cas 1871-67-6, TRANS-2-OCTENOIC ACID | Articles data

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Reaction of a lysyl residue analogue with E-2-octenal
The reaction of E-2-octenal and N2-(carbobenzyloxy)-L-lysine was investigated and the products analyzed to identify the components that produce a significant loss of lysine residues in the reaction of E-2-octenal and proteins. When the mixture of N2-(carbobenzyloxy)-L-lysine and E-2-octenal was incubated at pH 7.0 and 37 deg C for 24 h, seven products were isolated, and their structures are suggested to be E-2-octenoic acid (4), 4-butyl-E-2-E-4-E-6-dodecatrien-1-al (3), 6-ethyl-5-pentyl-1,3-cyclohexadiene (1), 3,8-dibutyl-1-(2'-butyl-4'-formyl-1'-E-3'-E-butadien-1'-yl) -5-pentyl-2,6-dihydronaftalene (2), 1-(N2-(carbobenzyloxy)-L-lysyl)-2-(1'-carboxymethyl)-4-pentylpyridinium betaine (6), 1-(N2-(carbobenzyloxy)-L-lysyl)-2-(3'-carboxy-2'-E-propen-1'-yl)-4-pentylpyridinium betaine (7) and bis(1-(N2-(carbobenzyloxy)-L-lysyl)-2-(3'-carboxy-2'-propen-1',2'-diyl)-4-pentylpyridinium betaine) (5). Plausible mechanisms for the formation of those compounds are proposed. Keywords: N2-(Carbobenzyloxy)-L-lysine; E-2-Octenal; Pyridinium salts; Reaction
Alaiz, Manuel,Barragan, Santiago
p. 43 - 50
(1995)
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Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C–H activation
Dehydrogenative transformations of alkyl chains to alkenes through methylene carbon-hydrogen (C–H) activation remain a substantial challenge. We report two classes of pyridine-pyridone ligands that enable divergent dehydrogenation reactions through palladium-catalyzed b-methylene C–H activation of carboxylic acids, leading to the direct syntheses of a,b-unsaturated carboxylic acids or g-alkylidene butenolides. The directed nature of this pair of reactions allows chemoselective dehydrogenation of carboxylic acids in the presence of other enolizable functionalities such as ketones, providing chemoselectivity that is not possible by means of existing carbonyl desaturation protocols. Product inhibition is overcome through ligand-promoted preferential activation of C(sp3)–H bonds rather than C(sp2)–H bonds or a sequence of dehydrogenation and vinyl C–H alkynylation. The dehydrogenation reaction is compatible with molecular oxygen as the terminal oxidant.
Wang, Zhen,Hu, Liang,Chekshin, Nikita,Zhuang, Zhe,Qian, Shaoqun,Qiao, Jennifer X.,Yu, Jin-Quan
p. 1281 - 1285
(2021/12/10)

Method for preparing alpha, beta-unsaturated carboxylic acid by reacting alkenyl boron compound with carbon dioxide under catalysis of cuprous halide
The invention discloses a method for preparing alpha, beta-unsaturated carboxylic acid through a carboxylation reaction of an alkenyl boron compound and carbon dioxide under the catalysis of cuprous halide. According to the method, carbon dioxide is used as a C1 source, the cuprous halide is adopted for catalysis, and alkoxide serves as alkali to react in an organic solvent, so the method is simple and easy to implement, has a wide substrate application range, converts various alkenyl boron compounds such as alkenyl boric acid, alkenyl borate and borate into corresponding alpha, beta-unsaturated carboxylic acid under mild conditions, and has a very high yield. The obtained product alpha, beta-unsaturated carboxylic acid is an important intermediate for preparing fine chemical products suchas perfumes, insecticides and the like.
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Paragraph 0061-0062

(2020/06/17)

Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO2 Catalyzed by Cuprous Halide
A cuprous halide catalysed carboxylation of alkenyl boronic acids and alkenyl boronic acid pinacol esters under CO2, affording the corresponding α, β-unsaturated carboxylic acids in good yield, has been developed. The potassium (E)-trifluoro(styryl)borate is also compatible with this reaction. This simple and efficient copper(I) catalytic system showed good functional group tolerance.
Hong, Junting,Nayal, Onkar S.,Mo, Fanyang
supporting information
p. 2813 - 2818
(2020/05/16)

Preparation method of (E, Z)-2, 4-ethyl decadienoate
The invention provides a preparation method of (E, Z)-2, 4-ethyl decadienoate. According to the preparation method, n-hexyl aldehyde is taken as an initial raw material, and three step chemical conversion is adopted to prepare a key intermediate 1-bromo heptene; 1-bromo heptene and ethyl acrylate are subjected to coupling reaction under the catalytic effect of a metal catalyst so as to obtain (E,Z)-2, 4-ethyl decadienoate. According to the preparation method, metal catalytic coupling reaction is adopted to replace a step in the prior art that (E, Z)-2, 4-ethyl decadienoate is prepared throughpreparation of an organic copper lithium reagent, water-free oxygen-free harsh conditions are avoided, operation is simplified, reaction efficiency is increased, generation of waste water and waste salt is reduced greatly, equipment investment is reduced, and the preparation method is convenient for industrialization production.
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Paragraph 0040; 0041

(2019/05/15)

Unexpected AChE inhibitory activity of (2E)α,β-unsaturated fatty acids
A small library of (E) α,β-unsaturated fatty acids was prepared, and 20 different saturated and mono-unsaturated fatty acids differing in chain length were subjected to Ellman's assays to determine their ability to act as inhibitors for AChE or BChE. While the compounds were only very weak inhibitors of BChE, seven molecules were inhibitors of AChE holding IC50 = 4.3–12.8 M with three of them as significant inhibitors of this enzyme. The results have shown trans 2-mono-unsaturated fatty acids are better inhibitors for AChE than their saturated analogs. Furthermore, the screening results indicate that the chain length is crucial for obtaining an inhibitory efficacy. The best results were obtained for (2E) eicosenoic acid (14) showing inhibition constants Ki = 1.51 ± 0.09 M and Ki′ = 7.15 ± 0.55 M. All tested compounds were mixed-type inhibitors with a dominating competitive part. Molecular modelling calculations indicate a different binding mode of active/inactive compounds for the enzymes AChE and BChE.
Loesche, Anne,Wiemann, Jana,Al Halabi, Zayan,Karasch, Julia,Sippl, Wolfgang,Csuk, René
supporting information
p. 3315 - 3319
(2018/09/17)

Mild and versatile potassium fluoride/tetrabutylammonium fluoride protocol for ester hydrolysis
A mild and versatile protocol of potassium fluoride/tetrabutylammonium fluoride (KF/TBAF) in aqueous tetrahydrofuran for ester hydrolysis has been developed. The method is applied on variety of aliphatic and aromatic ester moieties bearing acid or base sensitive functional groups. The conditions have been also applied on acetates to yield alcohols. The chirality of optically pure esters remained intact with the conditions of the reaction.
Vijayalakshmi,Balakrishna,Mustafa, Shaik
p. 309 - 311
(2018/01/11)

Allyl-Palladium-Catalyzed α,β-Dehydrogenation of Carboxylic Acids via Enediolates
A highly practical and step-economic α,β-dehydrogenation of carboxylic acids via enediolates is reported through the use of allyl-palladium catalysis. Dianions underwent smooth dehydrogenation when generated using Zn(TMP)2?2 LiCl as a base in the presence of excess ZnCl2, thus avoiding the typical decarboxylation pathway of these substrates. Direct access to 2-enoic acids allows derivatization by numerous approaches.
Zhao, Yizhou,Chen, Yifeng,Newhouse, Timothy R.
supporting information
p. 13122 - 13125
(2017/09/13)

Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases
Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490?nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having a double bond at the α,β-position. These α,β-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decay rate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.
Brodl, Eveline,Ivkovic, Jakov,Tabib, Chaitanya R.,Breinbauer, Rolf,Macheroux, Peter
p. 1487 - 1495
(2017/02/18)

MANUFACTURING METHOD OF α,β-UNSATURATED CARBOXYLIC ACID
PROBLEM TO BE SOLVED: To provide a manufacturing method which can get α,β-unsaturated carboxylic acid at a high yield by liquid phase oxidation of α,β-unsaturated aldehyde by oxygen or air with a handy metal catalyst under a mild reaction condition. SOLUTION: Preferably under a presence of organic solvent, α,β-unsaturated carboxylic acid is manufactured by oxidation of α,β-unsaturated aldehydes and oxygen or air under a presence of an iron salt catalyst and a catalyst of alkali metal salt of carboxylic acid. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0050-0052

(2018/10/16)

Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds
A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.87.0 mM and 0.16.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.
Radivojevic, Jelena,Skaro, Sanja,Senerovic, Lidija,Vasiljevic, Branka,Guzik, Maciej,Kenny, Shane T.,Maslak, Veselin,Nikodinovic-Runic, Jasmina,OConnor, Kevin E.
p. 161 - 172
(2016/01/09)

A Strained Disilane-Promoted Carboxylation of Organic Halides with CO2 under Transition-Metal-Free Conditions
By using a strained four-membered ring disilane (3,4-benzo-1,1,2,2-tetraethyldisilacyclobutene) and CsF, a wide range of aryl, alkenyl, alkynyl, benzyl, allyl, and alkyl halides was successfully carboxylated under an ambient CO2 atmosphere (CO2 balloon) at room temperature within 2 h. In this carboxylation, a highly reactive silyl anion, which is generated from the disilane and CsF, is a key to facilitating the formation of a carbanion equivalent. The resulting anionic species can be trapped with CO2 to produce carboxylic acids with high efficiency.
Mita, Tsuyoshi,Suga, Kenta,Sato, Kaori,Sato, Yoshihiro
supporting information
p. 5276 - 5279
(2015/11/18)

Characterization of FabG and FabI of the Streptomyces coelicolor dissociated fatty acid synthase
Streptomyces coelicolor produces fatty acids for both primary metabolism and for biosynthesis of the secondary metabolite undecylprodiginine. The first and last reductive steps during the chain elongation cycle of fatty acid biosynthesis are catalyzed by FabG and FabI. The S. coelicolor genome sequence has one fabI gene (SCO1814) and three likely fabG genes (SCO1815, SCO1345, and SCO1846). We report the expression, purification, and characterization of the corresponding gene products. Kinetic analyses revealed that all three FabGs and FabI are capable of utilizing both straight and branched-chain β-ketoacyl-NAC and enoyl-NAC substrates, respectively. Furthermore, only SCO1345 differentiates between ACPs from both biosynthetic pathways. The data presented provide the first experimental evidence that SCO1815, SCO1346, and SCO1814 have the catalytic capability to process intermediates in both fatty acid and undecylprodiginine biosynthesis.
Singh, Renu,Reynolds, Kevin A.
p. 631 - 640
(2015/03/31)

