74882-16-9Relevant articles and documents
Total synthesis of the biphenyl alkaloid (-)-lythranidine
Gebauer, Konrad,Fuerstner, Alois
, p. 6393 - 6396 (2014)
A sequence comprising a ring-closing alkyne metathesis of a propargyl alcohol derivative, followed by a ruthenium-catalyzed redox isomerization of the derived cycloalkyne and a transannular aza-Michael addition allowed the formation of the distinguishing
Method for synthesizing 1, 7-2-(4-hydroxy phenyl)-heptane-1, 4-diene-3-ketone
-
Paragraph 0043; 0051-0052; 0067-0068, (2018/04/03)
The invention relates to the field of pharmaceutical synthesis, in particular to a method for synthesizing 1,7-2-(4-hydroxy phenyl)-heptane-1,4-diene-3-ketone. The method, selecting 3-(4- hydroxy phenyl)propionic acid and 4-hydroxybenzaldehyde as raw materials, includes (1), subjecting the 3-(4-hydroxy phenyl)propionic acid to esterification, methyl protection, reduction and oxidation to obtain 3-(4-(methoxy methyl)phenyl)propionaldehyde; (2), subjecting the 4-hydroxybenzaldehyde to etherification and aldol reaction to obtain 4-(4-((methoxy methyl)phenyl)butyl-3-alkene-2-ketone; (3), subjecting the 4-(4-((methoxy methyl)phenyl) butyl-3-alkene-2-ketone and the 3-(4-(methoxy methyl)phenyl)propionaldehyde to aldol condensation, and allowing the reactor to react with hydrochloric acid to obtain 1, 7-2-(4-hydroxy phenyl)-heptane-1,4-diene-3-ketone. The method has the advantages of simplicity, easiness in operation, high yield and high purity.
Reaction of Aryl and Vinyl Halides with Zerovalent Nickel-Preparative Aspects and the Synthesis of Alnusone
Semmelhack, M.F.,Helquist, Paul,Jones, L.D.,Keller, Leonard,Mendelson L.,et al.
, p. 6460 - 6471 (2007/10/02)
Zerovalent nickel complexes such as bis(1,5-cyclooctadiene)nickel and tetrakis(triphenylphosphine)nickel react rapidly with aryl and vinyl halides to produce the symmetrical coupling products, a low-temperature analogue of the Ullman reaction.The reaction proceeds through oxidative addition of the organic halide to Ni(0), and the reactivity of the Ni(II)intermediates has been examined.Arylnickel halide complexes decompose rapidly to biaryls in DMF.The coupling of simple vinyl halides proceeds with isomerization of the double bond but 3-haloacrylates give efficient co upling with retention of geometry.Cyclizations to form ortho-bridged biaryls are efficient in simple cases (6-, 7-, 8-, 9-, 10-, and 14-membered rings) but fail with an ortho-disubstituted case.The 13-membered meta-bridged cyclic biphenyl, alnusone, is prepared efficiently with the crucial aryl halide coupling to form the ring proceeding in 50percent yield.A side reaction promoted by the presence of protons and with certain ortho-substituted aryl halides is reduction of the aryl halide to the arene.This process can be enhanced by deliberate addition of acid during reaction with Ni(0) and a series of aryl halides underwent succesful reduction.
