779-80-6

Basic information

• Product Name: Benzoic acid, 3-nitro-, 2-propenyl ester
• CAS NO: 779-80-6
• Molecular Formula: C10H9NO4
• Molecular Weight: 207.186
• Mol File: 779-80-6.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3-nitro-, 2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-nitro-, 2-propenyl ester(779-80-6)
• EPA Substance Registry System: Benzoic acid, 3-nitro-, 2-propenyl ester(779-80-6)

Safety Data

• Hazardous Substances Data: 779-80-6(Hazardous Substances Data)

Upstream product

• 106-95-6 allyl bromide 
• 121-92-6 3-nitrobenzoic acid 
• 99-61-6 3-nitro-benzaldehyde 
• 107-18-6 allyl alcohol 
• 584-08-7 potassium carbonate 
• 121-90-4 m-nitrobenzoic acid chloride 

Downstream Products

• 56768-05-9 3-aminobenzoic acid allyl ester 
• 1384266-38-9 (Z)-prop-1-enyl 3-nitrobenzoate 
• 1384266-37-8 (E)-prop-1-enyl 3-nitrobenzoate 
• 121-92-6 3-nitrobenzoic acid 
• 1372715-51-9 1-methoxy-1-oxo-2-phenylpent-4-en-2-yl 3-nitrobenzoate 
• 188578-71-4 (2S,4R)-2-(3-Allyloxycarbonyl-phenylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid allyl ester 
• 188578-72-5 (1S,4S)-5-(3-Allyloxycarbonyl-phenyl)-6-oxo-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid allyl ester 
• 188578-73-6 2-(3-Carboxyphenyl)-2,5-diazabicyclo[2.2.1]heptan-3-one 

Relevant articles and documents

[Pd(μ-Br)(PtBu3)]2 as a highly active isomerization catalyst: Synthesis of enol esters from allylic esters

The dimeric Pd(I)-complex [Pd(μ-Br)(PtBu3)] 2 was found to be highly active for catalyzing double-bond migration in various substrates such as unsaturated ethers, alcohols, amides, and arenes, under mild conditions. It efficiently mediates the conversion of allylic esters into enol esters, rather than inserting into the allylic C-O bond. The broad applicability of this reaction was demonstrated with the synthesis of 22 functionalized enol esters.

Palladium-catalyzed divergent reactions of α-diazocarbonyl compounds with allylic esters: Construction of quaternary carbon centers

Take two: α-Diazocarbonyl compounds display a diverse pattern of reactivity upon palladium-catalyzed reaction with esters. Esters bearing an alkynyl group on the carbonyl carbon atom lead to two different C-C bonds at the same carbon atom in a single operation through decarboxylation and migratory insertion, whereas aromatic and benzylic acid derivatives afford aromatic and benzylic esters bearing an O-substituted quaternary carbon center. Copyright

A facile direct conversion of aldehydes to esters and amides using acetone cyanohydrin

Aromatic aldehydes with electron-withdrawing groups undergo rapid reactions with a variety of alcohols and secondary amines to afford the corresponding esters and amides, respectively, in high yields, when treated with NaCN or acetone cyanohydrin and base under ambient reaction conditions. In case of α,β-unsaturated aldehydes, simultaneous reduction of the CC bond along with esterification occurred to produce the saturated esters in high yields.

An unexpected Mitsunobu reaction. A direct route to the 2,5-diazabicyclo[2.2.1]heptan-3-one skeleton as a γ-lactam mimic of β-lactam antibiotics

Treatment of anilides of N-protected (2S,4R)-4-hydroxyproline, e.g. 1, with thioacetic acid under Mitsunobu conditions gives, unexpectedly, 2,5-diazabicyclo[2.2.1]heptan-3-ones, e.g. 2, the products of intramolecular cyclisation. However, the less acidic N-benzylamides of these proline derivatives, e.g. 7, are not sufficiently acidic and the hydrazido anion generated in the Mitsunobu reaction displaces the activated hydroxy group in an intermolecular reaction to give 8. The bicyclic γ-lactams are potential analogues of the β-lactam antibiotics and suitable derivatives 9, 10,11 and 12 are found to be competitive inhibitors of class A and C β-lactamases, with Ki as low as 70 μM.

Antibiotic penem compounds

The present invention provides a compound of the formula (I) STR1 wherein: R1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R2 is hydrogen or C1-4 alkyl; Z is carboxy, sufonic acid, tetrazol-5-yl or C 1-4 alkylsulfonylcarbamoyl (--CONHSO2 C1-4 alkyl); A is a phenyl or thienyl ring; and A is optionally further substituted by one or two substituents or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.

Antibiotic compounds

The present invention relates to carbapenems and provides a compound of the formula (I): STR1 or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof wherein: R1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R2 is hydrogen or C1-4 alkyl; R3 is hydrogen or C1-4 alkyl; R4 and R5 are the same or different and are selected from hydrogen, halo, cyano, C1-4 alkyl, nitro, hydroxy, carboxy, C1-4 alkoxy, C1-4 alkoxycarbonyl, aminosulphonyl, C1-4 alkylaminosulphonyl, di-C1-4 alkylaminosulphonyl, carbamoyl, C1-4 alkylcarbamoyl, di-C1-4 alkylcarbamoyl, trifluoromethyl, sulphonic acid, amino, C1-4 alkylamino, di-C1-4 alkylamino, C1-4 alkanoylamino, C1-4 alkanoyl(N-C1-4 alkyl)amino, C1-4 alkanesulphonamido and C1-4 alkylS(O)n -- wherein n is zero, one or two: with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the --NR2 --. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.

Mild, one-pot conversion of carboxylic acids into esters using phase transfer catalysis

One-pot conversion of carboxylic acids into esters under the influence of phase transfer catalysis is reported.The method is shown to work satisfactorily for optically active acids having epimerisable α-hydrogen.