30388-46-6

Upstream product

• 67-56-1 methanol 
• 1616794-66-1 4,6-O-benzylidene-2-chloro-4-nitrophenyl-β-maltotriosyl-α-(1,6)-maltotrioside 
• 619-08-9 2-chloro-4-nitrophenol 
• 55027-13-9 2-chloro-4-nitrophenyl methanesulfonate 
• 260967-21-3 2-chloro-4-nitrophenyl phenylacetate 
• 138554-69-5 Phosphoric acid 2-chloro-4-nitro-phenyl ester diphenyl ester 
• 18938-17-5 4-formylphenoxide ion 
• 261172-44-5 4-acetylphenoxide 
• 3229-70-7 phenolate 
• 18855-84-0 2-chloro-4-nitrophenyl acetate 
• 14609-76-8 4-cyanophenolate 
• 18938-14-2 3-chlorophenoxide 
• 288-32-4 1H-imidazole 
• 106644-72-8 Phosphoric acid 2-chloro-4-nitro-phenyl ester diethyl ester 

Relevant academic research and scientific papers

Ketene-forming elimination reactions from aryl phenylacetates promoted by R2NH in MeCN: Effects of base-solvent and β-phenyl group

Elimination reactions of C6H5C(R)HCO 2C6H3-2-X-4-NO2 [R = H (1), Ph (2), X = H (a), Cl (b), NO2 (c)] promoted by R2NH in MeCN have been studied kinetically. The reactions are second-order and exhibit Broensted β = 0.46-0.89 and |β1g| = 0.37-0.76 and an E2 mechanism is evident. When the base-solvent was changed from R 2NH/R2NH2+-70 mol% MeCN(aq) to R2NH-MeCN, β and |β1g| values remained nearly the same within experimental error. For eliminations from 1 and 2, β and |β1g| values were nearly identical, although the rate was retarded by the β-Ph group. Noteworthy is the relative insensitivity of the ketene-forming transition state to the base-solvent and β-R group variation. Copyright

Elimination Reactions of Aryl Furylacetates Promoted by R2NH in MeCN: Effects of Base Solvent and β-Aryl Group on the Ketene-forming Transition State

Ketene-forming elimination from C4H3(O)CH2C(O)OC6H3-2-X-4-NO2 (1) promoted by R2NH in MeCN has been studied. The reactions produced elimination products and exhibited second-orde

Structure-activity relationship of highly potent galactonoamidine inhibitors toward β-galactosidase (Aspergillus oryzae)

A small library of 22 N-substituted galactonoamidines was synthesized, and their structure-activity relationship for inhibition of the hydrolytic activity of β-galactosidase (Aspergillus oryzae) was evaluated. A fast screening assay in 96-well plate forma

Colourimetric and fluorometric substrates for measurement of pullulanase activity

Specific and highly sensitive colourimetric and fluorometric substrate mixtures have been prepared for the measurement of pullulanase and limit-dextrinase activity and assays employing these substrates have been developed. These mixtures comprise thermostable α- and β-glucosidases and either 4,6-O-benzylidene-2-chloro-4-nitrophenyl-β-maltotriosyl (1-6) α-maltotrioside (BzCNPG3G3, 1) as a colourimetric substrate or 4,6-O-benzylidene-4-methylumbelliferyl-β-maltotriosyl (1-6) α-maltotrioside (BzMUG3G3, 2) as a fluorometric substrate. Hydrolysis of substrates 1 and 2 by exo-acting enzymes such as amyloglucosidase, β-amylase and α-glucosidase is prevented by the presence of the 4,6-O-benzylidene group on the non-reducing end d-glucosyl residue. The substrates are not hydrolysed by any α-amylases studied, (including those from Aspergillus niger and porcine pancreas) and are resistant to hydrolysis by Pseudomonas sp. isoamylase. On hydrolysis by pullulanase, the 2-chloro-4-nitrophenyl-β-maltotrioside (3) or 4-methylumbelliferyl-β- maltotrioside (4) liberated is immediately hydrolysed to d-glucose and 2-chloro-4-nitrophenol or 4-methylumbelliferone. The reaction is terminated by the addition of a weak alkaline solution leading to the formation of phenolate ions in solution whose concentration can be determined using either spectrophotometric or fluorometric analysis. The assay procedure is simple to use, specific, accurate, robust and readily adapted to automation.

