6330-37-6

Usage

InChI:InChI=1/C7H11NO3/c1-3-11-6(9)4-7(2,10)5-8/h10H,3-4H2,1-2H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 141-97-9 ethyl acetoacetate 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 151-50-8 potassium cyanide 
• 124-63-0 methanesulfonyl chloride 
• 7677-24-9 trimethylsilyl cyanide 
• 136370-79-1 ethyl 3-trimethylsilanyloxy-3-cyanobutanoate 
• 143-33-9 sodium cyanide 

Downstream Products

• 53598-98-4 4-Hydroxy-4-methyl-2-pyrrolidon 
• 19735-89-8 3-methyl-1-phenylpyrazolin-5(4H)-one 
• 40595-04-8 (Z)-ethyl 3-cyanobut-2-enoate 
• 6330-35-4 (E)-ethyl 3-cyanobut-2-enoate 
• 74-90-8 hydrogen cyanide 
• 141-97-9 ethyl acetoacetate 
• 3120-04-5 3-methyl-1-phenylpyrrole-2,5-dione 

Relevant academic research and scientific papers

Catalytic Transfer Hydration of Cyanohydrins to α-Hydroxyamides

We report the palladium(II)-catalyzed transfer hydration of cyanohydrins to α-hydroxyamides by using carboxamides as water donors. This method enables selective hydration of various aldehyde- and ketone-derived cyanohydrins to afford α-mono- and α,α-disubstituted-α-hydroxyamides, respectively, under mild conditions (50 °C, 10 min). The direct conversion of fenofibrate, a drug bearing a benzophenone moiety, into a functionalized α,α-diaryl-α-hydroxyamide was achieved by means of a hydrocyanation-transfer hydration sequence. Preliminary kinetic studies and the synthesis of a site-specifically 18O-labeled α-hydroxyamide demonstrated the carbonyl oxygen transfer from the carboxamide reagent into the α-hydroxyamide product.

Rationalisation of the stereochemical outcome of ene-reductase-mediated bioreduction of α,β-difunctionalised alkenes

The OYE1-3-mediated reductions of some α,β-difunctionalised alkenes, showing on the double bond a nitrile and ester group, are submitted to a careful stereochemical analysis, in order to identify which of the two electron-withdrawing groups (EWGs) is resp

A single-step, mild, neutral, catalyst-free method for cyanohydrin synthesis

A wide variety of carbonyl compounds can be transformed to their corresponding cyanohydrins in a single step using a dimethyl sulfoxide (DMSO)-water system in excellent yields (75-94%). The major advantages of this system are that the reaction conditions are mild and neutral; the reaction proceeds without catalyst and gives the corresponding cyanohydrins in short time (15-120 min).

The CSIC [carbanion mediated sulfonate (sulfonamido) intramolecular cyclization] reaction: Scope and limitations

The CSIC (Carbanion-mediated Sulfonate-Sulfonamide-Intramolecular Cyclization) reaction has been extended to new carbonyl containing substrates, showing the scope and limitations of this process. Suitable derivatives of ketones (e.g acetophenone (1)), β-keto esters (e.g ethyl acetoacetate (4)), γ-keto esters (e.g ethyl 2-oxocyclohexaneacetate (5) and ethyl levulinate (6)) proved reluctant to undergo this protocol. Cyclopropyl methyl ketone (2) gave the heterocycle (3), only in the 'sulfonamide' synthetic sequence of the CSIC reaction. Cyclic azaketones (e.g tropinone (7)) fated also, but 4-piperidones (9, 10) afforded the novel 3,8- disubstituted 4-amino-8-aza-1-oxa-2-thiaspiro[4.5]dec-3-ene 2,2-dioxide (12, 15a-c) and 8-substituted 4-amino-1,8-diaza-2-thiaspiro[4.5]dec-3-ene 2,2- dioxide (18a, 18b, 21a, 21b) ring systems; the former compounds are the first examples of such ring systems substituted at the 3-position, whereas the latter represent the first ever representatives of spiro fused systems containing the 4-amino-2,3-dihydroisothiazole 1,1-dioxide moiety. Base promoted (NaH or DBU) cyclization of precursors 11b, 14a-c, 17b, 17c and 20 give the final adducts in good overall yield. Finally, we were unsuccessful with some conveniently functionalized anthranilonitrile derivatives (8a-d), in an attempt to extend the CSIC reaction to β-aminonitriles. As a result of these studies the substrate dependent reactivity in the CSIC reaction has been analyzed in depth and some restrictions and limitations have been observed and discussed.