74962-98-4Relevant articles and documents
Stereoretentive Olefin Metathesis Made Easy: In Situ Generation of Highly Selective Ruthenium Catalysts from Commercial Starting Materials
Müller, Daniel S.,Curbet, Idriss,Raoul, Yann,Le N?tre, Jér?me,Baslé, Olivier,Mauduit, Marc
supporting information, p. 6822 - 6826 (2018/10/31)
The in situ preparation of highly stereoretentive ruthenium-based metathesis catalysts is reported. This approach completely avoids the isolation of intermediates and air-sensitive catalysts, thus allowing for the rapid access and evaluation of numerous dithiolate Ru catalysts. A procedure was established to perform cross-metathesis reactions without the use of a glovebox, and on a small scale even Schlenk techniques are not required. Consequently, the chemistry displayed in this report is available to every practicing organic chemist and presents a powerful approach for the identification of new stereoretentive catalysts.
Structure-Activity relationship of aliphatic compounds for nematicidal activity against pine wood nematode (Bursaphelenchus xylophilus)
Seo, Seon-M.I.,Junheon, Kim,Eunae, Kim,Park, Hye-M.I.,Kim, Young-Joon,Park, I.L.-Kwon
experimental part, p. 1823 - 1827 (2010/09/09)
Nematicidal activity of aliphatic compounds was tested to determine a structure-activity relationship. There was a significant difference in nematicidal activity among functional groups. In a test with alkanols and 2E-alkenols, compounds with C8-C11 chain length showed 100% nematicidal activity against pine wood nematode, Bursaphelenchus xylophilus, at 0.5 mg/mL concentration. C6-C10 2E-alkenals exhibited >95% nematicidal activity, but the other compounds with C 11-C14 chain length showed weak activity. Nematicidal activity of alkyl acetates with C7-C11 chain length was strong. Compounds belonging to hydrocarbons, alkanals, and alkanoic acetates showed weak activity at 0.5 mg/mL concentration. Nematicidal activity of active compounds was determined at lower concentrations. At 0.25 mg/mL concentration, whole compounds except C8 alkanol, C8 2E-alkenol, and C7 alkanoic acid showed >80% nematicidal activity. C 9-C11 alkanols, C10-C11 2E-alkenols, C8-C9 2E-alkenals, and C9-C10 alkanoic acids showed >80% nematicidal activity at 0.125 mg/mL concentration. Only C11 alkanol exhibited strong nematicidal activity at 0.0625 mg/mL concentration, the lowest concentration that was tested. 2010 American Chemical Society.
Synthesis of disparlure analogues, using resolution on microcrystalline cellulose triacetate-I
Inkster, James A. H.,Ling, Ivy,Honson, Nicolette S.,Jacquet, Loic,Gries, Regine,Plettner, Erika
, p. 3773 - 3784 (2007/10/03)
The gypsy moth, Lymantria dispar, uses a chiral epoxide, (+)-(7R,8S)-2-methyl-7,8-epoxyoctadecane, (+)-disparlure, as its main sex attractant. The moths can detect both enantiomers of disparlure and respond differently to each one. In an effort to understand the structure-activity relationships of the gypsy moth olfactory system, we prepared the analogues of (+)- and (-)-disparlure. The key intermediate in route to the analogues was 2-epoxytridecan-1-ol. Herein we report the resolution of 2-epoxytridecan-1-yl esters on microcrystalline cellulose triacetate and the synthesis of 5-oxa and (5Z)-ene analogues of (+)- and (-)-disparlure. An effort to make 5-aza analogues resulted in the formation of anti-5-(1-hydroxy-1-undecyl)-3-(3-methylbutyl) oxazolidin-2-one. The analogues were tested for their electroantennogram responses and for their ability to bind to pheromone-binding protein 1 (PBP1). We found that the 5-oxa analogues gave strong responses and that the antenna and the PBP1 no longer distinguish the enantiomers of the 5-oxa analogues. The analogues all bound the PBP1 with similar affinity to (-)-disparlure.
