15542-26-4Relevant academic research and scientific papers
Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis
Maeta, Naoya,Kamiya, Hidehiro,Okada, Yohei
supporting information, p. 6551 - 6566 (2020/07/14)
Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.
Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones
Koszelewski, Dominik,Paprocki, Daniel,Brodzka, Anna,Ostaszewski, Ryszard
, p. 809 - 818 (2017/06/13)
A novel synthetic route to optically active saturated and unsaturated δ-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate s
Lewis Base Activation of Silyl Acetals: Iridium-Catalyzed Reductive Horner-Wadsworth-Emmons Olefination
Dakarapu, Udaya Sree,Bokka, Apparao,Asgari, Parham,Trog, Gabriela,Hua, Yuanda,Nguyen, Hiep H.,Rahman, Nawal,Jeon, Junha
, p. 5792 - 5795 (2015/12/11)
A Lewis base promoted deprotonative pronucleophile addition to silyl acetals has been developed and applied to the iridium-catalyzed reductive Horner-Wadsworth-Emmons (HWE) olefination of esters and the chemoselective reduction of the resulting enoates. Lewis base activation of silyl acetals generates putative pentacoordinate silicate acetals, which fragment into aldehydes, silanes, and alkoxides in situ. Subsequent deprotonative metalation of phosphonate esters followed by HWE with aldehydes furnishes enoates. This operationally convenient, mechanistically unique protocol converts the traditionally challenging aryl, alkenyl, and alkynyl esters to homologated enoates at room temperature within a single vessel.
Facile Preparation of α-Cyano-α,ω-Diaryloligovinylenes: A New Class of Color-Tunable Solid Emitters
An, Peng,Xu, Nian-Sheng,Zhang, Hao-Li,Cao, Xiao-Ping,Shi, Zi-Fa,Wen, Wei
, p. 1959 - 1966 (2015/09/07)
An efficient Knoevenagel condensation reaction was used to construct a series of α-cyano-α,ω-diaryloligovinylenes, which show prominent fluorescence emission in the solid state. On investigating the effect of conjugation length on fluorescent properties,
A convenient conversion of terminal alkenes into homologous unsaturated and doubly unsaturated esters
Hawkins, Bill,Paddock, Victoria L.,Toelle, Nina,Zard, Samir Z.
supporting information; experimental part, p. 1020 - 1023 (2012/04/05)
Unsaturated and doubly unsaturated esters have been synthesized in two steps by the application of a radical xanthate transfer process of a simple methylsulfoxide starting material to a range of terminal alkenes. syn-Elimination of the sulfoxide gives α,β
Ruthenium/halide catalytic system for C-C bond forming reaction between alkynes and unsaturated carbonyl compounds
Nishimura, Takahiro,Washitake, Yosuke,Uemura, Sakae
, p. 2563 - 2571 (2008/09/19)
A ruthenium complex [triruthenium dodecacarbonyl, Ru3(CO) 12] in the presence of bis(triphenylphosphine)iminium chloride ([PPN]Cl) catalyzes the conjugate addition of terminal alkynes to alkyl acrylates to give high yields of γ,δ-alkynyl esters. On the other hand, the linear codimerization reaction of terminal alkynes with alkyl acrylates proceeds in the presence of a catalytic amount of Ru 3(CO)12 and lithium iodide to give the corresponding conjugate dienes. These two different types of catalytic carbon-carbon bond forming reactions are controlled only by the nature of halide ions, either a chloride or an iodide, with other conditions being kept almost the same.
BENZOTHIAZIN-3-ONE COMPOUND AND INTERMEDIATE THEREFOR
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Page/Page column 41-42, (2008/06/13)
A medicine which contains as an active ingredient a benzothiazin-3-one-compound represented by the formula (1): (wherein n is 3 or 4; R represents ethyl or hydrogen; and R 1 represents hologeno, alkoxy, haloalkyl, or haloalkoxy) or a pharmaceutically acceptable salt thereof. It is useful as a therapeutic or preventive agent for arthrosis deformans, chondrodegenerative discases such as chronic articular rheumatism, cancers, gingivitis, etc. Also provided are an intermediate for the compound and a process for producing the compound.
Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities
Koul, Surrinder,Koul, Jawahir L.,Taneja, Subhash C.,Dhar, Kanaya L.,Jamwal, Deshvir S.,Singh, Kuldeep,Reen, Rashmeet K.,Singh, Jaswant
, p. 251 - 268 (2007/10/03)
Inhibitors of drug metabolism have important implications in pharmaco- toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)-dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd.
Telluro-directed regiospecific and highly stereoselective reaction of ethyl 5-telluro-(2E,4Z)-pentadienoate with organocopper reagents
Huang, Yao-Zeng,Mo, Xue-Sheng,Wang, Lei
, p. 419 - 422 (2007/10/03)
Ethyl 5-telluro-(2E,4Z)-pentadienoate 2, which is prepared by the Wittig olefination of (Z)-β-telluroacrolein 1, reacted very rapidly with organocuprates 3 at -78°C to form exclusively the corresponding 5-substituted products 4 with high stereoselectivity
Novel Synthesis of Phenol Derivatives by Palladium-Catalyzed Cyclocarbonylation of 2,4-Pentadienyl Acetates
Ishii, Youichi,Gao, Chao,Xu, Wen-Xiang,Iwasaki, Masakazu,Hidai, Masanobu
, p. 6818 - 6825 (2007/10/02)
Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140 deg C under 50 atm of CO.No five-membered ring products were observed.A platinum complex PtCl2(PPh3)2 was also effective as a catalyst.The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3,5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51percent yield on heating to 160 deg C under 50 atm of CO in the presence of NEt3 and Ac2O.Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates.On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO, respectively.