Inhibition of human cytochrome P450 2E1 and 2A6 by aldehydes: Structure and activity relationships
The purpose of this study was to probe active site structure and dynamics of human cytochrome P4502E1 and P4502A6 using a series of related short chain fatty aldehydes. Binding efficiency of the aldehydes was monitored via their ability to inhibit the binding and activation of the probe substrates p-nitrophenol (2E1) and coumarin (2A6). Oxidation of the aldehydes was observed in reactions with individually expressed 2E1, but not 2A6, suggesting alternate binding modes. For saturated aldehydes the optimum chain length for inhibition of 2E1 was 9 carbons (KI = 7.8 ± 0.3 μM), whereas for 2A6 heptanal was most potent (KI = 15.8 ± 1.1 μM). A double bond in the 2-position of the aldehyde significantly decreased the observed KI relative to the corresponding saturated compound in most cases. A clear difference in the effect of the double bond was observed between the two isoforms. With 2E1, the double bond appeared to remove steric constraints on aldehyde binding with KI values for the 5-12 carbon compounds ranging between 2.6 ± 0.1 μM and 12.8 ± 0.5 μM, whereas steric effects remained the dominant factor in the binding of the unsaturated aldehydes to 2A6 (observed KI values between 7.0 ± 0.5 μM and >1000 μM). The aldehyde function was essential for effective inhibition, as the corresponding carboxylic acids had very little effect on enzyme activity over the same range of concentrations, and branching at the 3-position of the aldehydes increased the corresponding KI value in all cases examined. The results suggest that a conjugated π-system may be a key structural determinant in the binding of these compounds to both enzymes, and may also be an important feature for the expansion of the active site volume in 2E1.
Kandagatla, Suneel K.,Mack, Todd,Simpson, Sean,Sollenberger, Jill,Helton, Eric,Raner, Gregory M.
p. 195 - 202
(2014/07/21)

METHOD FOR THE DECARBOXYLATIVE HYDROFORMYLATION OF ALPHA, BETA- UNSATURATED CARBOXYLIC ACIDS
The present invention relates to a process for preparing aldehydes by reacting an α,β-unsaturated carboxylic acid or a salt thereof with carbon monoxide and hydrogen in the presence of a catalyst comprising at least one complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one compound of the formula (I), where Pn is pnicogen; W is a divalent bridging group having from 1 to 8 bridge atoms between the flanking bonds; R1 is a functional group capable of forming at least one intermolecular, noncovalent bond with the —X(═O)OH group of the compound of the formula (I); R2, R3 are each in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl or together with the pnicogen atom and together with the groups Y2 and Y3 if present form an optionally fused and optionally substituted 5- to 8-membered heterocycle; a, b and c are each 0 or 1; and Y1,2,3 are each, independently of one another, O, S, NRa or SiRbRc, where Ra,b,c are each H or in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; and the use of the above-described catalyst for the decarboxylative hydroformylation of α,β-unsaturated carboxylic acids.
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Page/Page column 8

(2011/02/25)

Combined transition-metal- and organocatalysis: An atom economic C3 homologation of alkenes to carbonyl and carboxylic compounds
A combination of regioselective room-temperature/ambient-pressure hydroformylation (transitionmetal catalysis) and decarboxylative Knoevenagel reactions (organocatalysis) allowed for the development of an efficient, one-pot C3 homologation of terminal alkenes to (E)-α,β-unsaturated acids and esters, (E)-β,γ-unsaturated acids, (E)-α-cyano acrylic acids, and α,β-unsaturated nitriles. All reactions proceed under mild conditions, tolerate a variety of functional groups, and furnish unsaturated carbonyl compounds in good yields and with excellent regioand stereocontrol. Further, an iterative C2 homologation of (E)-α,β-unsaturated carboxylic acids is possible through a combination of decarboxylative hydroformylation employing a supramolecular catalyst followed by decarboxylative Knoevenagel condensation with an organocatalyst.
Kemme, Susanne T.,Smejkal, Tomas,Breit, Bernhard
supporting information; experimental part
p. 3423 - 3433
(2010/06/21)

Palladium(II)-catalyzed selective oxidation of α,β-unsaturated aldehydes to α,β-unsaturated carboxylic acids with hydrogen peroxide
Palladium(II)-catalyzed chemoselective oxidation of αβ- unsaturated aldehydes with hydrogen peroxide to give Oα,β-unsaturated carboxylic acids was performed. Cinnamaldehyde was effectively catalyzed by palladium(II) trifluoroacetate to generate cinnamic acid in 92% yield under organic solvent-free conditions. The reaction appears to be applicable to various α,β-unsaturated aldehydes. Copyright
Kon, Yoshihiro,Imao, Daisuke,Nakashima, Takuya,Sato, Kazuhiko
supporting information; experimental part
p. 430 - 431
(2010/03/04)

