obtained by the homogeneous catalytic co-oligomerization of 1,3-dienes with acrylates.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 97–102, January–February, 1980. 相似文献
9.
V. N. Odinokov 《Chemistry of Natural Compounds》2000,36(1):11-39
Syntheses of acetogenin pheromones using acetylene derivatives are reviewed.Institute of Petroleum Chemistry and Catalysis, Academy of Sciences of the Republic of Bashkortostan and Ufa Scientific Center, Russian Academy of Sciences, 450075, Ufa, pr. Oktyabrya, 141. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 12–31, January–February, 2000. 相似文献
10.
The synthesis has been performed of (14R)-15-acetoxyisoagath-12-en-16-al and of (14R)- and (14S)-isoagath-12-ene-15,16-dials, which are metabolites of the marine spongeSpongia officinalis, and alos of a number of substances related to them starting from (14R)- and (14S)-isoagath-12-en-15-ols.Institute of Chemistry, Academy of Sciences of the Moldavian SSR, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 45–51, January–February, 1985. 相似文献
11.
Da-Wei Chuang Mohamed El-Shazly Chin-Chau Chen Yu-Ming Chung Balaji D. Barve Ming-Jung Wu Fang-Rong Chang Yang-Chang Wu 《Tetrahedron letters》2013
1,5-Diphenylpent-3-en-1-yne derivatives were isolated in minor quantities from terrestrial plants and exhibited strong anti-inflammatory activity. A cross coupling reaction between B-benzyl-9-BBN and chloroenynes under mild condition was developed resulting in the formation of different 1,5-diphenylpent-3-en-1-yne derivatives with a full control on the E/Z selectivity. Several substrates bearing electron-donating and electron-withdrawing substituents were tolerable under the reaction conditions affording the corresponding products in good yields. This is the first study to report the synthesis of a vast array of novel 1,5-diphenylpent-3-en-1-yne derivatives paving the way for the preparation of tailored derivatives on mass scale necessary for biological studies and drug development. 相似文献
12.
Through the use of [PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst, a range of vinyl bromides undergoes Sonogashira cross-coupling reaction with a variety of alkynes, leading to the corresponding 1,3-enynes in good yields. The reaction tolerates several alkynes such as phenylacetylene, dec-1-yne, 2-methylbut-1-en-3-yne a range of alk-1-ynols, 3,3-diethoxyprop-1-yne and a propargyl amine. Higher reactions rates were observed in the presence of phenylacetylene, dec-1-yne, but-3-yn-1-ol, pent-4-yn-1-ol, 3,3-diethoxyprop-1-yne or 1,1-dipropyl-2-propynylamine than with propargyl alcohol, 3-methoxy-prop-1-yne or 2-methylbut-1-en-3-yne. This catalyst can be used at low loading even for reactions of sterically hindered vinyl bromides such as bromotriphenylethylene or 2-bromo-3-methyl-but-2-ene. 相似文献
13.
12-Deoxyscalarolactone and 12-deoxyscalaradial and substances related to them have been synthesized from methyl scalar-16-en-19-oate.Institute of Chemistry, Moldovan Academy of Sciences, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 499–503, September–October, 1992. 相似文献
14.
A. N. Nikol'skaya K. A. Volkova E. P. Levanova A. N. Volkov M. V. Sigalov 《Russian Chemical Bulletin》1975,24(12):2678-2680
Conclusions New unsaturated glycidyl ethers have been prepared by reaction of tert-1-alkoxy-1-en-3-ynols with epichlorohydrin in alkaline solution.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2792–2795, December, 1975. 相似文献
15.
V. N. Odinokov G. G. Balezina U. M. Dzhemilev G. Yu. Ishmuratov D. V. Amirkhanov V. P. Krivonogov F. Kh. Sitnikova G. A. Tolstikov 《Chemistry of Natural Compounds》1984,19(5):593-597
A highly stereospecific method for the synthesis of racemic (Z)-disparlure has been developed which is based on the reduction of 2-methyloctadec-7-yne with the aid of 9-borabicyclo[3.3.1]nonane and the epoxidation of the resulting (Z)-2-methyloctadec-7-ene with p-methoxycarbonylperbenzoic acid. The13C NMR spectra of the (Z) and (E) isomers of 2-methyloctadec-7-ene and 2-methyl-7,8-epoxyoctadecane, which unambiguously confirm the structures of these compounds, are given. It has been established that (E)-2-methyloctadec-7-ene exhibits a moderate attractant activity while the (Z) isomer does not attract the gypsy moth. The addition of 5–25% of (E)-disparlure increases the biological activity of (Z)-disparlure.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 630–634, September–October, 1983. 相似文献
16.
Conclusions 5-Methyl-3, 4-hexadien-1-yne was synthesized and some of its chemical transformations were studied.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1072–1075, May, 1973. 相似文献
17.
A simple synthesis of the nonadec-cis-7-en-11-one and eicos-cis-7-en-11-one, components of the sex pheromone of the peach moth, has been performed from homopropargyl alcohols.All-Union Scientific-Research Institute of Biological Methods of Plant Protection, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 123–126, January–February, 1988. 相似文献
18.
V. N. Odinokov O. S. Kukovinets V. G. Kasradze E. Yu. Tsyglintseva É. P. Serebryakov G. A. Tolstikov 《Chemistry of Natural Compounds》1992,28(1):106-109
A scheme has been developed for the synthesis of (R)-(–)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata) using as the chiral synthon (R)-(+)-methylheptenal obtained by the hydroperoxide oxidation of the readily available (S)-(+)-dihydromyrcene.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 125–129, January–February, 1992. 相似文献
19.
A method has been developed for obtaining (Z)tetradec-11-en-1-ol and (Z)-hexadec-11-en-1-ol via dodec-11-yn-1-ol.A. N. Nesmeyanov Institute of Organometallic Compounds, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 776–779, November–December, 1984. 相似文献
20.
Matar Seck Reynald Hocquemiller Jean-François Peyrat Jean-Daniel Brion 《Tetrahedron letters》2004,45(9):1881-1884
This letter reports the preparation of quinolines, substituted at the 2- or 3-position by a 4-substituted but-3-en-1-yne group, by the environmentally friendly iron(III)-catalyzed coupling reaction of Grignard reagents with 1-chloro-4-(2-quinolyl)but-1-en-3-yne. The extension and the scope of this non-toxic and chemoselective procedure to various functionalized unsaturated vinyl chlorides are described. 相似文献