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CAS No. : | 600-14-6 | MDL No. : | MFCD00009313 |
Formula : | C5H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TZMFJUDUGYTVRY-UHFFFAOYSA-N |
M.W : | 100.12 | Pubchem ID : | 11747 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 26.55 |
TPSA : | 34.14 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.87 cm/s |
Log Po/w (iLOGP) : | 1.47 |
Log Po/w (XLOGP3) : | 0.06 |
Log Po/w (WLOGP) : | 0.55 |
Log Po/w (MLOGP) : | -0.02 |
Log Po/w (SILICOS-IT) : | 0.68 |
Consensus Log Po/w : | 0.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.37 |
Solubility : | 43.1 mg/ml ; 0.43 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.33 |
Solubility : | 46.8 mg/ml ; 0.467 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.88 |
Solubility : | 13.3 mg/ml ; 0.132 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P305+P351+P338 | UN#: | 1224 |
Hazard Statements: | H225-H315-H319 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.5% | Stage #1: at -5 - 70℃; for 7 h; Stage #2: With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 30 - 70℃; for 5 h; |
At -5 to 3°C,The above-prepared 2,3-pentanedione, ethylenediamine and anhydrous ethanol were mixed and stirred in a three-necked flask and reacted for 7 hours.After the reaction is over, the system is warmed to room temperature.Stirring at room temperature for 3h,Then warm up to 65-70 °C, reflux 4h,After cooling is completed, cool rapidly to 30-40°C.Then add xylene to the three-necked flask,Potassium hydroxide catalysts,After the addition is complete, continue to heat up to 65-70°C,Reflux 5h,After the reaction is completed, it is cooled to room temperature.With suction filtration, the filtrate is distilled at atmospheric pressure.The distilled concentrate was diluted with saturated saline solution.extraction,Combine the organic phase,Dry with anhydrous copper sulfate, overfilter,Atmospheric pressure steamed extractant,Fractions from 55-60°C/1.33 KMa were collected to give 2-ethyl-3-methylpyrazine;The product yield is over 93.5percent;among them,The mass ratio of 2,3-pentanedione, ethylenediamine and anhydrous ethanol is 1:1.1:70;The mass ratio of 2,3-pentanedione, potassium hydroxide, catalyst and xylene was 1:0.8:2.8:1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.5% | With aluminum oxide; potassium fluoride; at 200℃; | 75 g of a lactic acid solution (content: 90%) and 5 g of the solid base catalyst prepared above were mixed, and the reaction mixture was slowly heated. When the reaction temperature reached 200 C, the lactic acid was subjected to condensation dehydration and decarboxylation to form 2,3-pentanedione. At the same time, the produced 2,3-pentanedione and water were vaporized from the reaction mixture system, and after cooling through a condenser, 2,3-pentanedione and a water fraction were collected. As the reaction progresses, the kettle temperature rises slowly, and the distillation rate becomes slow until no significant fraction is distilled off, heating is stopped, and the reaction is terminated. The collected 2,3-pentanedione and water fraction were allowed to stand for separation; the lower aqueous phase was extracted with ethyl acetate, combined with the upper 2,3-pentanedione, the organic phase was fractionated, the solvent was recovered, and the rectification was carried out to obtain 28.15 g. 2,3-pentanedione, the yield was 81.5%. 2,3-pentanedione was detected by gas chromatography and the content was over 99%. |
With caesium supported on porous carrier; at 260℃;Sealed tube;Catalytic behavior; | 0.3 g of the above-prepared catalyst is placed in a quartz tube,The length of the catalyst in the quartz tube is 30mm.The ends of the catalyst are sealed with quartz wool.Lactic acid aqueous solution with nitrogen carried through the quartz tube containing the catalyst,And vaporize on the surface of quartz wool,The steam feed then passes over the catalyst surface,The reaction temperature is 260C.The lactic acid concentration is 10% by weight.The feed rate is 0.3 mL/h and the carrier gas flow rate is 1 mL/min.2,3-pentanedione was obtained;The selectivity of lactic acid is 98.5% or more; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.3% | With hydrogen In isopropyl alcohol at 100℃; for 1h; Autoclave; Sealed tube; | |
83% | With hydrogen In isopropyl alcohol at 85℃; for 4.5h; Autoclave; | 1.2-3.2 (2) Hydrogenation of pentanedione to prepare pentanediol: After calcining the Al2O3 carrier at 550°C for 4h, weigh 3.0g into a beaker, add 3ml of lanthanum nitrate solution, control the loading of lanthanum nitrate to 20%, let stand overnight, and dry at 120°C for 8h. The resulting product is calcined at 500°C 5h; then impregnate with 3ml of chloroplatinic acid solution (concentration of 10mg/ml), stir for 10min, stand overnight, dry in an oven at 120 for 8h, then calcine at 550 for 5h, and then treat it in a hydrogen atmosphere at 400 for 4h to obtain Pt/La/Al2O3 hydrogenation catalyst. Weigh 1.0g of hydrogenation catalyst in a stainless steel autoclave with tetrafluoroethylene lining, add 8.5g of pentanedione and dilute to 50ml with isopropanol, fill it with H2 replacement 3 times, and then press 7MPaH2, set the reaction The temperature is 85°C and the reaction time is 4.5h. The yield of pentanediol was 83%, and the conversion of pentanedione was 94%. |
83% | With hydrogen In isopropyl alcohol at 85℃; for 4.5h; Autoclave; | 4.2; 5.2 (2) Hydrogenation of pentanedione to prepare pentanediol: After calcining the Al2O3 carrier at 550°C for 4h, weigh 3.0g into a beaker, add 3ml of lanthanum nitrate solution, control the loading of lanthanum nitrate to 20%, let stand overnight, and dry at 120°C for 8h. The resulting product is calcined at 500°C 5h; then impregnate with 3ml of chloroplatinic acid solution (concentration of 10mg/ml), stir for 10min, stand overnight, dry in an oven at 120 for 8h, then calcine at 550 for 5h, and then treat it in a hydrogen atmosphere at 400 for 4h to obtain Pt/La/Al2O3 hydrogenation catalyst. Weigh 1.0g of hydrogenation catalyst in a stainless steel autoclave with tetrafluoroethylene lining, add 8.5g of pentanedione and dilute to 50ml with isopropanol, fill it with H2 replacement 3 times, and then press 7MPaH2, set the reaction The temperature is 85°C and the reaction time is 4.5h. The yield of pentanediol was 83%, and the conversion of pentanedione was 94%. |
bei der vollstaendigen Reduktion durch gaerende Hefe; Trennung der Isomeren durch fraktionierten Krystallisation der Bis-phenylurethane aus Aethanol; dextrorotatory form; | ||
bei der vollstaendigen Reduktion durch gaerende Hefe; Trennung der Isomeren durch fraktionierten Krystallisation der Bis-phenylurethane aus Aethanol; (-)-pentanediol-(2,3); | ||
With 2,3,4,5,6-pentahydroxy-hexanal; Bacillus subtilis glucose dehydrogenase; Saccharomyces cerevisiae dehydrogenase Gre2p; NADPH; magnesium chloride at 30℃; aq. buffer; Enzymatic reaction; | ||
