13594-95-1Relevant academic research and scientific papers
Discovery of a novel series of peroxisome proliferator-activated receptor α/γ dual agonists for the treatment of type 2 diabetes and dyslipidemia
Liu, Kun,Xu, Libo,Berger, Joel P.,MacNaul, Karen L.,Zhou, Gauchao,Doebber, Thomas W.,Forrest, Michael J.,Moller, David E.,Jones, A. Brian
, p. 2262 - 2265 (2005)
A series of 2-aryloxy-2-methyl-propionic acid compounds and related analogues were designed, synthesized, and evaluated for their PPAR agonist activities. 2-[(5,7-Dipropyl-3-trifluoromethyl)-benzisoxazol-6-yloxy]-2- methylpropionic acid (4) was identified
Novel synthesis of medium-sized oxa-heterocycles by palladium-catalyzed intramolecular Heck reaction
Majumdar,Chattopadhyay,Ray
, p. 7633 - 7636 (2007)
An efficient and high yielding method for the synthesis of eight-membered heterocyclic skeletons has been developed via palladium-catalyzed intramolecular Heck reaction.
An expedient synthesis of bis-fused benzofuran and a two-directional ring- closing metathesis for the synthesis of bisbenzoxepines and bisbenzoxocines
Majumdar, Krishna C.,Chattopadhyay, Buddhadeb,Chakravorty, Santanu
, p. 674 - 680 (2009)
Synthesis of bis-fused benzofuran derivatives by the implementation of palladium-mediated intramolecular cyclization is described. To our knowledge, this is the first report of the synthesis of bis-fused benzofuran by this protocol. Bisbenzoxepine and bis
An easy and efficient access to bis-allyloxy-arenes
Kolodziuk,Kryczka,Lhoste,Porwanski,Sinou,Zawisza
, p. 3955 - 3961 (2000)
Bis-allyloxy-arenes were prepared in very good yields by reaction of the bis-hydroxy-arene on the appropriate allyl carbonate at room temperature in the presence of a palladium(0) catalyst.
Preparation of 1,3-bis(allyloxy)benzene under a new multi-site phase-transfer catalyst combined with ultrasonication - A kinetic study
Selvaraj, Varathan,Rajendran, Venugopal
, p. 1236 - 1244 (2013)
In the present work, kinetics of synthesis of 1,3-bis(allyloxy)benzene was successfully carried out by O-allylation of resorcinol with allyl bromide using aqueous potassium hydroxide and catalyzed by a new multi-site phase-transfer catalyst viz., 1,3,5,7-tetrabenzylhexamethylenetetraammonium tetrachloride, MPTC under ultrasonic (40 kHz, 300 W) assisted organic solvent condition. The pseudo first-order kinetic equation was applied to describe the overall reaction. Under ultrasound irradiation (40 kHz, 300 W) in a batch reactor, it shows that the overall reaction rate can be greatly enhanced to seven fold faster with ultrasound irradiation than without ultrasound. The present study provides a method to synthesize ethers by ultrasound assisted liquid-liquid phase-transfer catalysis condition.