A supramolecular catalyst for the decarboxylative hydroformylation of α,β-unsaturated carboxylic acids
(Chemical Equation Presented) Head 'em up, move 'em out, aldehyde! A catalytic transformation of α,β-unsaturated carboxylic acids into aldehydes through a hydroformylation-decarboxylation process has been developed (see scheme; Do = donor ligand, FG1 and FG2 = complementary functional groups). The reaction proceeds at mild conditions, tolerates many functional groups, and liberates CO2 as the only stoichiometric by-product.
Smejkal, Tomas,Breit, Bernhard
p. 3946 - 3949
(2008/12/23)

Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence
Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].
Kemme, Susanne T.,?mejkal, Tomá?,Breita, Bernhard
supporting information; experimental part
p. 989 - 994
(2009/05/27)

Total structure and inhibition of tumor cell proliferation of laxaphycins
From a mixed assemblage of Lyngbya majuscula rich marine cyanobacteria, we isolated a series of cell growth inhibitory cyclic peptides, The structures of the two major components, laxaphycins A (1) and B (2), and of two minor peptides, laxaphycins B2 (3) and B3 (4), were determined by spectroscopic methods and degradative analysis. Absolute configurations of natural and nonproteinogenic amino acids were determined by a combination of hydrolysis, synthesis of noncommercial residues, chemical derivatization, and HPLC analysis. The organism producing the laxaphycins was identified as the cyanobacterium Anabaena torulosa. The antiproliferative activity of laxaphycins was investigated on a panel of solid and lymphoblastic cancer cells. Our results demonstrate that in contrast to laxaphycin A, laxaphycin B inhibits the proliferation of sensitive and resistant human cancer cell lines and that this activity is strongly increased in the presence of laxaphycin A. This effect appears to be due to an unusual biological synergism.
Bonnard, Isabelle,Rolland, Marc,Salmon, Jean-Marie,Debiton, Eric,Barthomeuf, Chantal,Banaigs, Bernard
p. 1266 - 1279
(2007/10/03)

Mild zinc-promoted Horner-Wadsworth-Emmons reactions of diprotic phosphonate reagents
We report the development of a mild protocol for the Horner-Wadsworth- Emmons reaction of diprotic phosphonates that makes use of a zinc triflate promoter in the presence of mild ter-tiary amine bases to produce α,β-unsaturated carboxylic acids and amides. Georg Thieme Verlag Stuttgart.
Schauer, Douglas J.,Helquist, Paul
p. 3654 - 3660
(2008/03/13)

INHIBITORS OF YEAST FILAMENTOUS GROWTH AND METHOD OF THEIR MANUFACTURE
The invention broadly relates to the use of α, β-unsaturated fatty acids to inhibit the filamentous growth of fungi and yeasts and to a method for producing same. In particular the invention relates to the use of optionally substituted C8 to C15 α, β-unsaturated fatty acids or salts, esters or amides thereof for inhibiting or retarding the yeast-to-mycelium transition of organisms having a dimorphic life cycle.
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Page/Page column 12-14

(2008/06/13)

Cross coupling reactions of organozinc iodides with solid-supported electrophiles: Synthesis of 4-substituted benzoic and 3-substituted (E)- and (Z)-propenoic acids and amides
The solid-supported iodobenzoic acid derivatives 8-10 were coupled with a range of organozinc reagents 1-4 under palladium(o) catalysis. The coupled products released by acidic cleavage with TFA were obtained in high purities after recrystallization. Anal
Oates, Leslie J.,Jackson, Richard F.W.,Block, Michael H.
p. 140 - 144
(2007/10/03)

Magtrieve(TM): A new agent for the deprotection/oxidation of acetals and ketals under neutral conditions
Magtrieve(TM) can be used for the deprotection of acetals and ketals or for the direct oxidation to carboxylic acids under neutral conditions.
Ko, Kwang-Youn,Park, Sung-Tae
p. 6025 - 6027
(2007/10/03)