Stage #1: 2,3-Pentanedione With sodium tetrahydroborate In methanol at 20℃; for 3h; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 7 fbetabetaft J B) Synthesis of 2-Ethyi-3-ruethylqtoosaHne. as ouilhied in the synthetic scheme given below. TheHPLC trace is show in Figure 4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide; bromine; acetic acid; In chloroform; at 50℃; for 3h; | 4-bromo<strong>[600-14-6]pentane-2,3-dione</strong>.[0352] To a solution of <strong>[600-14-6]pentane-2,3-dione</strong> (1.00 g, 9.99 mmol) in chloroform (30 mL) was added bromine (1.60 g, 10.01 mmol) and hydrogen bromide in acetic acid (33 wt ; 3 drops). The resulting solution was stirred for 3 h at 50 C. The resulting solution was concentrated to afford 4-bromopentane- 2,3-dione as a solid (1.79 g). The crude product was used in next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium bromate; hydrogen bromide; In chloroform; at 25 - 35℃; for 11.5h; | In a 500 mL reaction vessel, add <strong>[600-14-6]2,3-pentanedione</strong> 10 g, sodium bromate 12.08 g, chloroform 100 ml, slowly at 25CA solution of hydrogen bromide (81g, 40wt%) was added dropwise. The addition was complete for 2.5 h, slowly warmed to 35C, and stirred at this temperature for 3 h.After standing and GC monitoring, the reaction was complete after 6 h, and the liquid was separated. After the organic phase was desolved, the 87 C./5 mm fraction was collected by vacuum distillation to obtain the product 1,4-dibromo-<strong>[600-14-6]2,3-pentanedione</strong> (yield 92%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
bioreduction of other diketones by baker's yeast; selectivity; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen sulfide In ethanol Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | General procedure: To a stirred mixture of lithium carbonate (9 g. 176 mmol) and 1 mL of <strong>[600-14-6]2,3-pentanedione</strong> (10 mmol) in dry Toluene under Nitrogen atmosphere, 2 g of triethylamine (2.8 ml, 20 mmol) were added, then the reaction was kept away from light and stirred for 30 minutes. A solution of the corresponding isocianate (15 mmol) in 2 mL of toluene or dioxane (4-chlorophenylisocyanate) was add dropwise for 10 minutes. After 20 hours of reaction the mixture is filter over celite, washing the filtrate with CH2Cl2, and the residue concentrated and purified by column chromatography using 10% triethylamine silica. (Z)-3-(4-chlorophenyl)-5-ethylidene-4-methyleneoxazolidin-2-one (3a). White solid. Yield 40%. m. p. 79-80 C. 1H NMR (300 MHz, CDCl3) delta (ppm): 7.47 (d, J = 8.7 Hz, 2H), 7.30 (d, J = 8.6 Hz, 2H), 5.43 (q, J = 7.3 Hz, 1H), 4.60 (d, J = 3.1 Hz, 1H), 4.18 (d, J = 3.1 Hz, 1H), 1.86 (d, J = 7.3 Hz, 3H).13C NMR (75.4 MHz, CDCl3) delta (ppm): 152.7(C=O), 143.1 (C), 139.0 (C), 134.6 (C), 131.9 (C), 130.1 (C), 128.5 (C), 99.8 (C), 81.9 (C), 77.4(C), 10.6 (Me). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | General procedure: To a stirred mixture of lithium carbonate (9 g. 176 mmol) and 1 mL of <strong>[600-14-6]2,3-pentanedione</strong> (10 mmol) in dry Toluene under Nitrogen atmosphere, 2 g of triethylamine (2.8 ml, 20 mmol) were added, then the reaction was kept away from light and stirred for 30 minutes. A solution of the corresponding isocianate (15 mmol) in 2 mL of toluene or dioxane (4-chlorophenylisocyanate) was add dropwise for 10 minutes. After 20 hours of reaction the mixture is filter over celite, washing the filtrate with CH2Cl2, and the residue concentrated and purified by column chromatography using 10% triethylamine silica. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ozone for 0.0015h; reaction in gas phase; mass spectrum of ozone and title compound; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | [3-Chloro-5-(5-ethyl-4-methyl-1 H-imidazol-2-yl)-pyridin-2-yl]-(4-chloro-phenyl)-amine A mixture of 5-chloro-6-(4-chloro-phenylamino)-pyridine-3-carbaldehyde (1.5 g, 5.62 mmol), <strong>[600-14-6]2,3-pentanedione</strong> (447 mul, 4.15 mmol) and NH4OAc (1.62 g, 20.8 mmol) in AcOH (15 ml) were heated to 180C for 2 h in a microwave oven. The mixture was then poured onto aq. NH4OH solution and extracted with EtOAc. The combined org. phases were then dried and evaporated. Purification by flash chromatography (Hex/EtOAc 100:0 to 30:70) provided [3- chloro-5-(5-ethyl-4-methyl-1 H-imidazol-2-yl)-pyridin-2-yl]-(4-chloro-phenyl)-amine (500 mg, 26%). UPLC (5-100% CH3CN): RT = 1.213 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With ozone; In methanol; | EXAMPLE 3 Preparation of pentane-2,3-dione Starting from II, R1=methyl, R2=ethyl, R3=dimethylamino, R4=H A solution of 78% of 1-(dimethylamino)-2-methylpent-1-en-3-one (3.75 g; 0.021 mol) in methanol (35 ml) was cooled to -78 C. and ozone was introduced at a rate of 3.4 g/h over 1 h. Excess ozone was driven out with nitrogen. The reaction mixture was treated with dimethyl sulphide (1.51 g; 0.024 mol) and slowly heated to 25 C. The yield of pentane-2,3-dione was determined as 19% in the reaction mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In water | 2 EXAMPLE 2 EXAMPLE 2 Potassium lactate preparation Potassium hydroxide as solid pellets (85% KOH) in the amount of 22.086 g was dissolved into 23.344 g water. To this solution was added 34.196 g 88% lactic acid solution to give 79.592 g of a potassium lactate solution containing 53.80 weight percent potassium lactate and 46.20% water. Condensed-phase formation of 2,3-pentanedione with potassium lactate as catalyst |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: fipronilβ-cyclodextrin With pectin In water at 4.5 - 48℃; for 0.5h; Stage #2: 2,3-Pentanedione In water at 4.5℃; for 44h; | 4 A molar excess of acetyl propionyl was added to a dry blend of β-cyclodextrin and 2 wt % pectin in water, following the method set forth in Example 1. The percent retention of acetyl propionyl in the cyclodextrin inclusion complex was 9.27 wt %. The mixture can be useful in top-noting diacetyl-free butter systems. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7%Spectr.; 74% | With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; triethylamine; In PEG400; at 20℃; | General procedure: Method B. To a vigorously stirred mixture of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride 2b (54 mg, 0.20 mmol), Et3N (140 muL, 1.00 mmol), and PEG400 (4 mL) alpha-diketone 1 (2.00 mmol) was added in one portion. The mixture was stirred at room temperature until TLC analysis revealed the disappearance of the starting alpha-diketone (12-24 h). The reaction medium was then diluted with Et2O (5 mL), vigorously stirred for 5 min, allowed to separate out and the ethereal solution was decanted. This process was repeated twice to obtain the crude alpha-hydroxyketone 3 in Et2O, whereas the mother liquor (PEG400-methylthiazolium 2b) was kept aside for further runs. The extraction solvent was then removed under a nitrogen stream and the residue containing the target alpha-hydroxyketone purified as described above. Product yields for Method B are reported in refPreviewPlaceHolderTable 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98%Chromat. | With [(S)-BINAP]PdBr2; hydrogen; In dichloromethane; at 120℃; under 41372.9 Torr; for 24h;Autoclave; | General procedure: From a Schlenk tube under nitrogen atmosphere, a solution of a-diketone (1mmol), aniline (1mmol), [(S)-BINAP]PdBr2] (0.025 mol), in CH2Cl2 (10 ml) was transferred to a 45 ml stainless steel Parr vessel and the vessel was pressurized with 800 psi of hydrogen gas. The reactor was placed in a preheated oil bath at 120 C with magnetic stirring over different periods of time (24, 48h). The reaction mixture was purified by column chromatography using hexane and methylene chloride as eluents and was analyzed by GC-MS. The formation of intermediates involved in the process was achieved by varying the reaction time (12, 24h), and these intermediates were purified by column