- A Systematic Study on the Synthesis of n-Butyl Substituted 8-Aminoquinolines
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(Chemical Equation Presented) A systematic study on the synthesis of 8-aminoquinoline derivatives with an n-butyl group at each alternate position of the quinoline ring was carried out. Skraup Reaction and its Doebner-von Miller variation were used to obtain most of the quinoline ring except for the 2-butyl-8-aminoquinolines and 4-butyl-8-aminoquinolines where the commercially available methylquinoline derivatives were used as precursors. The structures of the synthesized compounds were characterized by FTIR, 1H-NMR, COSY, 13C-NMR and HRMS spectra.
- Koseoglu, Ahmet,Gul, Turan,Acar, Ali Ersin
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- Efficient synthesis of (±)-4-methyloctanoic acid, aggregation pheromone of rhinoceros beetles of the genus oryctes (Coleoptera: Dynastidae, Scarabaeidae)
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(±)-4-Methyloctanoic acid and its ethyl ester are aggregation pheromones of many rhinoceros beetles of the genus Oryctes and are investigated for the control of these pests by olfactory trapping. A simple, economical, and high-yield (>50%) synthesis of (±)-4-methyloctanoic acid and its ethyl ester is presented starting from n-hexanal. The key step in this sequence is an orthoester Claisen rearrangement for the elongation of the carbon chain by two.
- Ragoussis, Valentine,Giannikopoulos, Alexandros,Skoka, Efthymia,Grivas, Panagiotis
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- ODORANTS AND COMPOSITIONS COMPRISING ODORANTS
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The present invention relates to new classes of odorous 3-(2- methylenealkoxy)alkanenitrile derivatives of formula (I) which are useful as fragrance or flavor materials in particular in providing dry, woody, dusty, earthy, and/or patchouli notes together with optional coriander, aldehydic, citrus, mandarin, pear, cinnamon, and/ or petal floral-like notes to perfume, aroma or deodorizing/masking compositions.
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Page/Page column 29-30
(2021/10/22)
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- Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter
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A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.
- Dong, Kaiwu,Li, Huimin,Ren, Xinyi,Shen, Chaoren,Tang, Lin,Wang, Peng
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supporting information
p. 3561 - 3566
(2021/05/29)
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- COMPOSITIONS COMPRISING ODORANTS
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The present invention relates to odorous 2- and/or 3-substituted 3-(allyloxy)propenes which are useful as fragrance or flavor ingredients in particular in providing green, fruity, pear and/or waxy olfactory notes. The present invention also relates to novel perfume, aroma or deodorizing/masking compositions comprising said odorants.
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Page/Page column 21
(2019/02/25)
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- Exploration of Diverse Reactive Diad Geometries for Bifunctional Catalysis via Foldamer Backbone Variation
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What is the best spatial arrangement of a pair of reactive groups for bifunctional catalysis of a chemical transformation? The conformational versatility of proteins allows reactive group geometry to be explored and optimized via evolutionary selection, but it has been difficult for chemists to identify synthetic scaffolds that allow broad comparative evaluation among alternative reactive group geometries. Here we show that a family of helices, adopted predictably by oligomers composed partially or exclusively of β-amino acid residues, enables us to explore a range of orientations for a pair of pyrrolidine units that must work in tandem to catalyze a crossed aldol reaction. Thus, the crossed aldol reaction serves as an assay of reactive diad efficacy. We have chosen a test reaction free of stereochemical complexity in order to streamline our study of reactivity. The best geometry enhances the initial rate of product formation by two orders of magnitude. Our findings raise the possibility that rudimentary catalysts involving an isolated secondary structure might have facilitated the development of prebiotic reaction networks.
- Girvin, Zebediah C.,Gellman, Samuel H.
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supporting information
p. 12476 - 12483
(2018/09/27)
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- Structure-activity relationship study of a series of novel oxazolidinone derivatives as IL-6 signaling blockers
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A series of oxazolidinone and indole derivatives were synthesized and evaluated as IL-6 signaling blockers by measuring the effects of these compounds on IL-6-induced luciferase expression in human hepatocarcinoma HepG2 cells transfected with p-STAT3-Luc. Among different compounds screened, compound 4d was emerged as the most potent IL-6 signaling blockers with IC50 value of 5.9 μM which was much better than (+)-Madindoline A (IC50 = 21 μM), a known inhibitor of IL-6.