Total structure of hormothamnin A, a toxic cyclic undecapeptide from the tropical marine cyanobacterium hormothamnion enteromorphoides
The tropical marine cyanobacterium Hormothamnion enteromorphoides produces a suite of cytotoxic and antimicrobial cyclic peptides. The structure of the most lipophilic of these, hormothamnin A, was determined by interpretation of physical data, principally high NMR and FAB MS, in combination with chemical derivitization and degradation schemes. Isolation of a key pentapeptide fragment DPHE-D-LEU-L-ILE-D-allo-ILE-L-LEU, obtained under partial hydrolysis conditions, was instrumental to the final structure determination. β-D-aminooctanoic acid (D-BAOA) was characterized as a per-ester derivative following complete acid hydrolysis and Z-didehydrohomoalanine (DHHA) was spectroscopically in the intact peptide. The remaining residues (HYPRO, 2 × HSER, GLY) were evident from amino acid and spectroscopic analysis. Sequencing of these residues made use of knowledge from fragments, high field NMR (NOESY and ROESY) and FAB MS analysis of the intact peptide. Absolute stereochemistries of the α-amino residues were determined by HPLC analysis of the acid liberated residues derivatized with Marfey's reagent. The absolute stereochemistry of the β-amino residue was shown by circular dichoroism analysis, HPLC analysis of the Marfey derivative, and chiral synthesis of a homolog. By these techniques, hormothamnin A was demonstrated to possess a cyclo-[D-PHE-D-LEU-L-ILE-D-allo-ILE-L-LEU-GLY-D-BAOA-L-HSER-DHHAL-HYPRO-L-HSER] structure.
Gerwick, William H.,Jiang, Zhi D.,Agarwal, Santosh K.,Farmer, Bennett T.
p. 2313 - 2324
(2007/10/02)

Phenylsulphonamide substituted pyridinealkene- and aminooxyalkanecarboxylic acid derivatives
The compounds according to the invention can be prepared by reaction of the corresponding amines with sulphonic acid derivatives, or in the case of the aminooxy compounds by reaction of ketones with aminooxy compounds or alkylation of hydroxylamines, or in the case of the alkene compounds by reaction of ketones with phosphorusylides. The phenylsulphonamide substituted pyridinealkene- and -aminooxyalkenecarboxylic acid derivatives can be used for the treatment of thromboembolic disorders, ischaemias, arteriosclerosis, allergies and asthma.
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(2008/06/13)

Synthese und fluessigkristalline Eigenschaften 2,6-disubstituierter Naphtaline
The syntheses and the mesomorphic properties of a series of novel 2,6-disubstituted naphthalenes are described. 4-benzonitriles 5 and 4-benzonitriles 8 exhibit wide-range nematic mesophases. 6,6'-Di(n-Alkyl)-2,2'-binaphthyls 6 have been isolated as by-products from the reaction mixtures of 5.Some of these novel compounds have polymorphic properties.The esters 13 and 15 of 4-(6-hydroxy-2-naphthyl)benzonitrile show enhanced mesophase stabilities which reach maximum values in the series of α,β-unsaturated esters 15.The 4-(n-pentyl)benzoate 14 of the same (hydroxynaphthyl)benzonitrile has a melting point of 125 deg and a clearing point of > 310 deg.This particular derivative belongs to those liquid-crystalline compounds having the broadest purely nematic-phase range.In addition, (RS)-4-(2-pentyl-6-chromanyl)benzonitrile (20) and three compounds with two and four laterally arranged CN groups at the bicyclooctene, bicyclooctadiene, and phenyl-ring systems 31-33 were synthesized.Only 20 shows mesomorphic properties.
Lauk, Urs H.,Skrabal, Peter,Zollinger, Heinrich
p. 1406 - 1426
(2007/10/02)