93293-37-9Relevant academic research and scientific papers
Synthesis route of 4-alkyl secondary amino-2-butanol compound
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Paragraph 0035-0036, (2020/12/30)
According to the invention, 4-hydroxy- 2-butanone is used as an initial raw material, the 4-alkyl secondary amino -2-butanol compound is prepared through sulfonyl chloride reagent substitution reaction, reduction reaction and organic amine ammonolysis reaction, and the novel synthetic route solves the problems of many byproducts, low yield, expensive raw materials, toxicity, harmlessness and the like in the prior art. Compared with the prior art, the method is low in raw material cost, stable and mild in reaction, few in reaction byproducts, high in yield, environmentally friendly and suitablefor synthesis of a series of organic matters. Meanwhile, an amplification test is passed through the technology disclosed by the invention, and a good application prospect is achieved.
A formal anti-Markovnikov hydroamination of allylic alcohols via tandem oxidation/1,4-conjugate addition/1,2-reduction using a Ru catalyst
Nakamura, Yushi,Ohta, Tetsuo,Oe, Yohei
supporting information, p. 7459 - 7462 (2015/05/04)
A formal anti-Markovnikov hydroamination of allylic alcohols using a Ru catalyst via tandem oxidation/1,4-conjugate addition/1,2-reduction was developed. Thus, the reaction of allylic alcohols with amines was performed in the presence of the catalyst generated from RuClH(CO)(PPh3)3 and 2,6-bis(n-butyliminomethyl)pyridine in situ to afford the corresponding γ-amino alcohols efficiently. This journal is
Amine-directed hydroboration: Scope and limitations
Scheideman, Matthew,Wang, Guoqiang,Vedejs, Edwin
supporting information; experimental part, p. 8669 - 8676 (2009/02/03)
Iodine activation induces intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent control of regiochemistry compared to control experiments using excess THF?BH3. Deuterium labeling and other evidence confirm that the iodine-induced hydroboration reaction of homoallylic amine boranes occurs via an intramolecular mechanism equivalent to the classical 4-center process and without competing retro-hydroboration. Longer carbon chain tethers result in lower regioselectivity, whereas the shorter tether in allylic amines results in a switch to dominant intermolecular hydroboration. Regioselectivity in THF?BH3 control experiments is higher for the allylic amine boranes compared to the iodine activation experiments, whereas the reverse is true for homoallylic amine borane activation.
A mechanistic alternative for the intramolecular hydroboration of homoallylic amine and phosphine borane complexes
Scheideman, Matthew,Shapland, Peter,Vedejs, Edwin
, p. 10502 - 10503 (2007/10/03)
Intramolecular hydroboration is demonstrated starting from homoallylic amine boranes upon activation by iodine. The process involves a B-iodoborane complex as the intermediate and may occur via internal displacement of iodide by the alkene to generate a cationic borane-alkene π-complex on the way to hydroboration products. The reaction can be carried out using a catalytic amount of iodine. Copyright
Structure - Immunosuppressive activity relationships of new analogues of 15-deoxyspergualin. 2. Structural modifications of the spermidine moiety
Lebreton, Luc,Jost, Eric,Carboni, Bertrand,Annat, Jocelyne,Vaultier, Michel,Dutartre, Patrick,Renaut, Patrice
, p. 4749 - 4763 (2007/10/03)
A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine 'D' region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene α to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60c which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.
