67446-07-5Relevant articles and documents
Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**
Browne, Duncan L.,Colombel-Rouen, Sophie,Crévisy, Christophe,Curbet, Idriss,Mauduit, Marc,McBride, Tom,Morvan, Jennifer,Roisnel, Thierry
supporting information, p. 19685 - 19690 (2021/08/06)
The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.
Stereoselective Chromium-Catalyzed Semi-Hydrogenation of Alkynes
Gregori, Bernhard J.,Nowakowski, Michal,Schoch, Anke,P?llath, Simon,Zweck, Josef,Bauer, Matthias,Jacobi von Wangelin, Axel
, p. 5359 - 5363 (2020/09/03)
Chromium complexes have found very little applications as hydrogenation catalysts. Here, we report a Cr-catalyzed semi-hydrogenation of internal alkynes to the corresponding Z-alkenes with good stereocontrol (up to 99/1 for dialkyl alkynes). The catalyst comprises the commercial reagents chromium(III) acetylacetonate, Cr(acac)3, and diisobutylaluminium hydride, DIBAL?H, in THF. The semi-hydrogenation operates at mild conditions (1-5 bar H2, 30 °C).
Stereoselective Alkyne Hydrogenation by using a Simple Iron Catalyst
Gregori, Bernhard J.,Schwarzhuber, Felix,P?llath, Simon,Zweck, Josef,Fritsch, Lorena,Schoch, Roland,Bauer, Matthias,Jacobi von Wangelin, Axel
, p. 3864 - 3870 (2019/07/31)
The stereoselective hydrogenation of alkynes constitutes one of the key approaches for the construction of stereodefined alkenes. The majority of conventional methods utilize noble and toxic metal catalysts. This study concerns a simple catalyst comprised of the commercial chemicals iron(II) acetylacetonate and diisobutylaluminum hydride, which enables the Z-selective semihydrogenation of alkynes under near ambient conditions (1–3 bar H2, 30 °C, 5 mol % [Fe]). Neither an elaborate catalyst preparation nor addition of ligands is required. Mechanistic studies (kinetic poisoning, X-ray absorption spectroscopy, TEM) strongly indicate the operation of small iron clusters and particle catalysts.
Synthesis of heneicos-6(Z)-en-11-one, dec-5(Z)-en-l-yl acetate, dec-5(Z)-En-1-y1-3-methylbutanoate (insect sex pheromones)
Jindal, Rani,Devi, Aarti,Kad, Goverdhan L.,Singh, Jasvinder
experimental part, p. 495 - 499 (2010/10/20)
Synthesis of heneicos-6(Z)-en-11-one 1, dec-5(Z)-en-l-yl acetate 2, dec-5(Z)-en-l-yl-3-methylbutanoate 3 has been accomplished by utilizing sodium acetoxyborohydride generated in situ from sodium borohydride and acetic acid as the key step for selective hydroboration-iodination/oxidation.
Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates
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Page/Page column 5, (2010/05/13)
Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.
Preparative synthesis of (Z)-5-decenyl acetate
Chobanyan
, p. 2036 - 2037 (2007/10/03)
A procedure was developed for preparative synthesis of (Z)-5-decenyl acetate, the sex hormone of Agrotis Segetum.
Synthesis of (Z)-5-decenol and (Z)-5-decenyl acetate, components of the sex pheromones of a variety of lepidoptera
Tortajada, Amparo,Mestres, Ramon,Iglesias-Arteaga, Martin A.
, p. 1809 - 1814 (2007/10/03)
Two simple Wittig procedures for the synthesis of (Z)-5-decenol and (Z)-5-decenyl acetate based on the monoacetylation or monobromination of 1,5-pentanediol were followed.
New synthesis of (Z)-5- and (Z)-7-monoene components of insect sex pheromones of the Lepidoptera order
Bykov,Butenko,Egupova,Finkelshtein
, p. 1301 - 1304 (2007/10/03)
A new procedure was developed for the synthesis of (Z)-5- and (Z)-7-monoene components of sex pheromones of Lepidoptera insects based on cometathesis of readily accessible cycloocta-1,5-diene and ethylene.
Synthesis of sub-units of marine polycyclic ethers by ring-closing metathesis and hydroboration of enol ethers
Bykov, Victor I.,Butenko, Tamara A.,Petrova, Elena B.,Finkelshtein, Eugene Sh.
, p. 8249 - 8252 (2007/10/03)
A novel syntheses of Z-5-dezenol, Z-5-decenyl acetate, Z-7-dodecenol, Z- 7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCls/SiO2-SnMe4 as a key reaction. The male cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components monocloned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp2ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-C2-homologation of the latter but to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9- tricosene, the main sex pheromone component of House Fly (Musca Domestica), or in 2-methyl-Z-7-octadecene, the presence of Gypsy Moth (Lymantria Dispar) sex attractant.