chromatography with hexane and ethylacetate as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [(S)-BINAP]PdBr2; hydrogen; In dichloromethane; at 120℃; under 41372.9 Torr; for 12h;Autoclave; | General procedure: From a Schlenk tube under nitrogen atmosphere, a solution of a-diketone (1mmol), aniline (1mmol), [(S)-BINAP]PdBr2] (0.025 mol), in CH2Cl2 (10 ml) was transferred to a 45 ml stainless steel Parr vessel and the vessel was pressurized with 800 psi of hydrogen gas. The reactor was placed in a preheated oil bath at 120 C with magnetic stirring over different periods of time (24, 48h). The reaction mixture was purified by column chromatography using hexane and methylene chloride as eluents and was analyzed by GC-MS. The formation of intermediates involved in the process was achieved by varying the reaction time (12, 24h), and these intermediates were purified by column chromatography with hexane and ethylacetate as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Example 7Synthesis of 2-tert-butyl-4-methyl-5-ethyl-imidazole A mixture of 23.65 g (0.275 mol) of pivaldehyde, 77.1 g ( 1 .000 mol) of ammonium acetate, and 90.10 g (1.500 mol) of acetic acid was charged into 500 ml flask equipped with addition funnel. The mixture was heated to 90-95C and 25.0 g (0.25 mol) of 2,3- pentanedione was added from the addition funnel within ~ 20 minutes. The mixture was heated for 2 hours at 1 10C and cooled to room temperature (RT). The resulting product mixture was extracted with 300 ml of hexane to remove oxazole derivatives. The remaining fraction was neutralized with sodium bicarbonate solution. The product was extracted with 2x150 ml of diethyl ether. The combined ether layers were washed with 2 x 100 mL of water then 100 ml of saturated sodium chloride solution. 10g of anhydrous magnesium sulfate was added and stirred overnight. Filtration followed by removal of ether by vacuum yielded the crude product as a yellow solid. The material was purified by vacuum sublimation to yield 4.0 g of 2-tert-butyl-4-methyl-5-ethyl-imidazole (56 % yield).Mass spectrum: 166 mu (parent ion). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: A mixture of oxalaldehyde (1 mmol) 2,3-diaminomaleonitrile (1 mmol), sodium azide (3 mmol) in DMSO (2 mL) was stirred at 100 C for 6 h. After completion of the reaction confirmed by TLC (eluent: EtOAc/n-hexane, 1:1), the solvent was evaporated under reduced pressure. To the participate was added 20 mL of 2 N HCl with vigorous stirring causing the 2,3-di(1H-tetrazole-5-yl) pyrazine to precipitate. The precipitate was filtered and dried in a drying oven to furnish the 2,3-di(1H-tetrazole-5-yl) 5a as white powder (0.20 g, yield 93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 98%Chromat. | With recombinant aldo-keto reductase AKR5G (Ydl124p) from Saccharomyces cerevisiae; NADPH; In aq. phosphate buffer; at 25℃;pH 7;Enzymatic reaction; | Enzyme activities were determined spectrophotometrically by measuring the change of absorbance at 340 nm and 25 C, corresponding to the oxidation of NADPH (epsilon340 = 6220 M-1 cm-1). One unit of activity (U) corresponds to 1 mumol of NADP+ formed per min. The specific activities were measured in 33 mM sodium phosphate, pH 7.0, in the presence of 100 mM diacetyl and 0.2 mM NADPH. Kinetic constants were obtained with the non-linear regression (Michaelis-Menten Equation) program Grafit 5.0 (Erithacus Software Ltd, Horley, UK). The standard errors of the fits were less than 10% of the values. The concentration of enzymes (for calculation of kcat values) was determined by a commercial Bradford reagent, according to manufacturer?s instructions (Bio-Rad Laboratories Inc., USA) and using bovine serum albumin as standard. The chemical transformations of the diketones in alpha-hydroxy ketones and diols were carried out through overnight reactions prepared in 2-mL tubes from Sarstedt with continuous agitation at room temperature. The initial composition of the reactions was 50 mM diketone (diacetyl, 2,3-pentanodione, 2,3-hexanedione or 3,4-hexanedione), 1 mM NADPH in 33 mM sodium phosphate, pH 7.0, and an NADPH-regenerating system containing 100 mM glucose-6-phosphate and 3 U glucose-6-phosphate dehydrogenase. The reaction mixtures contained approximately 3 U of yeast AKR and 0.2 U of human enzymes (measured with 100 mM diacetyl and 0.2 mM NADPH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / ethanol; water / -5 °C / pH 8.5 2.1: hydrogen / acetic acid / 25 °C / 2250.23 Torr 2.2: 100 °C 3.1: acetic acid / 14 h / 50 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.2%Chromat. | With sodium hydroxide; In ethanol; water; at -5℃;pH 8.5; | <strong>[600-14-6]2,3-pentanedione</strong> and hydroxylamine hydrochloride were dissolved separately in water/EtOH (3/1; w/w %). Then the solution of hydroxylamine hydrochloride was added to the solution of <strong>[600-14-6]2,3-pentanedione</strong> at predetermined pH and low or room temperature. The pH-value of the reaction-mixture was adjusted with 1N NaOH. The final concentration of <strong>[600-14-6]2,3-pentanedione</strong> in the reaction-mixture was 3.5 w %. After the reaction, the solution was extracted with MTBE. [0109] The same procedure was repeated at various temperatures and pH values. The results are presented in Tables 1 and 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With calcium phosphate hydroxyapatite; ammonia; sodium hydroxide; In water; at 349.84℃; for 6h;Inert atmosphere; | General procedure: The typical catalytic conversions of lactic acid to acrylic acid werecarried in a fixed-bed continuous-flow reactor under atmosphericpressure. Before reaction, the pelletized catalysts (0.2-1.0 g) werepretreated at 773 K for 3 h in Ar flow and cooled to 623 K. 38 wt.% lacticacid aqueous solution (1.2 mL h-1) was introduced into the reactor by amicrosyringe pump with 40 mL min-1 of Ar gas. The products werecondensed in an ice-water trap. The collected liquid products were analyzedon a GC-FID (Shimadzu GC14B) with a Stabilwax-DA column.And, after the dilutions of the collected liquid products with distilledwater into 50 mL, they were analyzed using an HPLC (HITACHI LC-2000withUVdetector)with a Shodex KC811 column, and a total organiccarbon analyzer (TOC2000, Shimadzu). The gas product of acetaldehydewas determined by on-line GC-TCD (Shimadzu GC8A) with aGaskuropack 54. CO and CO2 were non-quantitatively analyzed by onlineGC-TCD. The lactic acid conversion and product yieldwere calculatedbased on the following equations: | |