- Singh, Sarbjit,Gajulapati, Veeraswamy,Gajulapati, Kondaji,Goo, Ja-Il,Park, Yeon-Hwa,Jung, Hwa Young,Lee, Sung Yoon,Choi, Jung Ho,Kim, Young Kook,Lee, Kyeong,Heo, Tae-Hwe,Choi, Yongseok
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supporting information
p. 1282 - 1286
(2016/02/23)
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- Expanding the Scope of the Gold(I)-Catalyzed Rautenstrauch Rearrangement: Protic Additives
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The synthesis of substituted 2-cyclopentenones using a commercially available gold(I) catalyst is described under flexible reaction conditions. During the course of our investigations, we discovered that using a proton source as an additive is required to obtain the desired substituted cyclopentenones in good yields.
- Bürki, Cédric,Whyte, Andrew,Arndt, Sebastian,Hashmi, A. Stephen K.,Lautens, Mark
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supporting information
p. 5058 - 5061
(2016/10/14)
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- Synthesis of the C-18-C-34 fragment of amphidinolides C, C2, and C3
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The C-18-C-34 fragment of amphidinolides C, C2, and C3 and the C-18-C-29 fragment of amphidinolide F have been constructed from a trans-2,5-disubstituted dihydrofuran. This key intermediate was prepared from a dihydrofuranone formed by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The side chains found in amphidinolides C and F were introduced using Sonogashira coupling reactions.
- Clark, J. Stephen,Yang, Guang,Osnowski, Andrew P.
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p. 1464 - 1467
(2013/06/27)
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- Manganese(III) acetate mediated oxidative radical cyclizations. Toward vicinal all-carbon quaternary stereocenters
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Manganese(III) acetate mediated oxidative radical cyclizations have been used to synthesize a range of densely functionalized and sterically congested cyclopentane-lactones. A number of the resulting lactones contain vicinal all-carbon quaternary stereocenters adjacent to a tertiary benzylic stereocenter and are formed with high levels of stereocontrol.
- Logan, Angus W.J.,Parker, Jeremy S.,Hallside, Michal S.,Burton, Jonathan W.
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supporting information; experimental part
p. 2940 - 2943
(2012/08/28)
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- Organocatalyzed cyclopropanation of α-substituted α,β-unsaturated aldehydes: Enantioselective synthesis of cyclopropanes bearing a chiral quaternary center
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An enantioselective cyclopropanation of α-substituted α,β-unsaturated aldehydes with bromomalonate has been successfully developed through a domino Michael/a-alkylation strategy. The method allows the efficient formation of cyclopropanes bearing a quaternary carbon stereocenter at the a-position of the aldehydes by using iminium/enamine catalysis and gives a nice extension on the organocatalytic cyclopropanation of bromomalonate and α β-unsaturated aldehydes previously reported by other groups. Very good yields (up to 81%) and enantioselectivities (up to 97% ee) have been obtained. The optically active cyclopropane derivatives are of high synthetic interest as useful targets for further elaboration into more complex structures. 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim aldehydes, cyclopropanes, domino reactions, organocatalysis, quaternary stereocenters.
- Terrasson, Vincent,Van Der Lee, Arie,De Figueiredo, Renata Mareia,Campagne, Jean Marc
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supporting information; experimental part
p. 7875 - 7880
(2010/09/18)
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- Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration
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(Chemical Equation Presented) Asymmetric 1,4-dihydroxylations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B2(pin) 2) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyclic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereoselective carbonyl allylation with the intermediate bis(boronate) ester is also described.
- Burks, Heather E.,Kliman, Laura T.,Morken, James P.