Structure and mechanism of PhnP, a phosphodiesterase of the carbon-phosphorus lyase pathway

PhnP is a phosphodiesterase that plays an important role within the bacterial carbon-phosphorus lyase (CP-lyase) pathway by recycling a "dead-end" intermediate, 5-phospho-α-d-ribosyl 1,2-cyclic phosphate, that is formed during organophosphonate catabolism

Study on the transesterification of methyl aryl phosphorothioates in methanol promoted by Cd(II), Mn(II), and a synthetic Pd(II) complex

Methanol solutions containing Cd(II), Mn(II), and a palladacycle, (dimethanol bis(N,N-dimethylbenzylamine-2C,N)palladium(II) (3), are shown to promote the methanolytic transesterification of O-methyl O-4-nitrophenyl phosphorothioate (2b) at 25 °C with impressive rate accelerations of 10 6-1011 over the background methoxide promoted reaction. A detailed mechanistic investigation of the methanolytic cleavage of 2a-d having various leaving group aryl substitutions, and particularly the 4-nitrophenyl derivative (2b), catalyzed by Pd-complex 3 is presented. Plots of k obs versus palladacycle [3] demonstrate strong saturation binding to form 2b:3. Numerical fits of the kinetic data to a universal binding equation provide binding constants, Kb, and first order catalytic rate constants for the methanolysis reaction of the 2b:3 complex (kcat) which, when corrected for buffer effects, give corrected (kcat corr) rate constants. A sigmoidal shaped plot of log(k catcorr) versus sspH (in methanol) for the cleavage of 2b displays a broad sspH independent region from 5.6 ≥ sspH ≥ ～10 with a k minimum = (1.45 ± 0.24) × 10-2 s-1 and a [lyoxide] dependent wing plateauing above a kinetically determined sspKa of 12.71 ± 0.17 to give a k maximum = 7.1 ± 1.7 s-1. Bronsted plots were constructed for reaction of 2a-d at sspH 8.7 and 14.1, corresponding to reaction in the midpoints of the low and high s spH plateaus. The Bronsted coefficients (βLG) are computed as -0.01 ± 0.03 and -0.86 ± 0.004 at low and high sspH, respectively. In the low sspH plateau, and under conditions of saturating 3, a solvent deuterium kinetic isotope effect of kH/kD = 1.17 ± 0.08 is observed; activation parameters (ΔHPd? = 14.0 ± 0.6 kcal/mol and ΔSPd?= -20 ± 2 cal/mol?K) were obtained for the 3-catalyzed cleavage reaction of 2b. Possible mechanisms are discussed for the reactions catalyzed by 3 at low and high sspH. This catalytic system is shown to promote the methanolytic cleavage of O,O-dimethyl phosphorothioate in CD3OD, producing (CD3O)2P=O(S-) with a half time for reaction of 34 min.

Pitfalls in assessing the α-effect: Reactions of substituted phenyl methanesulfonates with HOO-, OH-, and substituted phenoxides in H2O

Toward resolving the current controversy regarding the validity of the α-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-1l with HOO-, OH-, and Z-substituted phenoxides in the gas phase versus solu

Ketene-forming elimination reactions from aryl thienylacetates promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq). Effect of the β-aryl group

(Chemical Equation Presented) Ketene-forming eliminations from ArCH 2CO2C6H3-2-X-4-NO2 (Ar = thienyl, 1) promoted by R2NH/ R2NH2+ in 70 mol % MeCN(aq) have

Ketene-forming eliminations from aryl phenylacetates promoted by R2NH/R2NH2+ in aqueous MeCN. Mechanistic borderline between E2 and E1cb

Elimination reactions of 2-X-4-NO2C6H3CH2C(O) OC6H3-2-Y-4-NO2 [X = H (1), NO2 (2)] promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq) have been studied kinetically. The base-promoted eliminations from 1 proceeded by the E2 mechanism when Y = Cl, CF3, and NO2. The mechanism changed to the competing E2 and E1cb mechanisms by the poorer leaving groups (Y = H, OMe) and to the E1cb extreme by the strongly electron-withdrawing β-aryl group (2, X = NO2). The values of β = 0.14 and |β1g| = 0.10-0.21 calculated for elimination from 1 (Y = NO2) indicate a reactant-like transition state with small extents of proton transfer and Cα-OAr bond cleavage. The extent of proton transfer increased with a poorer leaving group, and the degree of leaving group bond cleavage increased with a weaker base. Also, the changes in the k1 and k-1/k2 values with the reactant structure variation are consistent with the E1cb mechanism. From these results, a plausible pathway of the change of the mechanism from E2 to the E1cb extreme is proposed.