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Kharisov, R. Ya.; Botsman, O. V.; Botsman, L. P.; Ишмуратова, Н. М.; Ishmuratov, G. Yu.; Толстиков, Г. А.

doi:10.1023/a:1019683830012

Cited by 11 publications

(9 citation statements)

References 4 publications

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“…Moreover, it can be used on a large scale. Indeed, Doebner-Knoevenagel reaction has been widely reported for the synthesis of 10-HDA 5,7,8 . However, literature is quite ambiguous.…”

Section: Scheme 3 Preparation Of Aldehydementioning

confidence: 99%

“…3 As a result, in recent years, several synthetic approaches for 10-HDA 9-ODA have been reported. [4][5][6][7][8] However, in general these methodologies employ expensive and toxic reagents, or require procedures that are difficult to handle on a large scale. In this work, we report for the first time a cost-effective and metal-free strategy for the selective preparation of compounds 1 and 2 in multigram scale.…”

Section: Introductionmentioning

confidence: 99%

“…3 As a result, in recent years, several synthetic approaches for 10-HDA and 9-ODA have been reported. [4][5][6][7][8] However, in general these methodologies employ expensive and toxic reagents, or require procedures that are difficult to handle on a large scale.…”

Section: Introductionmentioning

confidence: 99%

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Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

et al. 2012

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Abstract10-hydroxy-2E-decenoic (10-HDA) and 9-oxo-2E-decenoic (9-ODA) acids, two components identified in honeybees secretions, have both received considerable recent interest due to their involvement in caste switch and maintenance. Herein we report for the first time a metal-free, gram scale, and stereoselective synthesis of these honeybee secretion components by TEMPO catalyzed oxidation of readily available alcohols and subsequent Doebner-Knoevenagel reaction between the resulting aldehydes and malonic acid. Mechanistic investigations undertaken highlighted the crucial role of the Doebner-Knoevenagel reaction in the high yielding and selective preparation of the α,β-unsaturated acids 10-HDA and 9-ODA.The combination of inexpensive and environmental friendly reagents with simple synthetic procedures render this approach a valuable green strategy for the gram scale preparation of these biologically relevant natural molecules. Graphical abstract

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“…Moreover, it can be used on a large scale. Indeed, Doebner-Knoevenagel reaction has been widely reported for the synthesis of 10-HDA 5,7,8 . However, literature is quite ambiguous.…”

Section: Scheme 3 Preparation Of Aldehydementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

et al. 2012

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“…The reduction with dimethyl sulfide [5,6], potassium iodide [7], hydrogen on palladium black [4] or on catalyst Pd/CaCO 3 [8] provides 9-oxononanoic acid and nonanal. A preparation was described of 9-(hydroxyimino)nonanoic acid 4 from sodium oleate at the use of hydroxylamine in water [9,10].…”

mentioning

confidence: 99%

“…At the reduction with semicarbazide hydrochloride a mixture formed of the same methyl esters 5 and 7, and also 1,1-dimethoxynonane 9 and methyl 9,9-dimethoxynonanоate 10 (Scheme 1). The latter is an intermediate product in the synthesis of biologically and pharmacologically active (2Е)-9-oxo-and 10hydroxydec-2-enoic acids, components of royal jelly of honeybees Apis mellifera L. [6].…”

mentioning

confidence: 99%

Transformations of peroxide products of oleic acid ozonolysis at treatment with hydroxylamine and semicarbazide hydrochlorides

et al. 2015

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Peroxide products of oleic acid ozonolysis treated with semicarbazide and hydroxylamine hydrochlorides in methanol are predominantly converted into methyl nonanoate and dimethyl nonanedioate, in 2-propanol, into isopropyl nonanoate and monoisopropyl ester of nonanedioic acid, and also into nonanenitrile, in tetrahydrofuran and in a mixture of acetic acid with dichloromethane, into nonanoic and nonanedioc acids, and also in nonanal oxime and 9-(hydroxyimino)nonanoic acid.Oleic [(9Z)-octadec-9-enoic] acid 1 is present in the composition of nearly all natural fats and oils. One of its main sources is olive (~80%), and also sunflower (39%) and cottonseed (35%) oils, in animal fats it constitutes 36-45% of the overall amount of fatty acids [1].

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Practical Synthesis of (E)‐α,β‐Unsaturated Carboxylic Acids Using a One‐Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence

2008

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Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, onepot procedure for the synthesis of (E)-a,b-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-a,b-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].

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Cited by 11 publications

References 4 publications

Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

Transformations of peroxide products of oleic acid ozonolysis at treatment with hydroxylamine and semicarbazide hydrochlorides

Practical Synthesis of (E)‐α,β‐Unsaturated Carboxylic Acids Using a One‐Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence

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