With dipotassium hydrogenphosphate; for 3h; | In the first set of experiments, NaZSM-5 zeolite was modified by impregnating one of the five different potassium phosphate compounds as provided in Table 7 and each of the modified NaZSM-5 zeolites was tested for their efficiency in vapor phase dehydration reaction. The vapor phase dehydration reaction using lactic acid as a reactant was carried out using the following experimental parameters: Gas flow rate: 55cc/mm; Feed: Heat treated 20% USP lactic acid; Feed flow rate: 0.1 cc/mi; Temp: 330C; Catalyst volume: 3 cc. As the results shown in Table 7 indicate among the five different potassium phosphate compound tested, monobasic potassium phosphate (KH2PO4) at 2mmol/g of zeolite was found to be efficient doping agent in terms of resulting in the formation of acetaldehyde as the only major side product in the vapor phase dehydration reaction using lactic acid for the production acrylic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With alumina-doped tungstated mesoporous zirconia; In water; at 170℃;Inert atmosphere; | Batch catalytic experiments were performed under nitrogenatmosphere in tubular glass micro-reactors with pear-shaped bottomsand equipped with an appropriate PTFE-coated magneticstirring bar and a valve for gas purging. In a typical procedure, dxylose(30 mg), powdered catalyst (20 mg) and either water (1 mL,denoted W) or a solvent mixture (denoted W-T) comprising H2O(0.3 mL) and toluene (0.7 mL) were added to the reactor. The reactionmixtures were heated with a thermostatically controlled oilbath under magnetic stirring at 700 rpm, which was optimisedto avoid external mass transfer limitations; e.g. for ZrW(Cl), theinitial reaction rates (based on conversion at 30 min reaction)were similar for stirring rates at or above 700 rpm (9.4, 12.4 and12.1 mmol gcat-1 h-1 at 500, 700 and 900 rpm, respectively). Zerotime (considered as the instant the reaction began) was taken to bethe instant the micro-reactor was immersed in the oil bath. Aftera batch run, the catalyst was separated from the reaction mixtureby centrifugation, thoroughly washed with deionised water andfinally dried at 55 C overnight (giving the washed/dried solid) andcalcined at 450 C (1 C min-1) for 5 h (giving the recovered solid).The products present in the aqueous phase were analysed usinga Knauer K-1001 HPLC pump and a PL Hi-Plex H 300 mm × 7.7 mm(i.d.) ion exchange column (Polymer Laboratories Ltd., UK), coupledto a Knauer 2300 differential refractive index detector (for xylose)and a Knauer 2600 UV detector (280 nm, for Fur). The mobile phasewas 0.001 M H2SO4. The analytical conditions were the following:flow rate 0.6 mL min-1, column temperature 65 C. The Fur presentin the organic phase was quantified using a Gilson 306 HPLC pumpand a Spherisorb ODS S10 C18 column, coupled to a Gilson 118UV-vis detector (280 nm). The mobile phase consisted of 37% v/vmethanol and 63% v/v H2O (flow rate of 0.5 mL min-1). Authenticsamples of d-xylose and Fur were used as standards and calibrationcurves were used for quantification. The Fur yield (%) was calculatedusing the formula: [(moles of Fur formed)/(initial moles ofxylose)×100]. For each reaction time, at least two replicates ofan individual experiment were made; the reported results are theaverage values. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 25℃; for 14h; | General procedure: To a solution of aldehyde or isatin (1.0 mmol) in DMSO (1.0 mL), 1,2-diketone (1.0mmol) was added, followed by N,N?-diisopropylethylamine (0.2 mmol) at room temperature(25 C). The mixture was stirred at the same temperature as indicated in the Schemes until thealdehyde or isatin was mostly consumed. The mixture was diluted with EtOAc (5 mL) andwashed with water (5 mL) and brine (2 x 5 mL). The organic layer was dried over Na2SO4,filtered, concentrated under reduced pressure, and purified by silica gel flash columnchromatography to afford the aldol product(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 25℃; for 14h; | General procedure: To a solution of aldehyde or isatin (1.0 mmol) in DMSO (1.0 mL), 1,2-diketone (1.0mmol) was added, followed by N,N?-diisopropylethylamine (0.2 mmol) at room temperature(25 C). The mixture was stirred at the same temperature as indicated in the Schemes until thealdehyde or isatin was mostly consumed. The mixture was diluted with EtOAc (5 mL) andwashed with water (5 mL) and brine (2 x 5 mL). The organic layer was dried over Na2SO4,filtered, concentrated under reduced pressure, and purified by silica gel flash columnchromatography to afford the aldol product(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With pyrrolidine; acetic acid; In tetrahydrofuran; at 25℃; for 48h; | General procedure: a solution of aldehyde (1.0 mmol) in THF (1.0 mL), 1,2-diketone (1.0 mmol) was added followed by acetic acid (0.2 mmol) and pyrrolidine (0.2 mmol) at room temperature (25 C). The mixture was stirred at the same temperature for 48 h. The mixture was diluted with EtOAc (5 mL) and washed with water (5 mL) and brine (2 x 5 mL). The organic layer was dried over Na2SO4,filtered, concentrated under reduced pressure, and purified by silica gel flash columnchromatography to afford the aldol product(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 25℃; for 2h; | General procedure: To a solution of aldehyde or isatin (1.0 mmol) in DMSO (1.0 mL), 1,2-diketone (1.0mmol) was added, followed by N,N?-diisopropylethylamine (0.2 mmol) at room temperature(25 C). The mixture was stirred at the same temperature as indicated in the Schemes until thealdehyde or isatin was mostly consumed. The mixture was diluted with EtOAc (5 mL) andwashed with water (5 mL) and brine (2 x 5 mL). The organic layer was dried over Na2SO4,filtered, concentrated under reduced pressure, and purified by silica gel flash columnchromatography to afford the aldol product(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | Lithium carbonate (9.00 g, 176.5 mmol) was placed in a flask and dried at 300 C for 24 h. Toluene (10 mL), <strong>[600-14-6]2,3-pentanedione</strong> (2.00 g, 20 mmol), and anhydrous triethylamine (2.02 g, 20 mmol) were added. The mixture was protected from light and stirred for 30 min. The appropriate aryl isocyanate (30 mmol) dissolved in anhydrous toluene (5 mL) was added drop by drop (for 20 min) into the reaction mixture and stirred at room temperature for 18 h. The mixture was filtered through Celite and extracted with CH2Cl2 (3*15 mL). The organic extracts were combined, dried over Na2SO4, and the solvent was removed under vacuum. The final product was purified by column chromatography (SiO2 with 10% triethylamine, hexane/AcOEt, 95:5) to afford the corresponding exo-2-oxazolidinone diene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Lithium carbonate (9.00 g, 176.5 mmol) was placed in a flask and dried at 300 C for 24 h. Toluene (10 mL), <strong>[600-14-6]2,3-pentanedione</strong> (2.00 g, 20 mmol), and anhydrous triethylamine (2.02 g, 20 mmol) were added. The mixture was protected from light and stirred for 30 min. The appropriate aryl isocyanate (30 mmol) dissolved in anhydrous toluene (5 mL) was added drop by drop (for 20 min) into the reaction mixture and stirred at room temperature for 18 h. The mixture was filtered through Celite and extracted with CH2Cl2 (3*15 mL). The organic extracts were combined, dried over Na2SO4, and the solvent was removed under vacuum. The final product was purified by column chromatography (SiO2 with 10% triethylamine, hexane/AcOEt, 95:5) to afford the corresponding exo-2-oxazolidinone diene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Lithium carbonate (9.00 g, 176.5 mmol) was placed in a flask and dried at 300 C for 24 h. Toluene (10 mL), <strong>[600-14-6]2,3-pentanedione</strong> (2.00 g, 20 mmol), and anhydrous triethylamine (2.02 g, 20 mmol) were added. The mixture was protected from light and stirred for 30 min. The appropriate aryl isocyanate (30 mmol) dissolved in anhydrous toluene (5 mL) was added drop by drop (for 20 min) into the reaction mixture and stirred at room temperature for 18 h. The mixture was filtered through Celite and extracted with CH2Cl2 (3*15 mL). The organic extracts were combined, dried over Na2SO4, and the solvent was removed under vacuum. The final product was purified by column chromatography (SiO2 with 10% triethylamine, hexane/AcOEt, 95:5) to afford the corresponding exo-2-oxazolidinone diene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Lithium carbonate (9.00 g, 176.5 mmol) was placed in a flask and dried at 300 C for 24 h. Toluene (10 mL), <strong>[600-14-6]2,3-pentanedione</strong> (2.00 g, 20 mmol), and anhydrous triethylamine (2.02 g, 20 mmol) were added. The mixture was protected from light and stirred for 30 min. The appropriate aryl isocyanate (30 mmol) dissolved in anhydrous toluene (5 mL) was added drop by drop (for 20 min) into the reaction mixture and stirred at room temperature for 18 h. The mixture was filtered through Celite and extracted with CH2Cl2 (3*15 mL). The organic extracts were combined, dried over Na2SO4, and the solvent was removed under vacuum. The final product was purified by column chromatography (SiO2 with 10% triethylamine, hexane/AcOEt, 95:5) to afford the corresponding exo-2-oxazolidinone diene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.8% | With acetic acid; In ethanol;Reflux; | General procedure: The ligands were synthesized by the following common procedure, exemplifiedby the synthetic route used for glyoxalbis(thiosemicarbazone)(GTS). Thiosemicarbazide (10 mmol) was dissolved in ethanol(10 mL) and the appropriate diketone (5mmol) was dissolved in ethanol(5 mL) and the two solutions then mixed. Glacial acetic acid (5-6drops) was added and the mixture gently refluxed for 2 to 5 h. The mixturewascooled to roomtemperature and allowed to stand at 4 C overnightto ensure complete precipitation. The product was filtered off andwashedwith distilledwater (2 × 10 mL) and ethanol (10 mL) and driedin vacuo. |
4.5 g | With hydrogenchloride; In methanol; water; at 20℃; for 72h; | General procedure: Concentrated hydrochloric (2 mL) was added to a flask containing glyoxal (1.16 g, 20 mmol) and methanol (50 mL).The mixture was stirred at room temperature to form a homogenous solution. To this mixture, a solution of thiosemicarbazide (3.6 g, 40 mmol) dissolved in methanol containing 2 N hydrochloric acid was added, and the contents stirred at room temperature for 3 days, resulting in the formation of a white precipitate. The precipitated thiosemicarbazone was filtered, washed with methanol, and dried under vacuum. |
General procedure: Concentrated hydrochloric acid (2 mL) was added to a flask containing an appropriate mass of diketone (Scheme 1, generally millimolar amounts) and methanol (50 mL) and stirred at room temperature to form a homogenous solution. To thismixture, 4-aminophenyl thiosemicarbazide (dissolved in methanol containing 2 M hydrochloric acid) was added and the contents stirred at room temperature for 3 days, resulting in the formation of a colourless precipitate. The bis-thiosemicarbazone was filtered off, washed with methanol, and dried under vacuum.[45] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With acetic acid; In ethanol;Reflux; | General procedure: The ligands were synthesized by the following common procedure, exemplifiedby the synthetic route used for glyoxalbis(thiosemicarbazone)(GTS). Thiosemicarbazide (10 mmol) was dissolved in ethanol(10 mL) and the appropriate diketone (5mmol) was dissolved in ethanol(5 mL) and the two solutions then mixed. Glacial acetic acid (5-6drops) was added and the mixture gently refluxed for 2 to 5 h. The mixturewascooled to roomtemperature and allowed to stand at 4 C overnightto ensure complete precipitation. The product was filtered off andwashedwith distilledwater (2 × 10 mL) and ethanol (10 mL) and driedin vacuo. |
General procedure: Concentrated hydrochloric acid (2 mL) was added to a flask containing an appropriate mass of diketone (Scheme 1, generally millimolar amounts) and methanol (50 mL) and stirred at room temperature to form a homogenous solution. To thismixture, 4-aminophenyl thiosemicarbazide (dissolved in methanol containing 2 M hydrochloric acid) was added and the contents stirred at room temperature for 3 days, resulting in the formation of a colourless precipitate. The bis-thiosemicarbazone was filtered off, washed with methanol, and dried under vacuum.[45] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; | General procedure: To a solution of 2-azidobenzaldehyde 1 (0.44 g, 3mmol) and catalytic amount of piperidine (2 drops) in dry tetrahydrofuran at room temperature (15 mL), carbonyl compound (3 mmol) in dry tetrahydrofuran (5 mL) was added under nitrogen. The Knoevenagel reaction was carried out smoothly and the condensation was completed within 2 hours. And then triphenylphosphine (0.79 g, 3 mmol) was added to the mixture at the reflux temperature without the isolation of the Knoevenagel product, and with the end of the nitrogen evolution of the Staudinger reaction, the solution was heated at reflux for a reasonable time to complete the intramolecular aza-Wittig reaction to afford quinoline derivatives. After the completion of the reaction (monitoring by TLC), the solvent was evaporated, and the residue was purified by recrystallization from dichloromethane/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In methanol at 0℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In toluene; at 110℃; for 6h;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube fitted with a Teflon vacuum stopcock and microstirbar was flame-heated under vacuum and refilled with Ar.Vicinal diketones 2 (0.50 mmol) and 1.5 mL of anhydrous toluene was added at ice bath temperature. After 20 min, 1.2equiv of carbamoylsilane (0.60 mmol) was added, and the reaction mixture was stirred at 110 C until complete consumption of the carbamoylsilane (TLC). Volatiles were then removed under vacuum and the residue was chromatographed using PE-EtOAc as eluent to obtain beta-keto-alpha-siloxyamides 3 (or 5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In toluene; at 110℃; for 8h;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube fitted with a Teflon vacuum stopcock and microstirbar was flame-heated under vacuum and refilled with Ar.Vicinal diketones 2 (0.50 mmol) and 1.5 mL of anhydrous toluene was added at ice bath temperature. After 20 min, 1.2equiv of carbamoylsilane (0.60 mmol) was added, and the reaction mixture was stirred at 110 C until complete consumption of the carbamoylsilane (TLC). Volatiles were then removed under vacuum and the residue was chromatographed using PE-EtOAc as eluent to obtain beta-keto-alpha-siloxyamides 3 (or 5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; for 2h; | In the first set of experiments, NaZSM-5 zeolite was modified by impregnating one of the five different potassium phosphate compounds as provided in Table 7 and each of the modified NaZSM-5 zeolites was tested for their efficiency in vapor phase dehydration reaction. The vapor phase dehydration reaction using lactic acid as a reactant was carried out using the following experimental parameters: Gas flow rate: 55cc/mm; Feed: Heat treated 20% USP lactic acid; Feed flow rate: 0.1 cc/mi; Temp: 330C; Catalyst volume: 3 cc. As the results shown in Table 7 indicate among the five different potassium phosphate compound tested, monobasic potassium phosphate (KH2PO4) at 2mmol/g of zeolite was found to be efficient doping agent in terms of resulting in the formation of acetaldehyde as the only major side product in the vapor phase dehydration reaction using lactic acid for the production acrylic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With ammonium sulfate; In water; for 1h;Reflux; | General procedure: Ammonium sulfate (2 eq.) was dissolved in water (4 M) and the appropriate aldehyde (2a-d, 1 eq.) was added. Diketone (1a-d, 1 eq.) was added to the solution and the reaction mixture was stirred for 16 h at r.t. (or refluxed for 1 h when formaldehyde 2a was used). The reaction was cooled and made alkaline with NaOH (2 eq.), extracted with EtOAc (3 x 100 mL), and dried over MgSO4. Solvent was removed in vacuo and the product was purified. