10321-71-8Relevant articles and documents
Studies of unusual amino acids and their peptides. IX. The synthetic study of bottromycins B1 and B2
Yamada,Takashima,Miyazawa,et al.
, p. 878 - 883 (1978)
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Kaulen,Schaefer
, p. 513 (1979)
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Base-Catalyzed Reactions of α,β-Unsaturated Esters and Nitriles. 4. Dimerization of β-Alkyl-Substituted Acrylates
Shabtai, Joseph,Ney-Igner, Eva
, p. 3795 - 3802 (1981)
2-Butenoates 1-C4 alkyl, cyclohexyl, or 1-bornyl> and higher β-alkyl-substituted acrylates 2-C9 n-alkyl> undergo highly selective (>95percent) dimerization in the presence of promoted potassium or sodium catalysts to yield corresponding 2-alkylidene-3-alkylglutarates (3).The reaction involves metalation of the β-alkylacrylate at the C-2 position, followed by addition at C-3 of a second monomeric molecule.Changes in the relative extent of dimerization (Kr) as a function of structural and experimentalvariables were determined.Kr is strongly dependent upon the inductive and steric characteristics of the alcoholic (R) group and of the β-alkyl substituent (R').For an n-alkyl group as R' the Kr value increases with increase in chain length from C1 to C4 but then decreases for longer substituents (C5-C9).Among the two geometric isomers in the dimeric product 3, the isomer with an α-vinylic hydrogen cis to the carboalkoxy group is predominant in all cases, but its relative concetration decreases with an increase in the size of R'.Branched or cyclic β-substituents in 2 prevent dimerization due to steric hindrance in the rate-determining addition step.Promoted potassium or sodium catalysts show much higher dimerization activity compared to supported alkali metals or to alkoxides.For conversions of up to 60percent, Kr values in proton-exchanging alkylbenzene solvents and in nonexchanging alkylcyclohexanes are closely similar, indicating faster abstraction of an α-vinylic hydrogen from the monomer, rather than a benzylic hydrogen from the solvent, in the chain regeneration step of the reaction.
Synthesis of harringtonine, a Cephalotaxus antitumor alkaloid
Mikolajczak,Smith Jr.
, p. 4762 - 4765 (1978)
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MODIFIED KNOEVENAGEL CONDENSATIONS. SYNTHESIS OF (E)-3-ALKENOIC ACIDS.
Ragoussis, Nikitas
, p. 93 - 96 (1987)
Condensation of aliphatic aldehydes with a three molar excess of malonic acid and 0.001 mole piperidinium acetate in refluxing xylene, with continuous removal of the water formed, gave almost exclusively (E)-3-alkenoic acids, in good yield (60-85percent) and of high stereochemical purity (95-99percent).
Palladium-Catalyzed Low Pressure Carbonylation of Allylic Alcohols by Catalytic Anhydride Activation
Schelwies, Mathias,Paciello, Rocco,Pelzer, Ralf,Siegel, Wolfgang,Breuer, Michael
, p. 9263 - 9266 (2021)
A direct carbonylation of allylic alcohols has been realized for the first time with high catalyst activity at low pressure of CO (10 bar). The procedure is described in detail for the carbonylation of E-nerolidol, an important step in a new BASF-route to (?)-ambrox. Key to high activities in the allylic alcohol carbonylation is the finding that catalytic amounts of carboxylic anhydride activate the substrate and are constantly regenerated with carbon monoxide under the reaction conditions. The identified reaction conditions are transferrable to other substrates as well.
Enantioselective conjugate addition of a lithium ester enolate catalyzed by chiral lithium amides
Duguet, Nicolas,Harrison-Marchand, Anne,Maddaluno, Jacques,Tomioka, Kiyoshi
, p. 5745 - 5748 (2006)
(Diagram presented) Mixed aggregates of chiral lithium amide and lithium ester enolate have been employed in the enantioselective conjugate addition on α,β-unsaturated esters. Michael adducts were obtained in ee's up to 76% combining a lithium enolate and a chiral 3-aminopyrrolidine lithium amide. The sense of the induction was found to be determined by both the relative configuration of the stereogenic centers borne by the amide and the solvent in which the reaction was conducted.
COVALENT RAS INHIBITORS AND USES THEREOF
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Page/Page column 155, (2021/06/04)
The disclosure features compounds, or pharmaceutically acceptable salts thereof, alone and in combination with other therapeutic agents, pharmaceutical compositions, and protein conjugates thereof, capable of modulating biological processes including Ras, and their uses in the treatment of cancers.
METHOD FOR THE SYNTHESIS AND PRODUCTION OF ALKENYL COMPOUND
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Paragraph 0083, (2018/09/20)
PROBLEM TO BE SOLVED: To provide a method for producing an efficient alkenyl compound conveniently and inexpensively. SOLUTION: A first compound represented by formula (1) reacts with a second compound represented by formula (3), in the presence of amino acid, in solvent containing amine, in a range of 50-200°C, to produce an alkenyl compound represented by formula (A) [where R1 is hydrogen or an optionally substituted C1-C30 alkyl group, R2 is a carboxyl group or the like, R3 and R4 are hydrogen, an optionally substituted C1-C30 alkyl group or the like]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
