34597-73-4

Upstream product

• 100-52-7 benzaldehyde 
• 5053-63-4 3-amino-1-phenylpropan-1-ol 
• 98-86-2 acetophenone 
• 936-59-4 3-chloropropiophenone 
• 25039-19-4 (E)-3-morpholino-1-phenyl-2-propen-1-one 
• 100-46-9 benzylamine 
• 93-54-9 1-Phenyl-1-propanol 
• 56570-47-9 (Z)-3-(benzylamino)-1-phenylprop-2-en-1-one 
• 14371-10-9 (E)-3-phenylpropenal 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 103-49-1 dibenzylamine 
• 768-03-6 Phenyl vinyl ketone 
• 122377-71-3 3-(N,N-Dibenzylamino)-1-phenyl-propan-1-on 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 

Downstream Products

• 40032-55-1 N-cinnamylbenzylamine 
• 252353-91-6 4-[benzyl-(3-hydroxy-3-phenyl-propyl)-amino]-butyronitrile 
• 1215021-58-1 3-benzyl-6-phenyl 1,2,3-oxathiazinane 2,2-dioxide 
• 181474-66-8 5-[Benzyl-(3-chloro-3-phenyl-propyl)-amino]-4-chloro-2-methyl-2H-pyridazin-3-one 
• 252353-77-8 C₄₅H₇₁N₇O₉ 
• 252353-67-6 {4-[benzyl-(3-tert-butoxycarbonylamino-3-phenyl-propyl)-amino]-butylcarbamoyloxy}-acetic acid methyl ester 
• 252353-73-4 {4-[benzyl-(3-tert-butoxycarbonylamino-3-phenyl-propyl)-amino]-butylcarbamoyloxy}-acetic acid 
• 252353-95-0 {3-[(4-amino-butyl)-benzyl-amino]-1-phenyl-propyl}-carbamic acid tert-butyl ester 
• 252353-94-9 {3-[benzyl-(3-cyano-propyl)-amino]-1-phenyl-propyl}-carbamic acid tert-butyl ester 
• 252353-92-7 methanesulfonic acid 3-[benzyl-(3-cyano-propyl)-amino]-1-phenyl-propyl ester 
• 252353-93-8 4-[(3-azido-3-phenyl-propyl)-benzyl-amino]-butyronitrile 
• 181474-62-4 5-[Benzyl-(3-hydroxy-3-phenyl-propyl)-amino]-4-chloro-2-methyl-2H-pyridazin-3-one 

Relevant academic research and scientific papers

Catalytic asymmetric alkylation reactions for the construction of protected ethylene-amino and propylene-amino motifs attached to quaternary stereocentres

An efficient catalytic and stereoselective method for the direct construction of protected ethylene-amino and propylene-amino scaffolds attached to quaternary stereocentres is reported. Preliminary investigations revealed a mild base catalysed nucleophilic ring opening of N-sulfonyl aziridines using the commercially available phosphazene base 2-tert-butylimino-2-diethylamino-1,3- dimethyl-perhydro-1,3,2-diazaphosphorine (BEMP) was possible and resulted in highly efficient alkylation reactions with a range of methine carbon acids. This reaction could be rendered highly asymmetric (up to 97 % ee) by employing phase-transfer catalysis to control stereoinduction. Incorporation of alkyl substituents onto the aziridine electrophile, resulted in a highly diastereoselective (up to 30:1 d.r.) variant of this methodology. A further extension using N-protected cyclic sulfamidates as the electrophilic component was successful with a range of pro-nucleophiles (up to 96 % ee and 45:1 d.r.) and allowed a range of nitrogen protecting groups (carbamate, sulfonyl, phosphonyl, benzyl) to be incorporated into the alkylation adducts. Finally, the utility of the products have been demonstrated in the synthesis of useful heterocycles and compounds bearing structural components of natural products. Open sesame: The enantio- and diastereoselective nucleophilic ring opening of protected aziridines and cyclic sulfamidates using asymmetric phase-transfer catalysis (PTC) is reported. The ring-opening alkylation reactions create quaternary chiral centres containing ethylene- and propylene-amino motifs in good yields with good to excellent enantioselectivities (see scheme). These reactions are broad in scope and a wide range of pro-nucleophiles are tolerated. Copyright

Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence

An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β- unsaturated imine formation, β-boration, reduction (CN) and oxidation (C-B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added to directly access the corresponding 1,3-oxazine derivatives.