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With ammonium sulfate; In water; at 20℃; for 16h; | General procedure: Ammonium sulfate (2 eq.) was dissolved in water (4 M) and the appropriate aldehyde (2a-d, 1 eq.) was added. Diketone (1a-d, 1 eq.) was added to the solution and the reaction mixture was stirred for 16 h at r.t. (or refluxed for 1 h when formaldehyde 2a was used). The reaction was cooled and made alkaline with NaOH (2 eq.), extracted with EtOAc (3 x 100 mL), and dried over MgSO4. Solvent was removed in vacuo and the product was purified. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With indium(III) triflate; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 100℃; for 2h;Ionic liquid; | General procedure: An appropriate 2-aminoarylketone (1, 1 mmol) and <strong>[600-14-6]pentan-2,3-dione</strong> (4, 1.2 mmol) were reacted with In(OTf)3 (1.5 mmol) and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) (1.0 mmol) in 100 C for 2 h. The completion of reaction was monitored by TLC. The obtained product was extracted from the ionic liquid phases using ethyl acetate as a solvent. The product was isolated through distillation of ethyl acetate solution under reduced pressure and the ionic liquid medium was again used for the next cycle of reaction. Evaporation of the solvent was followed by purification through column chromatography over silica gel using petroleum ether:ethyl acetate (99:1) as an eluant to yield the respective product of 6-chloro-4-aryl-2-propanoylquinoline (5). 6-Chloro-4-(2?-chlorophenyl)-2-propanoylquinoline (5a) White solid; Yield 84%, M.p. 128-130 C; (Lit M.p 128-130C) (Characterized by mmp, co-TLC and superimposable FT-IR spectrum). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With indium(III) triflate; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 100℃; for 2h;Ionic liquid; | General procedure: An appropriate 2-aminoarylketone (1, 1 mmol) and pentan-2,3-dione (4, 1.2 mmol) were reacted with In(OTf)3 (1.5 mmol) and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) (1.0 mmol) in 100 C for 2 h. The completion of reaction was monitored by TLC. The obtained product was extracted from the ionic liquid phases using ethyl acetate as a solvent. The product was isolated through distillation of ethyl acetate solution under reduced pressure and the ionic liquid medium was again used for the next cycle of reaction. Evaporation of the solvent was followed by purification through column chromatography over silica gel using petroleum ether:ethyl acetate (99:1) as an eluant to yield the respective product of 6-chloro-4-aryl-2-propanoylquinoline (5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With indium(III) triflate; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 100℃; for 2h;Ionic liquid; | General procedure: An appropriate 2-aminoarylketone (1, 1 mmol) and <strong>[600-14-6]pentan-2,3-dione</strong> (4, 1.2 mmol) were reacted with In(OTf)3 (1.5 mmol) and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) (1.0 mmol) in 100 C for 2 h. The completion of reaction was monitored by TLC. The obtained product was extracted from the ionic liquid phases using ethyl acetate as a solvent. The product was isolated through distillation of ethyl acetate solution under reduced pressure and the ionic liquid medium was again used for the next cycle of reaction. Evaporation of the solvent was followed by purification through column chromatography over silica gel using petroleum ether:ethyl acetate (99:1) as an eluant to yield the respective product of 6-chloro-4-aryl-2-propanoylquinoline (5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.1% | In chloroform; at 6 - 8℃; for 5h; | 530.9 g (3.89 mol) of a 33% ethylamine aqueous solution and 398 g (3.33 mol) of trichloromethane were loaded into a 2 L 4-necked flask and cooled to about 6 C. 111 g (1.11 mol) of <strong>[600-14-6]ethyl methyl diketone</strong> (<strong>[600-14-6]2,3-pentanedione</strong>) was added dropwise to this solution at a liquid temperature of 6 to 8 C. for 1.5 hours. After the end of the dropping, the mixture was stirred at a liquid temperature of 6 to 8 C. for 3.5 hours. Thereafter, the reaction solution was allowed to stand and the organic layer was separated. Further, the aqueous layer was extracted twice with trichloromethane (100 g), and the organic layer was recovered. All the organic layers were combined, dehydrated with sodium sulfate (an appropriate amount) and filtered, and the solvent was removed at an oil bath temperature of 60 to 70 C. under a slightly reduced pressure. Thereafter, distillation was performed at an oil bath temperature of 70 C. under a reduced pressure. The obtained fraction was a pale yellow transparent liquid. The yield was 68.7 g and the percentage yield was 40.1%. (Analytical Data) (0100) (1) Mass spectrometry m/z: 154 (M+) (0101) (2) Elemental analysis C: 69.7 mass %, H: 11.4 mass %, N: 18.0 mass % (theoretical values; C: 70.0 mass %, H: 11.8 mass %, N: 18.2 mass %) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.79 g | In a 1-Lround-bottom flask connected to an argon/vacuum line, andequipped with a 10 cm-long Pyrex finger containing the lamp,EtOAc (950 mL) was thoroughly degassed (two freeze/pump/thaw cycles). Dione 21 (10 g, 100mmol), diluted with EtOAc(ca. 30 mL) was added with a syringe and, after the flask wastightly wrapped in a foil of aluminium, the resulting yellowsolution was irradiated with gentle stirring until the reactionwas complete (30 h), as indicated by disappearance of theyellow colour, almost as a titration. The solvents were eliminatedin a vacuum to give a 92/8 mixture (GC) of 18b and 22 respectively as a pale-yellow oil (10 g, 100%); IR (neat, cm1):3418, 1788; 13CNMR (CDCl3): delta 22.1, 28.1, 39.2, 88.3, 212.2;MS (CI-NH3): m/z 118 (M + NH4+), 101 (M + H+), 83, 72,55. Dimer 22: MS (CI-NH3): m/z 218 (M + NH4+), 201(M + H+), 183, 141, 127, 116, 99. In a flask connected to an argon line, 2,4,6-collidine (4.6 mL, 35mmol) was diluted with DMF (10 mL) and, with stirring, andcooling (ice bath), TESCl (5.8 mL, 35mmol) and the preceding 18b/22 mixture (2 g, 20 mmol), diluted with DMF (10 mL)were added sequentially with a syringe. The cooling bath was removed and the reaction mixture was further stirred at rt for 2 d before being diluted with 1MHCl (40 mL) and hexane (30 mL).After vigorous stirring, the aqueous layer was extracted withhexane (3 15 mL) and the pooled organic phases were washedwith brine (3 20 mL), and dried (MgSO4). The coloured residue left by evaporation of the solvents was purified bycolumn chromatography (hexane/EtOAc) to give, after thoroughelimination of the solvents in a vacuum, 18c as a colourlessoil (2.79 g, overall 65% from 21); TLC (hexane:ether =4:1) Rf = 0.58; IR (neat, cm-1): 1956, 1877, 1790, 1270, 1214,1039, 1013, 816, 744; 1H NMR (CDCl3): delta 0.5765(m, 6H),0.910.96(m, 9H), 1.43 (s, 3H), 2.022.09(m, 2H), 2.662.87(m, 2H); 13C NMR (CDCl3): delta 5.9 (CH2Si), 6.8 (CH3CH2), 23.9(CH3), 29.4 (C3H2), 38.8 (C4H2), 89.3 (C2), 210.5 (C=O); MS(CI-NH3): m/z 232 (M + NH4+), 215 (M + H+), 185, 157, 131,115, 102; Anal. Found: C, 61.87; H, 10.25%. Calcd forC11H22O2Si: C, 61.63; H, 10.34% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With acetic acid; at 20℃; | 367.9 mg (2.2 mmol) of 4-phenylthiosemicarbazide was added to the reaction flask, suspended in 4 mL of glacial acetic acid, and 100.1 mg (1.0 mmol) of 2,3-pentane was added thereto. Dione (<strong>[600-14-6]2,3-pentanedione</strong>) was added to the reaction flask, stirred at room temperature for condensation, and traced by thin layer chromatography (TLC) until the reaction was complete, followed by vacuum extraction. After filtration, the product was washed with fresh water and a small amount of ethyl alcohol to obtain a disulfide/semicarbazide ligand as a beige powder, which was dried and then weighed 299.5 mg (0.75 mmol). The yield was 75%. |
