55944-70-2Relevant articles and documents
Short and Easily Scalable Synthesis of the Sex Pheromone of the Horse-Chestnut Leaf Miner (Cameraria ohridella) Relying on a Key Ligand- And Additive-Free Iron-Catalyzed Cross-Coupling
Chourreu, Pablo,Gayon, Eric,Guerret, Olivier,Guillonneau, Lo?c,Lefèvre, Guillaume
, p. 1335 - 1340 (2020)
We describe in this work a short six-step convergent high-scale synthesis of the sex pheromone of the horse-chestnut leaf miner ((8E,10Z)-tetradeca-8,10-dienal). This procedure relies on a key stereoselective iron-catalyzed Kumada cross-coupling, which affords the coupling product in high yield in the absence of additional ligands or additives. DFT calculations moreover suggest that ω-alkoxide groups on iron-ligated chains in transient organoiron(II) intermediates can enhance their stability and hamper their decomposition in off-cycle β-hydride elimination reactions.
Cu-Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One-Carbon-Extended Alcohols
Zhao, Siling,Mankad, Neal P.
supporting information, p. 5867 - 5870 (2018/04/17)
We have developed a reductive carbonylation method by which unactivated alkyl iodides can be hydroxymethylated to provide one-carbon-extended alcohol products under Cu-catalyzed conditions. The method is tolerant of alkyl β-hydrogen atoms, is robust towards a wide variety of functional groups, and was applied to primary, secondary, and tertiary alkyl iodide substrates. Mechanistic experiments indicate that the transformation proceeds by atom-transfer carbonylation (ATC) of the alkyl iodide followed in tandem by two CuH-mediated reductions in rapid succession. This radical mechanism renders the Cu-catalyzed system complementary to precious-metal-catalyzed reductive carbonylation reactions.
A furan or tetrahydrofuran by the green primary alcohol derivatives for the preparation of the new method
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Paragraph 0012; 0013; 0015; 0018, (2017/02/17)
The invention provides a novel method for preparing middle/long-chain primary alcohol from furan or tetrahydrofuran derivatives. Specifically, a double-function catalyst is adopted, and such catalyst comprises two activity centers, namely, a hydrogenation activity center and an acid center; water is taken as a solvent in the reaction, the reaction is carried out in a batch reactor, and by utilizing the characteristic that the middle/long-chain primary alcohol is not dissolved in water, the generated primary alcohol is naturally separated from water and the catalyst, and alkane is prevented from being generated because of hydrogen over-addition or hydrogenolysis. Due to the characteristic that the primary alcohol and the water are not dissolved with each other, the primary alcohol can be conveniently separated, the separation cost is greatly lowered, and good industrial prospect is achieved.
Oxidation of monohydric and dihydric alcohols with CCl4 catalyzed by molybdenum compounds
Khusnutdinov,Shchadneva,Burangulova,Muslimov,Dzhemilev
, p. 1615 - 1621 (2007/10/03)
Mo(CO)6 catalyzed oxidation of alcohols and diols with tetrachloromethane. Primary oxidation products in reaction of alcohols with CCl4 are alkyl hypochlorites, and final products depending on the structure of initial alcohol are aldehydes (as acetals), ketones, chloroketones, and esters.
Ethynylation of the ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamide complex
Karpinska,Lewandowska,Grodner
, p. 937 - 942 (2007/10/03)
A new operationally simple and highly efficient procedure for the ethynylation of ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamine complex in N,N-dimethylacetamide is described.
The synthesis of polyunsaturated α,ω-dicarboxylic acids. I. Chemical synthesis of octadecadienedioic acids regioisomeric in double bond positions
Ivanov,Groza,Mal'chenko,Myagkova,Shewe
, p. 481 - 487 (2007/10/03)
Novel compounds, (6Z,9Z)-octadecadienedioic acid, its regioisomers in double bond positions, and their acetylenic precursors, were synthesized. A general approach to the synthesis of a series of ω-hydroxyacetylenic acids in the context of a unique synthetic scheme was suggested.
19→nor→steroids
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, (2008/06/13)
Novel 19-nor-steroids of the formula STR1 wherein the A and B rings have a structure selected from the group consisting of STR2 having hormonal properties and their preparation and intermediates.
REGIOSPECIFIC AND STEREOSPECIFIC SUBSTITUTION OF HYDROXYL IN ALIPHATIC ALCOHOLS BY HALOGEN
Matveeva, E. D.,Kurts, A. L.,Yalovskaya, A. I.,Nikishova, N. G.,Bundel', Yu. G.
, p. 642 - 646 (2007/10/02)
A new system containing triphenylphosphine and trichloro- and tribromoacetic ester makes it possible to substitute the hydroxyl group in alcohols by halogen.Regiospecific and stereospecific substitution of the hydroxyl by the halogen takes place as a result of the reaction of primary and secondary aliphatic alcohols and of 2-alkenols, susceptible to isomerization processes, with this system.