60335-74-2Relevant academic research and scientific papers
The Intramolecular Silyl Modified Sakurai (ISMS) Reaction. A Simple and Versatile Synthesis of Tetrahydropyrans, Spiroethers, and Spiroketals
Marko, Istvan E.,Mekhalfia, Abdelaziz,Bayston, Daniel J.,Adams, Harry
, p. 2211 - 2213 (1992)
The Intramolecular Silyl Modified Sakurai (ISMS) reaction is a powerful tool for the construction of tetrahydropyrans, spiroethers, and spiroketals.The ISMS methodology was applied to a short and stereocontrolled synthesis of a minor component of the rectal gland secretion of the female Dacus oleae fruit fly.
Synthetic method of aromatic rose ether perfume
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Paragraph 0031-0042, (2020/07/24)
The invention discloses a synthesis method of an aromatic rose ether perfume, which comprises the following steps: with benzaldehyde and isopentenol as raw materials and non-strong protonic acid or Lewis acid as a catalyst, completely carrying out a reaction in an inert non-protonic solvent at reflux temperature, and carrying out after-treatment on the obtained reaction mixed solution to obtain 4-methyl-2-phenyl-dihydropyran. According to the method disclosed by the invention, a mild catalyst is adopted; benzaldehyde or isopentenol with the equivalent weight smaller than 1 is used, a solvent azeotropic with water is used for removing water generated in the reaction, the reaction selectivity is improved, and the reaction molar yield can reach about 90%; the method has the advantages of being economical, environmentally friendly, easy and convenient to implement and high in yield and is suitable for large-scale industrial production.
An efficient synthesis of dihydro- and tetrahydropyrans via oxonium-ene cyclization reaction
Bondalapati, Somasekhar,Reddy, Udagandla C.,Saha, Pipas,Saikia, Anil K.
experimental part, p. 3428 - 3438 (2011/06/20)
An efficient method has been developed for the synthesis of 2,3-dihydropyrans and 4-methylenetetrahydropyrans from aldehydes and substituted homoallyl alcohols in benzene mediated by boron trifluoride etherate in good yields. The reaction proceeds via oxonium-ene reaction.
SIMPLE AND EFFICIENT PREPARATION OF DIHYDROPYRANS AND SPIROKETALS USING THE INTRAMOLECULAR SILYL MODIFIED SAKURAI (ISMS) REACTION
Marko, Istvan E.,Bayston, Daniel J.,Mekhalfia, Abdelaziz,Adams, Harry
, p. 655 - 662 (2007/10/02)
Substituted tetrahydropyrans, spiroethers and spiroketals can be prepared in a single step using the ISMS reaction between the bis-silylated reagent 7b and aldehydes (acetals), ketones (ketals) and ortholactones respectively.This simple methodology was applied to the rapid synthesis of a pheromone containing a -spiroketal unit.
Regiocontrol in the intramolecular silyl modified Sakurai (ISMS) reaction. An efficient synthesis of a Dacus oleae fruit fly pheromone
Marko,Mekhalfia
, p. 1799 - 1802 (2007/10/02)
The ISMS reaction, which initially afforded a mixture of regioisomeric olefins, can now be controlled to produce only the exocyclic alkene. The ISMS methodology was used in a highly efficient synthesis of a Dacus oleae pheromone 8.
REACTIONS ON A SURFACE. 1. CONDENSATION OF 3-METHYL-3-BUTEN-1-OL WITH CARBONYL COMPOUNDS ON SiO2 AND Al2O3
Ibatullin, U. G.,Pavlov, Yu. V.,Safarov, M. G.
, p. 1107 - 1109 (2007/10/02)
3-Methyl-3-buten-1-ol reacts with various aldehydes and ketones on silica gel and Al2O3 surfaces in the absence of solvents and conventional catalysts for this reaction to form derivatives of di- and tetrahydropyrans.
REGIOSPECIFIC SYNTHESIS OF 2-SUBSTITUTED 4-METHYL-3,6-DIHYDRO-2H-PYRANS
Kazaryan, P. I.,Avakyan, O. V.,Avakyan, S. V.,Gevorkyan, A. A.
, p. 988 - 992 (2007/10/02)
The chloroalkylation of 3-halo-2-methyl-1-buten-4-ols was used to synthesize 4,5-dihalo-4-methyl-2-substituted tetrahydropyrans, which were converted regiospecifically to 3,6-dihydropyrans by reaction with magnesium.A similar reaction with zinc dust gave mixtures of 3,6- and 5,6-dihydropyrans.
EPOXIDATION OF 2-ARYL-4-METHYL-3,6-DIHYDROPYRANS AND REACTION OF THE PRODUCTS WITH PIPERIDINE
Ubatullin, U. G.,Syurina, L. V.,Vasil'eva, S. A.,Semenov, T. B.,Safarov, M. G.
, p. 1200 - 1202 (2007/10/02)
2-Aryl-4-methyl-4,5-epoxytetrahydropyrans, which react with piperidine regioselectively with trans-diaxial cleavage of the oxide ring at the least substituted carbon atom, were synthesized by the reaction of 2-aryl-4-methyl-3,6-dihydropyrans with peracids.