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supporting information; scheme or table
p. 9134 - 9135
(2009/12/05)
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- Organoleptic Compounds
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The present invention is directed to the fragrance compounds and their intermediates and a method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount wherein the dotted line represents a possible single or double bond; wherein R is equal to a C3-C7 hydrocarbon moieties R1 and R2 together can be selected from the group consisting of oxygen and may form a closed ring structure represented by
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- Fluoride-Promoted Rearrangement of Organo Silicon Compounds: A New Synthesis of 2-(Arylmethyl)aldehydes from 1-Alkynes
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A new approach to 2-(arylmethyl)aldehydes 4 based upon a 1,2-anionotropic rearrangement of an aryl group is presented. The synthetic sequence begins with a silylformylation reaction of terminal acetylenes 5 with aryl and heteroaryl silanes 6, followed by treatment of the products (Z)-1 with TBAF. The optimization of the experimental conditions of the fluoride-promoted step is described, together with the synthetic potentialities of the process. A plausible mechanism of the rearrangement reaction is reported that suggests the addition of the fluoride ion to the arylsilicon moiety of β-silylalkenals (Z)-1 and the consequent migration of the aryl group to the adjacent carbon atom. Both aryl and heteroaryl substituents can rearrange without any loss of configuration. Bromofunctionalized substrates undergo an intramolecular reaction that affords exclusively carbacyclobenzyl aldehydes, further enhancing the high synthetic value of this method.
- Aronica, Laura Antonella,Raffa, Patrizio,Caporusso, Anna Maria,Salvadori, Piero
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p. 9292 - 9298
(2007/10/03)
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- Contrast media synthesized from polyaldehydes
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Microparticles comprising biodegradable polymers, characterized in that they are synthesized from polymerizable aldehydes, which optionally contain additives and/or crosslinkers capable of copolymerization, optionally surfactants or surfactant mixtures, gases and/or highly volatile liquids in free or bound form, coupling agents, optionally biomolecules or macromolecules bound by these coupling agents as well as optionally diagnostically or therapeutically effective components, are suitable as ultrasonic contrast media.
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- SYNTHESIS OF β- AND γ-HYDROXY SULFONES BY REGIOSELECTIVE OPENING OF β,γ-EPOXY SULFONES
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β,γ-Epoxy sulfones 1 derived from allylic sulfones react regioselectively with organomagnesium compounds in the presence or not of catalytic amounts of copper(I) bromide to afford β-hydroxy sulfones 2 or γ-tosylated allylic alcoholates 5 respectively.The Michael type addition of Grignard reagents to intermediates 5 in the presence of catalytic amount of copper(I) bromide yields γ-hydroxy sulfones 6.The PCC oxidation of β- and γ-hydroxy sulfones give β- and γ-oxo sulfones 10 and 11 respectively.In the case of γ-oxo-sulfones their treatment with DBU affords α-substituted, α, β- unsaturated carbonyl compounds.
- Najera, Carmen,Sansano, Jose Miguel
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p. 3993 - 4002
(2007/10/02)
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- ALKENYL COPPER REAGENTS-18; CARBOCUPRATION OF ACETYLENIC ACETALS AND KETALS; SYNTHESIS OF MANICONE, GERANIAL AND 2,4(E,Z)-DIENALS
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Lithium diorganocuprates add across the triple bond of substituted and non-substituted acetylenyl acetals and ketals to give dialkenylcuprates, which can be decomposed into alkoxyallenes or may be trapped with a variety of electrophiles, such as alkyl, alkenyl, alkynyl and aryl halides.They may also undergo conjugate addition to α-β unsaturated esters and ketons.The method is used for the synthesis of (+/-)-manicone, pure geranial and (E,Z)2,4-dienals.
- Alexakis, A.,Commercon, A,Coulentianos, C.,Normant, J.F.
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p. 715 - 732
(2007/10/02)
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- Therapeutically active 3-amino-1-halogenated phenyl-2-pyrazolines and their C4 and C5 analogs
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A method of meliorating the inflammation and/or the progressive joint deterioration characteristic of arthritic disease, preventing the onset of asthmatic symptoms and allergic diseases, treating pain or treating bacterial and fungal infections in mammals using 3-amino-1-halogenated phenyl-2-pyrazolines and their C4 and C5 analogs.
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