29541-97-7Relevant academic research and scientific papers
Pheromone components of the wheat stem sawfly: Identification, electrophysiology, and field bioassay
Cosse, Allard A.,Bartelt, Robert J.,Weaver, David K.,Zilkowski, Bruce W.
, p. 407 - 423 (2002)
Volatiles collections and cuticular extracts of the wheat stem sawfly, Cephus cinctus Norton (Hymenoptera: Cephidae), were analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) in order to detect possible pheromone components of
ISOLATION AND IDENTIFICATION OF A SUPPLEMENTARY COMPONENT OF THE SEX PHEROMONE OF Mamestra brassicae FEMALES
Nedopekina, S. F.,Kovalev, B. G.,Khlebnikov, V. A.
, p. 220 - 222 (1986)
Using gas-liquid chromatography and mass spectrometry, from an extract of the sex pheromone of females of the cabbage moth Mamestra brassicae L. an additional component of the pheromone has been isolated and identified - heptadec-cis-11-en-1-ol acetate.
Method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate
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, (2020/06/16)
The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate. According to the method, malonic acid and 9-bromo-1-nonyl alcohol are used as two starting raw materials. The method comprises the following steps: carrying out a Knoevenagel condensation reaction on malonic acid and propionaldehyde inthe presence of piperidine acetate to generate (E)-3-pentenoic acid, then carrying out lithium aluminum hydride reduction to obtain (E)-3-penten-1-ol, carrying out bromination reaction, and refluxingwith triphenylphosphine in acetonitrile to obtain (E)-3-pentenyltriphenylphosphine bromide; carrying out a PCC oxidation reaction on 9-bromo-1-nonanol to obtain 9-bromononanal, and then reacting the 9-bromononanal with potassium acetate to obtain 9-acetoxynonanal; and finally, carrying out a Wittig reaction on (E)-3-pentenyltriphenylphosphine bromide and 9-acetoxynonanal so as to obtain (9Z, 12E)-9,12-tetradecadien-1-ol acetate. An E-type double bond is constructed by utilizing the Knoevenagel condensation reaction of malonic acid and propionaldehyde, and the method has the advantages of mildreaction conditions, environmental friendliness, simple synthetic route and the like.
Nucleoside analogues with a 1,3-diene-Fe(CO)3 substructure: Stereoselective synthesis, configurational assignment, and apoptosis-inducing activity
Hirschh?user, Christoph,Velcicky, Juraj,Schlawe, Daniel,Hessler, Erik,Majdalani, André,Neud?rfl, J?rg-Martin,Prokop, Aram,Wieder, Thomas,Schmalz, Hans-Günther
supporting information, p. 13017 - 13029 (2013/10/01)
The synthesis and stereochemical assignment of two classes of iron-containing nucleoside analogues, both of which contain a butadiene-Fe(CO)3 substructure, is described. The first type of compounds are Fe(CO)3-complexed 3'-alkenyl-2′,3′-dideoxy- 2′,3′-dehydro nucleosides (2,5-dihydrofuran derivatives), from which the second class of compounds is derived by formal replacement of the ring oxygen atom by a CH2 group (carbocyclic nucleoside analogues). These compounds were prepared in a stereoselective manner through the metal-assisted introduction of the nucleobase. Whilst the furanoid intermediates were prepared from carbohydrates (such as methyl-glucopyranoside), the carbocyclic compounds were obtained by using an intramolecular Pauson-Khand reaction. Stereochemical assignments based on NMR and CD spectroscopy were confirmed by X-ray structural analysis. Biological investigations revealed that several of the complexes exhibited pronounced apoptosis-inducing properties (through an unusual caspase 3-independent but ROS-dependent pathway). Furthermore, some structure-activity relationships were identified, also as a precondition for the design and synthesis of fluorescent and biotin-labeled conjugates. I gotta Fe-ling: Iron-containing nucleoside analogues, which were first synthesized during an exercise in stereoselective π-complex chemistry, exhibited pronounced cytotoxic and apoptosis-inducing activities, even against resistant cancer cell lines. Both hetero- (X=O) and carbocyclic (X=CH2) compounds were studied, and a synthetic route to R′-labeled derivatives was developed as a precondition for future biological experiments. TDS=thexyldimethylsilyl. Copyright
Tandem application of C-C bond-forming reactions with reductive ozonolysis
Willand-Charnley, Rachel,Dussault, Patrick H.
, p. 42 - 47 (2013/03/29)
Several variants of reductive ozonolysis, defined here as the in situ generation of aldehydes or ketones during ozonolytic cleavage of alkenes, are demonstrated to work effectively in tandem with a number of C-C bond-forming reactions. For reactions involving basic nucleophiles (1,2- addition of Grignard reagents, Wittig or Horner-Emmons olefinations, and directed aldol reactions of lithium enolates), the one-pot process offers a rapid and high-yielding alternative to traditional two-step protocols.
Pyridine is an organocatalyst for the reductive ozonolysis of alkenes
Willand-Charnley, Rachel,Fisher, Thomas J.,Johnson, Bradley M.,Dussault, Patrick H.
supporting information; experimental part, p. 2242 - 2245 (2012/06/30)
Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.
A mild one-pot conversion of alkenes into amines through tandem ozonolysis and reductive amination
Kyasa, Shivakumar,Fisher, Thomas J.,Dussault, Patrick H.
experimental part, p. 3475 - 3481 (2011/12/04)
The selective reduction of hydroperoxyacetals to aldehydes by sodium triacetoxyborohydride provides the basis for a mild one-pot synthesis of amines from alkenes. Georg Thieme Verlag Stuttgart.
Facile synthesis of mill moth's sex pheromone components
Hornyanszky, Gabor,Rohaly, Janos,Novak, Lajos
, p. 1533 - 1540 (2008/09/20)
An improved method for the preparation of mill moth's sex pheromone components in high diastereomeric purity is described. Copyright Taylor & Francis Group, LLC.
Ozonolysis in solvent/water mixtures: Direct conversion of alkenes to aldehydes and ketones
Schiaffo, Charles E.,Dussault, Patrick H.
, p. 4688 - 4690 (2008/09/21)
(Chemical Equation Presented) Ozonolysis of alkenes in the presence of solubilized water results in the direct formation of aldehydes and/or ketones, avoiding the need to isolate or decompose ozonides.
Synthesis of 10-hydroxy- and 9-oxo-2E-decenoic acids from oleic acid
Kharisov,Botsman,Botsman,Ishmuratova,Ishmuratov,Tolstikov
, p. 145 - 148 (2007/10/03)
A practical synthesis of biologically active 10-hydroxy- and 9-oxo-2E-decenoic acids, components of mandibular gland secretion of honeybee (Apis mellifera L.), is developed using ozonolysis - reduction of oleic acid and 1,9-diacetoxynon-1-ene in the key steps.