With hydrogenchloride; In methanol; at 20℃; for 72h; | General procedure: Concentrated hydrochloric acid (2 mL) was added to a flask containing 1.16 g of appropriate diketones (20 mmol) and anhydrous ethanol or methanol (50 mL). The mixture was stirred at room temperature to form a homogenous solution. To this mixture, a solution of phenyl thiosemicarbazide (3.6 g,40 mmol) dissolved in methanol containing 2N hydrochloric acid was added and the contents stirred at room temperature for 3 days, resulting in the formation of a colourless precipitate. The precipitated dithiosemicarbazone was filtered off, washed with methanol, and dried under vacuum. | |
General procedure: Concentrated hydrochloric acid (2 mL) was added to a flask containing an appropriate mass of diketone (Scheme 1, generally millimolar amounts) and methanol (50 mL) and stirred at room temperature to form a homogenous solution. To thismixture, 4-aminophenyl thiosemicarbazide (dissolved in methanol containing 2 M hydrochloric acid) was added and the contents stirred at room temperature for 3 days, resulting in the formation of a colourless precipitate. The bis-thiosemicarbazone was filtered off, washed with methanol, and dried under vacuum.[45] |
With hydrogenchloride; In methanol; water; | General procedure: Bis-thiosemicarbazones were prepared (compounds 1-3) bycondensing appropriately substituted diketones with 4-phenyl-3-thiosemicarbazide in methanol medium containing acatalytic amount of dilute hydrochloric acid. The precipitatedbis-thiosemicarbazone was washed with methanol,dried under vacuum and crystallized using methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With acetic acid; at 20℃; | 398.8 mg (2.2 mmol) of 4-(4-tolyl)thiosemicarbazide was added to the reaction flask, suspended in 4 mL of glacial acetic acid, and 100.1 mg ( 1.0 mmol) of <strong>[600-14-6]2,3-pentanedione</strong> was added to the above reaction flask, stirred at room temperature for condensation, and traced by thin layer chromatography (TLC) until the reaction. After complete filtration, the mixture was filtered through a vacuum, and the product was washed with fresh water and a small amount of ethyl alcohol to obtain a dithiocarbazone ligand as a white powder. After drying, the weight was 332.9 mg (0.78 mmol). The rate is 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With acetic acid; at 20℃; | 262.2 mg (2.2 mmol) of 4-ethylthiosemicarbazide was added to the reaction flask, dissolved in 3.5 mL of glacial acetic acid, and 100.1 mg (1.0 mmol) of 2,3-pentane was added. The ketone (<strong>[600-14-6]2,3-pentanedione</strong>) is added to the above reaction flask, stirred at room temperature for condensation reaction, and the reaction state is tracked by thin layer chromatography (TLC) until the reaction is complete, followed by filtration under reduced pressure. The product was washed with fresh water and a small amount of ice alcohol to obtain a white powder of disulfide-semicarbazole ligand. After drying, the weight was 272.9 mg (0.90 mmole), and the yield was 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; In methanol; at 50℃; for 1h;Inert atmosphere; | Ethyl 4-(4-formylcyclohexyl)-1,4-diazepane-1 -carboxylate (100 mg, 0.354 mmol) and <strong>[600-14-6]pentane-2,3-dione</strong>(42 mg, 0.425 mmol) were dissolved in MeOH (2 mE) and7 M methanolic ammonia (10 mE) was added. The reactionmixture was degassed with nitrogen and heated at 50 C. for1 h. The solvents were removed in vacuo and the residue waspurified by Prep HPEC [reverse phase HPEC (UPEC HERC18, 50x2.1 mm, 1.7 um, 0.4 mEpermin, gradient 10% to90% (over 3 mm), 100% (1 mm) then 10% (over 1 mm),0.1% NH3 in MeCN/water] to give ethyl 4-[4-(4-ethyl-5-methyl-i H-imidazol-2-yl)cyclohexyl]- 1 ,4-diazepane-1 -carboxylate, Example 5-1 isomer 1 (8 mg, 6.2%) as a colourlessgum and ethyl 4-[4-(4-ethyl-5-methyl-1 H-imidazol-2-yl)cy-clohexyl]- 1 ,4-diazepane-1 -carboxylate, Example 5-1 isomer2 (10 mg, 8.0%) as a colourless gum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.5% | At -5 to 3C,The above-prepared 2,3-pentanedione, ethylenediamine and anhydrous ethanol were mixed and stirred in a three-necked flask and reacted for 7 hours.After the reaction is over, the system is warmed to room temperature.Stirring at room temperature for 3h,Then warm up to 65-70 C, reflux 4h,After cooling is completed, cool rapidly to 30-40C.Then add xylene to the three-necked flask,Potassium hydroxide catalysts,After the addition is complete, continue to heat up to 65-70C,Reflux 5h,After the reaction is completed, it is cooled to room temperature.With suction filtration, the filtrate is distilled at atmospheric pressure.The distilled concentrate was diluted with saturated saline solution.extraction,Combine the organic phase,Dry with anhydrous copper sulfate, overfilter,Atmospheric pressure steamed extractant,Fractions from 55-60C/1.33 KMa were collected to give 2-ethyl-3-methylpyrazine;The product yield is over 93.5%;among them,The mass ratio of 2,3-pentanedione, ethylenediamine and anhydrous ethanol is 1:1.1:70;The mass ratio of 2,3-pentanedione, potassium hydroxide, catalyst and xylene was 1:0.8:2.8:1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.6% | It will be prepared by catalytic coupling to obtain 3-hydroxy-2-butanone, 3-hydroxy-2-pentanone, 2-hydroxy-3-pentanone and200 g of the mixed erotic product of 4-hydroxy-3-hexanone was placed in a 500 ml three-necked flask.The mass fractions are: 3-hydroxy-2-butanone 28%, 3-hydroxy-2-pentanone 33%, 2-hydroxy-3-pentanone 20.8%,4-hydroxy-3-hexanone 18.2%, adding 72 g (4 mol) of water and 1.8 g (0.03 mol) of cocatalyst acetic acid,The three-necked flask was placed in a water bath, stirred at 10 C, and reacted with ozone.Maintain the ozone flow rate of 0.3 L/min, and follow the progress of the reaction with gas chromatography. When the reaction is over,The sodium peroxide is added to remove the peroxygen value, and the distillation is carried out under reduced pressure.2,3-pentanedione finished product,Its yield relative to the autism was 51.6%. | |
