14368-31-1

Upstream product

• 98-86-2 acetophenone 
• 590-17-0 cyanomethyl bromide 
• 38046-39-8 cyanomethylzinc bromide 
• 75-05-8 acetonitrile 
• 107-14-2 chloroacetonitrile 
• 111873-50-8 dibutyl(cyanomethyl)telluronium chloride 
• 138123-05-4 C₂H₂CeCl₂N 
• 97364-09-5 NCCH₂Ti(OCH(CH₃)2)3 
• 624-75-9 iodoacetonitrile 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 1446698-46-9 (dimethylsilyl)acetonitrile 
• 127-66-2 2-Phenyl-3-butyn-2-ol 

Downstream Products

• 104294-60-2 4-amino-2-phenylbutan-2-ol 
• 1114064-50-4 3-(4-bromobenzyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one 
• 1114064-48-0 6-methyl-6-phenyl-1,3-oxazinan-2-one 
• 3759-31-7 3-hydroxy-3-phenylbutanoic acid 

Relevant academic research and scientific papers

Conversion of 3,3,3-Trisubstituted Prop-1-ynes with tert-Butylhydrazine into 3,3,3-Trisubstituted Propionitriles Catalyzed by TpRh(C2H4)2/P(2-furyl)3

The combination of TpRh(C2H4)2 (Tp = tris(pyrazol-1-yl)borate) and P(2-furyl)3 catalyzes the reaction of tertiary alkyl-substituted alkynes with tert-butylhydrazine, leading to the formation of 3,3,3-trisubstituted propionitrile derivatives. This reaction system is applicable to 1,1-disubstituted propargyl alcohols and amines to afford the corresponding β-cyanohydrins and β-amino nitriles, respectively. The catalytic cycle involves the formation of a vinylidenerhodium complex as a key intermediate.

Zinc-mediated addition of bromoacetonitrile to carbonyl compounds under solvent-free conditions

Zinc mediated addition reaction of bromoacetonitrile with aryl aldehydes and ketones produces β-hydroxynitriles under solvent-free conditions. The valuable feature of the methodology are solvent-free and catalyst-free conditions and short reaction times (5 min).

Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones

α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR 3R4CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2/su

Metal or ammonium alginates as Lewis base catalysts for the 1,2-addition of silyl nucleophiles to carbonyl compounds

Several metal (Na+, Ca2+) or ammonium (n-Bu 4N+) derivatives of alginic acid, an abundant bio-polymer obtained from the cell walls of brown algae, were synthesized. Their potential to act as organocatalysts to catalyze the 1,2-addition of various silyl derivatives to carbonyl compounds was evaluated for the first time. Ammonium alginate 1h is able to promote the reaction in modest to good isolated yields (up to 98%) affording access to a large range of substrates (β-cyano alcohols or ester, β-substituted methylacrylate or acrylonitrile, and cyanohydrin) by using only 5 mol % of catalyst.

Structure-based design and synthesis of 1,3-oxazinan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase type 1

Structure based design led directly to 1,3-oxazinan-2-one 9a with an IC50 of 42 nM against 11β-HSD1 in vitro. Optimization of 9a for improved in vitro enzymatic and cellular potency afforded 25f with IC 50 values of 0.8 nM for the enzyme and 2.5 nM in adipocytes. In addition, 25f has 94% oral bioavailability in rat and >1000× selectivity over 11β-HSD2. In mice, 25f was distributed to the target tissues, liver, and adipose, and in cynomolgus monkeys a 10 mg/kg oral dose reduced cortisol production by 85% following a cortisone challenge.

Reaction of the electrogenerated cyanomethyl anion with carbonyl compounds: A clean and safe synthesis of β-hydroxynitriles

The electrogenerated cyanomethyl anion reacts with carbonyl compounds to yield the corresponding β-hydroxymtriles in moderate to high yields. The reported methodology is very clean and safe, avoiding the use of any classical base or catalyst.

CYCLIC INHIBITORS OF 11β-HYDROXYSTERIOD DEHYDROGENASE 1

This invention relates to novel compounds of the Formula (I), (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih); (Ii); (Ij), (Ik), (II) pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11 β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of cortisol in a cell or the inhibition of the conversion of cortisone to cortisol in a cell.

Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine

A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.

Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl)acetonitrile

Catalytic cyanomethylation of various carbonyl compounds with (trimethylsilyl)acetonitrile (TMSCH2CN) in the presence of Lewis bases such as cesium or lithium acetate proceeded smoothly to afford the corresponding cyanomethylated adducts in good yields. Copyright

Addition of α-halo-substituted carbonitriles to and aldehydesketones in the presence of iron pentacarbonyl

Halo-substituted carbonitriles in the presence of iron pentacarbonyl react with aldehydes and ketones by Reformatsky reaction type. In contract to halo-substituted esters the nitriles are considerably more reactive toward ketones than aldehydes. At the same time the structure and yield of products obtained from both nitriles and esters are strongly and similarly affected by the character of the para-substituents in the benzaldehyde.