Design and discovery of 2-oxochromene derivatives as liver X receptor β-selective agonists
Matsuda, Takayuki,Okuda, Ayumu,Watanabe, Yuichiro,Miura, Tohru,Ozawa, Hidefumi,Tosaka, Ayako,Yamazaki, Koichi,Yamaguchi, Yuki,Kurobuchi, Sayaka,Koura, Minoru,Shibuya, Kimiyuki
supporting information, p. 1274 - 1278 (2015/03/14)
In an attempt to molecularly design liver X receptor (LXR) β-selective agonists, we discovered that the combination of the 2-oxochromene moiety (head) and the imidazoline-2,4-dione moiety (tail) plays an important role in the expression potency and select
Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, trichoplusia ni: Potential insect behavior control agents
Akhtar, Yasmin,Yu, Yang,Isman, Murray B.,Plettner, Erika
scheme or table, p. 4983 - 4991 (2011/08/06)
The antifeedant, oviposition deterrent, and toxic effects of individual dialkoxybenzene compounds/sets and of hydroxy- or alkoxy-substituted allylbenzenes, obtained through Claisen rearrangement of substituted allyloxybenzenes, were assessed against the cabbage looper, Trichoplusia ni, in laboratory bioassays. Most of the compounds/sets strongly deterred larval feeding, with some exhibiting mild toxic and oviposition deterrent effects as well. Some of the compounds/sets were more active than the commercial insect repellent, DEET (N,N-diethyl-m-toluamide), as both feeding and oviposition deterrents against the cabbage looper. On the basis of the obtained oviposition data a general hypothesis was proposed regarding the oviposition sites: one binding mode with the alkyl and allyl groups on the same side of the benzene ring resulted in deterrence, the other with alkyl and allyl groups on opposite sides of the benzene ring resulted in stimulation. The results suggest some structure-activity relationships useful in improving the efficacy of the compounds and designing new, nontoxic insect control agents for agriculture.
METHODS AND COMPOSITIONS FOR CONTROL OF GYPSY MOTHS, Lymanria dispar
-
Page/Page column 11, (2010/08/07)
The invention provides in part dialkoxybenzene and eugenol compounds for controlling infestation by a Lymantria dispar, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; with the provisos that when R2 is at position 2, R3 if present is at position 3, or when R2 is at to position 3, R3 if present is at positions 2 or 4, or when R2 is at position 4, R3 if present is at position 2; or of Formula II: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; or mixtures thereof.
METHODS AND COMPOSITIONS FOR CONTROL OF CABBAGE LOOPER, Trichoplusia ni
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Page/Page column 11, (2010/07/04)
The invention provides in part dialkoxybenzene compounds for controlling infestation by a Trichoplusia ni, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; except that when R2 is at position 2, R3 if present is at position 3, and when R2 is at position 3, R3 if present is at positions 2 or 4, and when R2 is at position 4, R3 if present is at position 2, and when R2 is at position 4 and R3, if present, has reacted with an OH group at position 1 in a Markovnikov sense, then R3 becomes R4, a dihydrofuran.
Effect of ortho-SR groups on O-H bond strength and H-atom donating ability of phenols: A possible role for the tyr-cys link in galactose oxidase active site?
Amorati, Riccardo,Catarzi, Francesca,Menichetti, Stefano,Pedulli, Gian Franco,Viglianisi, Caterina
, p. 237 - 244 (2008/09/21)
Rotation about the Ar-S bond in ortho-(alkylthio)phenols strongly affects the bond dissociation enthalpy (BDE) and the reactivity of the OH group. Newly synthesized sulfur containing heterocycles 3 and 4, where the -SR group is almost coplanar with the phenolic ring, are characterized by unusually low BDE(O-H) values (79.6 and 79.2 kcal/mol, respectively) and by much higher reactivities toward peroxyl radicals than the ortho-methylthio derivative 1 (82.0 kcal/mol). The importance of the intramolecular hydrogen bond (IHB) in determining the BDE(O-H) was demonstrated by FT-IR experiments, which showed that in heterocycles 3 and 4 the IHB between the phenolic OH group and the S atom is much weaker than that present in 1. Since the IHB can be formed only if the -SR group adopts an out-of-plane geometry, this interaction is possible only in the methylthio derivative 1 and not in 3 and 4. The additive contribution to the phenolic BDE(O-H) of the -SR substituent therefore varies from -3.1 to +2.8 kcal/mol for the in-plane and out-of-plane conformations, respectively. These results may be relevant to understanding the role of the tyrosine-cysteine link in the active site of galactose oxidase, an important enzyme that catalyzes the two-electron aerobic oxidation of primary alcohols to aldehydes. The switching of the ortho -SR substituent between perpendicular and planar conformations may account for the catalytic efficiency of this enzyme.
