61638-81-1Relevant academic research and scientific papers
Synthesis method of 2-(1-cyclohexenyl) ethylamine
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Paragraph 0044-0046, (2020/11/02)
The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of a compound 2-(1-cyclohexenyl) ethylamine (I). Cyclohexanone (II) and a Grignard reagent are subjected to a Grignard reaction in an organic solvent to be converted into 1-vinyl cyclohexanol (III), the 1-vinyl cyclohexanol (III) and a chlorination reagent are subjected to a chlorination/rearrangement one-pot reaction in an organic solvent in the presence of organic alkali to prepare (2-chloroethylene methylene) cyclohexane (IV), the (2-chloroethylene methylene) cyclohexane (IV) and urotropine are subjected to quaternization in an organic solvent to form N-cyclohexylidene ethyl urotropine hydrochloride (V), and finally, hydrolysis rearrangement is carried out in a solvent in the presence of inorganic mineral acid to obtain the 2-(1-cyclohexenyl) ethylamine (I). The compound (I) has important industrial application value as an intermediate for synthesizing the antitussive drug dextromethorphan hydrobromide. The method has the advantages of cheap and accessible raw materials, mild reaction conditions, high yield and high product purity, is simple to operate, and is convenient for industrial production.
Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution
Ardolino, Michael J.,Morken, James P.
supporting information, p. 7092 - 7100 (2014/06/09)
Under the influence of a chiral bidentate diphosphine ligand, the Pd-catalyzed asymmetric cross-coupling of allylboron reagents and allylic electrophiles establishes 1,5-dienes with adjacent stereocenters in high regio-and stereoselectivity. A mechanistic study of the coupling utilizing reaction calorimetry and density functional theory analysis suggests that the reaction operates through an inner-sphere 3,3′-reductive elimination pathway, which is both rate-defining and stereodefining. Coupled with optimized reaction conditions, this mechanistic detail is used to expand the scope of allyl-allyl couplings to allow the generation of 1,5-dienes with tertiary centers adjacent to quaternary centers as well as a unique set of cyclic structures.
Enantioselective intramolecular aldehyde α-alkylation with simple olefins: Direct access to homo-ene products
Comito, Robert J.,Finelli, Fernanda G.,Macmillan, David W. C.
supporting information, p. 9358 - 9361 (2013/07/26)
A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde-olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings with alkene transposition. Conceptually, this novel mechanism allows direct access to "homo-ene"-type products.
A novel one-pot conversion of allyl alcohols into primary allyl halides mediated by acetyl halide
Kishali, Nurhan,Polat, M. Fatih,Altundas, Ramazan,Kara, Yunus
, p. 67 - 72 (2008/09/17)
A new and simple method for the synthesis of the primary allyl chlorides and bromides 9-16 from the secondary or tertiary allyl alcohols 3-8 and acyl halide was developed (Scheme 2, Table 1). Non-commercially available secondary and tertiary allyl alcohols were synthesized from the related ketones and aldehydes via the addition of vinylmagnesium chloride. Mechanistic studies indicate that the alcohols were first acetylated by the acetyl halide and then protonated prior to substitution by the halide, Cl- or Br -, via an 5N2′ reaction, to yield the primary halides (Scheme 5).