Transformation of α-substituted propanols into γ-amino alcohols through nickel-catalyzed amination on the terminal γ-carbon of propanols

A nickel-phosphine complex was found to be effective as the catalyst for the transformation of alcohols into β-enaminones, which was successively converted into γ-amino alcohols by a conventional reductant. The sequential transformation is equivalent to the carbon-nitrogen bond formation at the γ-position of saturated alcohols. Georg Thieme Verlag Stuttgart · New York.

Catalytic enantio- and diastereoselective alkylations with cyclic sulfamidates

(Figure Presented) Open for business: The enantio- and diastereoselective nucleophilic ring opening of five-membered and six-membered cyclic sulfamidates under asymmetric phase-transfer catalysis is presented. A range of pro-nucleophiles have been successfully alkylated in good yields and in good to excellent enantioselectivites.

Practical synthesis of enantiopure γ-amino alcohols by rhodium-catalyzed asymmetric hydrogenation of β-secondary-amino ketones

(Chemical Equation Presented) Another way to antidepressants: A series of β-secondary-amino ketone hydrochlorides (e.g. 1) were hydrogenated with remarkably high enantioselectivities by using a Rh complex containing P-chiral bisphospholane 2. These results establish a short and practical means for the synthesis of enantiopure N-monosubstituted γ-amino alcohols (e.g. 3), which are key intermediates in the synthesis of important antidepressants. (nbd = norbornadiene; TON = turnover number).

Synthesis and preliminary biological characterization of a new potential 125I-radioligand for dopamine and serotonin receptors

The synthesis and a preliminary biological characterization of a new class of N-benzyl-aminoalcohols which have serotonin (5-HT2) and dopamine (D2) receptor affinity is described. In vitro competition binding studies were conducted with the new molecules and 3H-spiperone on crude membrane preparation from rat striatum and frontal cortex. One of these compounds, 3-benzylamino-1-(4-fluoro-2-iodophenyl)-propan-1-ol (6f), whose IC50 values are in the micromolar range for both the D2 and 5-HT2 receptors, was prepared in iodine-125 labelled form (6i) by nucleophilic substitution of the bromine atom of 3-benzylamino-1-(2-bromo-4-fluorophenyl)-propan-1-ol (6d). In the in vivo studies, conducted on rats, the radiolabelled molecule 6i shows a good capacity to cross the blood-brain barrier (BBB) with a mean value of first pass cerebral extraction (E) of ca. 50% when the regional cerebral blood flow, measured with microsphere technique, is in the experimental animal's physiologic range (0.8-1 mL/min/g). A preliminary in vitro autoradiographic distribution on coronal rat brain slices of the radioiodinated molecule showed that it was preferentially localized in the striatum and in the cerebral regions rich in dopamine- and serotonin receptors, even if a high non-specific binding was observed.

Solid-phase synthesis of arylalkanolamines

A versatile method for the solid-phase synthesis of differentially substituted arylalkanolamines has been developed using immobilized carbamates. The method has been successfully used for the synthesis of arylethanolamines and arylpropanolamines in high yields and purities.

Structure - Immunosuppressive activity relationships of new analogues of 15-deoxyspergualin. 2. Structural modifications of the spermidine moiety

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.

Synthesis of some novel 2-phenylpyridazino[4,5-b][1,5]thiazepines

Synthesis of some derivatives of the pyridazino[4,5-b][1,5]thiazepine ring system is reported. Thus, 5-benzyl-8-methyl-2-phenyl-2,3,4,5-tetrahydro-5H-pyridazino[4,5-b][1,5] thiazepin-9(8H)-one (5) was prepared by an intramolecular S-alkylation reaction, whereas the thiazepine ring of sulfone analogue 21, and that of the novel tricyclic pyrrolidino fused ring system 22 was elaborated by an intramolecular C-alkylation reaction. Unexpected formation of bicyclic pyrido- and thiazine fused pyridazine systems are also discussed.