16695-34-4Relevant articles and documents
SYNTHESIS OF 3E-TETRADECENOL, 3E,9E-TETRADECADIENOL, AND THEIR ACETATES STARTING FROM ACETYLCYCLOPROPANE
Ivanova, N. M.,Cheskis, B. A.,Rubanova, E. V.,Yatsynin, V. G.,Moiseenkov, A. M.,Nefedov, O. M.
, p. 557 - 561 (1991)
Stereospecific synthesis of the linear E-olefins mentioned in the title was realized by a general scheme that was worked out earlier by the authors and which includes as key step homologization of the corresponding aliphatic pentakisnoraldehydes by means of trimethylsilyloxyvinylcyclopropane and ZnBr2-initiated rearrangement of the intermediate cyclopropylcarbinols under the influence of Me3SiBr.
Insect pheromones and their analogs. LVIII. Synthesis of hexadeca-7Z,11E-dien-1-yl acetate - A component of the sex pheromones of Pectinophora gossypiella and Sitotroga cerealella
Odinokov,Vakhidov,Shakhmaev,Zorin
, p. 186 - 188 (1998)
A new synthesis of hexadeca-7Z,11E-dien-1-yl acetate - a component of the sex pheromones of the pink bollworm (Pectinophora gossypiella) and the Angoumois grain moth (Sitotroga cerealella) - is proposed that is based on a thermal Claisen rearrangement. Scientific-Research Institute of Small-Tonnage Chemical Products and Reagents, Ufa, fax 8-(3472) 43 17 31.
Stereoselective synthesis of alkenyl alcohols using dissolving metal(Ca,Na) reduction
Zhou,Lu,Huang,Wu
, p. 435 - 441 (1991)
Use of the calcium-ethylenediamine and sodium-liquid ammonia reduction systems for the ring opening of dihydropyran derivatives was studied. (Z)-Alkenyl alcohols and (E)-alkenyl alcohols were stereoselectively synthesized respectively.
STEREOSELECTIVE AND VERSATILE APPROACH FOR THE SYNTHESIS OF GOSSYPLURE AND ITS COMPONENTS
Joshi, N. N.,Mamdapur, V. R.,Chadha, M. S.
, p. 3285 - 3290 (1984)
Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated.The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials.Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the disired pheromone (1a + 1b).The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3.A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.
Access to Saturated Thiocyano-Containing Azaheterocycles via Selenide-Catalyzed Regio-A nd Stereoselective Thiocyanoaminocyclization of Alkenes
Wei, Wei,Liao, Lihao,Qin, Tian,Zhao, Xiaodan
, p. 7846 - 7850 (2019/10/10)
An efficient route for the synthesis of saturated thiocyano-containing azaheterocycles by selenide-catalyzed regio-A nd stereoselective thiocyanoaminocyclization of alkenes is disclosed. The desired products were obtained in moderate to high yields under mild conditions. The generality of this method was elucidated by its efficient application in thiocyano oxycyclization of alkenes.
Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates
Hazelden, Ian R.,Carmona, Rafaela C.,Langer, Thomas,Pringle, Paul G.,Bower, John F.
supporting information, p. 5124 - 5128 (2018/03/26)
Ligand-enabled aza-Heck cyclizations and cascades of N-(pentafluorobenzoyloxy)carbamates are described. These studies encompass the first examples of efficient non-biased 6-exo aza-Heck cyclizations. The methodology provides direct and flexible access to carbamate protected pyrrolidines and piperidines.
A facile access to bridged 1,2,4-trioxanes
Zhang, Qi,Jin, Hong-Xia,Wu, Yikang
, p. 11627 - 11634 (2007/10/03)
Bicyclo[3.2.1] type 1,2,4-trioxanes are readily synthesized from precursors that may form intramolecular hemiketals using UHP (H2O2-urea complex) as the source of the peroxy bond and p-TsOH or CSA as the catalyst. The ring closure through an intramolecular Michael addition occurred in a highly stereoselective way, giving only one diasteromer as shown by the NMR spectra.
1,2-Silyl-migrative cyclization of vinylsilanes bearing a hydroxy group: Stereoselective synthesis of multisubstituted tetrahydropyrans and tetrahydrofurans
Miura, Katsukiyo,Hondo, Takeshi,Okajima, Shigeo,Nakagawa, Takahiro,Takahashi, Tatsuyuki,Hosomi, Akira
, p. 6082 - 6090 (2007/10/03)
Acid-catalyzed intramolecular addition of a hydroxy group to α-alkylated vinylsilanes has been studied. Treatment of (Z)-5-alkyl-5-silyl-4-penten-1-ols 1 (R = alkyl) with 5 mol % TiCl4 in CHCl3 gave trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis = > 99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the C-C double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis-selectivity. In the cyclization of (Z)-1 (R = Bu), the silyl group used, the reaction time, and the yield of 2 were as follows: SiMe2Ph, 9.5 h, 75%; SiMe3, 7.5 h, 66%; SiMePh2, 24 h, 58%; SiMe2-t-Bu, 0.75 h, 85%; SiMe2Bn, 1.5 h, 78%. This 1,2-silyl-migrative cyclization could be applied to stereoselective synthesis of trisubstituted tetrahydropyrans. The acid-catalyzed reaction of 1-, 2-, or 3-substituted (Z)-5-silyl-4-nonen-1-ols 8 gave r-2,t-3,c-6-, r-2,t-3,t-5-, or r-2,t-3,c-4-trisubstituted tetrahydropyrans with high diastereo-selectivity, respectively. (Z)-4-Alkyl-4-silyl-3-buten-1-ols 5 as well as 1 underwent the 1,2-silylmigrative cyclization to give 2-alkyl-3-silyltetrahydrofurans 6 with high trans-selectivity. This silicon-directed cyclization was also available for the stereoselective synthesis of tri- and tetrasubstituted tetrahydrofurans.
Synergistic sex pheromone components of white-spotted tussock moth, Orgyia thyellina
Gries, Gerhard,Clearwater, John,Gries, Regine,Khaskin, Grigori,King, Skip,Schaefer, Paul
, p. 1091 - 1104 (2007/10/03)
In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic-electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6-11-one) and (Z)-6-heneicosen-9- one, the latter termed here 'thyellinone.' In field experiments in Japan, Z6- 11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997-1998 summer, 45,000 commercial trap lures baited with 2000 μg of Z6-11-one and 100 μg of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.
Preparation of Geometrical Isomers of 2,7-Dodecadienal, 2,7-Dodecadienyl Formate, and Other 1,6-Diene System-containing Compounds and Their Electroantennography Activities toward Male Eri-Silk Moths
Hatanaka, Akihiko,Ishii, Yasushige,Tomida, Ichiro
, p. 2036 - 2038 (2007/10/02)
We measured the electroantennography (EAG) activities of the geometrical isomers of several pheromone-related compounds towards male eri-silk moths (Samia cynthia richini) using EAG-gas chromatography (GC).C16-aldehyde and formyl ester, with the same chain length as C16-aldehyde, were found to be much more active than other compounds with a shorter chain.For the compounds with (1Z,6Z)- or (1E,6E)-configuration, the activity in decreasing order was C14-formyl ester > C16-aldehyde > C14-aldehyde > C12-formyl ester, while that for the compounds with (1Z,6E)- or (1E,6Z)-configuration is C16-aldehyde > C14-formyl ester > other compounds with a shorter C14 chain.