512 g of acetaldehyde (11.636 mol), 488 g of propionaldehyde (8.414 mol) and 10 g of 3-ethyl 4-methyl-5-hydroxyethyl thiazole chloride (0.048 mol) are added into a 2.5 L of high pressure reactor, the pH value of a reaction solution is adjusted with sodium bicarbonate to 9-10, stirring is started, the temperature is raised to 120 C., a reaction starts spontaneously, the pressure of the reactor gradually rises to 1.5 MPa, and drops to 0 Mpa after 3.5 hours, it is indicated that the reaction is basically completed, and the reaction is stopped. After natural cooling, a crude product is further distilled under reduced pressure to obtain a mixed acyloin product of 3-hydroxy-2-butanone, 3-hydroxy-2-pentanone, 2-hydroxy-3-pentanone and 4-hydroxy-3-hexanone. 200 g of the mixed acyloin product containing 3-hydroxy-2-butanone, 3-hydroxy-2-pentanone, 2-hydroxy-3-pentanone and 4-hydroxy-3-hexanone, which is obtained through catalytic coupling, is added into a 500 ml of three-necked flask, wherein the mixed acyloin product contains, by mass, 28% of 26 3-hydroxy-2-butanone, 33% of 24 3-hydroxy-2-pentanone, 20.8% of 9 2-hydroxy-3-pentanone and 18.2% of 10 4-hydroxy-3-hexanone; then 72 g (4 mol) of 27 water and 1.8 g (0.03 mol) of 28 acetic acid serving as a cocatalyst are further added, the three-necked flask is placed in a water bath pot, stirring is conducted by maintaining a temperature at 10 C., and 17 ozone is introduced to start a reaction. An ozone flow rate is maintained at 0.3 L/min, a reaction process is tracked by gas chromatography, 29 sodium bisulfite is added after completion of the reaction to remove a peroxygen value, vacuum distillation separation is conducted to obtain a finished product of 4 2,3-pentanedione, and the yield of the finished product relative to acyloin is 51.6%. Product characterization data is as follows: 1H NMR (400 MHz, CDCl3): delta 2.78 (2H, d, -CH2-); delta 2.34 (3H, q, -CH3); delta 1.11 (3H, t, -CH3). 13C NMR (100 MHz, CDCl3): delta=199.8, 197.6, 29.3, 23.7, 7.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | General procedure: To a stirred mixture of lithium carbonate (9 g. 176 mmol) and 1 mL of <strong>[600-14-6]2,3-pentanedione</strong> (10 mmol) in dry Toluene under Nitrogen atmosphere, 2 g of triethylamine (2.8 ml, 20 mmol) were added, then the reaction was kept away from light and stirred for 30 minutes. A solution of the corresponding isocianate (15 mmol) in 2 mL of toluene or dioxane (4-chlorophenylisocyanate) was add dropwise for 10 minutes. After 20 hours of reaction the mixture is filter over celite, washing the filtrate with CH2Cl2, and the residue concentrated and purified by column chromatography using 10% triethylamine silica. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; at 100℃; under 22502.3 Torr; for 5h;Inert atmosphere; | In Examples 1 to 7, the acrylic acid synthesis reaction was performed using the solid strong acid cation exchange resins described in Table 1 below. First, the solid strong acid cation exchange resin was quantified at 0.05% by weight (based on the feed amount) and dried in an oven at 75 C. for 24 hours.The solid strong acid cation exchange resin, 1 mol of lactide, and 1.5 mol of acetic acid, which were dried and pretreated, were placed in a reactor, and the reactor was replaced with nitrogen and reacted at a reaction temperature of 100 C. at a pressure of 30 bar for 5 hours. After the reaction was completed, when the solid catalyst settled in the reactor, the product was filtered to remove the solid catalyst. The experimental results are shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; at 100℃; under 22502.3 Torr; for 5h;Inert atmosphere; | General procedure: In Examples 1 to 7, the acrylic acid synthesis reaction was performed using the solid strong acid cation exchange resins described in Table 1 below. First, the solid strong acid cation exchange resin was quantified at 0.05% by weight (based on the feed amount) and dried in an oven at 75 C. for 24 hours.The solid strong acid cation exchange resin, 1 mol of lactide, and 1.5 mol of acetic acid, which were dried and pretreated, were placed in a reactor, and the reactor was replaced with nitrogen and reacted at a reaction temperature of 100 C. at a pressure of 30 bar for 5 hours. After the reaction was completed, when the solid catalyst settled in the reactor, the product was filtered to remove the solid catalyst. The experimental results are shown in Table 1. | |
With acetic acid; at 100℃; under 22502.3 Torr; for 5h;Inert atmosphere; | General procedure: Two solid strongly acidic cation exchange resins, 1 mol of lactide and 1 mol of acetic acid, which were dried and pretreated, were placed in a reactor, and the reactor was replaced with nitrogen and reacted for 5 hours at a pressure of 30 bar at a reaction temperature of 100 C. After the reaction was completed, when the solid catalyst settled in the reactor, the product was filtered to remove the solid catalyst. The experimental results are shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; at 100℃; under 22502.3 Torr; for 5h;Inert atmosphere; | In Examples 1 to 7, the acrylic acid synthesis reaction was performed using the solid strong acid cation exchange resins described in Table 1 below. First, the solid strong acid cation exchange resin was quantified at 0.05% by weight (based on the feed amount) and dried in an oven at 75 C. for 24 hours.The solid strong acid cation exchange resin, 1 mol of lactide, and 1.5 mol of acetic acid, which were dried and pretreated, were placed in a reactor, and the reactor was replaced with nitrogen and reacted at a reaction temperature of 100 C. at a pressure of 30 bar for 5 hours. After the reaction was completed, when the solid catalyst settled in the reactor, the product was filtered to remove the solid catalyst. The experimental results are shown in Table 1. | |
With acetic acid; at 100℃; under 22502.3 Torr; for 5h;Inert atmosphere; | General procedure: Two solid strongly acidic cation exchange resins, 1 mol of lactide and 1 mol of acetic acid, which were dried and pretreated, were placed in a reactor, and the reactor was replaced with nitrogen and reacted for 5 hours at a pressure of 30 bar at a reaction temperature of 100 C. After the reaction was completed, when the solid catalyst settled in the reactor, the product was filtered to remove the solid catalyst. The experimental results are shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; at 100℃; under 22502.3 Torr; for 5h;Inert atmosphere; | General procedure: Two solid strongly acidic cation exchange resins, 1 mol of lactide and 1 mol of acetic acid, which were dried and pretreated, were placed in a reactor, and the reactor was replaced with nitrogen and reacted for 5 hours at a pressure of 30 bar at a reaction temperature of 100 C. After the reaction was completed, when the solid catalyst settled in the reactor, the product was filtered to remove the solid catalyst. The experimental results are shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formate dehydrogenase from Candida boidinii; sodium formate; R-selective 2,3-butanediol dehydrogenase from Bacillus clausii DSM 8716<SUP>T</SUP>; NADH In methanol at 30℃; for 48h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With transaminase; pyridoxal 5'-phosphate In dimethyl sulfoxide at 30℃; for 72h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With transaminase; pyridoxal 5'-phosphate In dimethyl sulfoxide at 30℃; for 72h; Enzymatic reaction; |
Tags: 600-14-6 synthesis path| 600-14-6 SDS| 600-14-6 COA| 600-14-6 purity| 600-14-6 application| 600-14-6 NMR| 600-14-6 COA| 600-14-6 structure
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Code | Phrase |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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