13249-60-0Relevant articles and documents
Structure-Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in Bombyx mori
Ando, Tetsu,Ohno, Ryuta,Ikemoto, Kazuhisa,Yamamoto, Masanobu
, p. 3350 - 3354 (1996)
According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C16 chain and the 11,12-position in a C14 or C18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E, 12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 μg/gland, but other compounds at 1 μg/gland inhibited the conversion of [16,16,16-2H3]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C16 chain was the strongest (I50 = 0.016 μg/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-14C]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the Δ11-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Δ10,-12-desaturation by 11,12- and 13,14-methylene compounds.
Br?nsted Acid-Catalyzed Enantioselective Iodocycloetherification Enabled by Triphenylphosphine Selenide Cocatalysis
Daniliuc, Constantin G.,Guria, Sudip,Hennecke, Ulrich
, p. 3852 - 3858 (2021)
Enantioselective iodocycloetherifications can be conducted using sterically highly demanding BINOL-based phosphoric acid diesters as catalyst. To achieve highly enantioselective reactions, cocatalysis by triphenylphosphine selenide is necessary. With coca
Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides
Imazaki, Yusuke,Shirakawa, Eiji,Ueno, Ryota,Hayashi, Tamio
supporting information, p. 14760 - 14763 (2012/11/07)
Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)3]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η'1- arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.
α-Selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: Practical syntheses of internal vinyl aluminums, halides, or boronates
Gao, Fang,Hoveyda, Amir H.
supporting information; experimental part, p. 10961 - 10963 (2010/09/17)
A method for Ni-catalyzed hydroalumination of terminal alkynes, leading to the formation of α-vinylaluminum isomers efficiently (>98% conv in 2-12 h) and with high selectivity (95% to >98% α), is described. Catalytic α-selective hydroalumination reactions proceed in the presence of a reagent (diisobutylaluminum hydride; dibal-H) and 3.0 mol % metal complex (Ni(dppp)Cl2) that are commercially available and inexpensive. Under the same conditions, but with Ni(PPh3)2Cl2, hydroalumination becomes highly β-selective, and, unlike uncatalyzed transformations with dibal-H, generates little or no alkynylaluminum byproducts. All hydrometalation reactions are reliable, operationally simple, and practical and afford an assortment of vinylaluminums that are otherwise not easily accessible. The derived α-vinyl halides and boronates can be synthesized through direct treatment with the appropriate electrophiles [e.g., Br 2 and methoxy(pinacolato)boron, respectively]. Ni-catalyzed hydroaluminations can be performed with as little as 0.1 mol % catalyst and on gram scale with equally high efficiency and selectivity.
