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[ CAS No. 20587-30-8 ] {[proInfo.proName]}

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Chemical Structure| 20587-30-8
Chemical Structure| 20587-30-8
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Product Details of [ 20587-30-8 ]

CAS No. :20587-30-8 MDL No. :MFCD00157275
Formula : C9H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 195.17 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 20587-30-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.51
TPSA : 72.12 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.02
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : 1.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.706 mg/ml ; 0.00362 mol/l
Class : Soluble
Log S (Ali) : -3.16
Solubility : 0.134 mg/ml ; 0.000689 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.25
Solubility : 1.11 mg/ml ; 0.00568 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 20587-30-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273 UN#:N/A
Hazard Statements:H302-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20587-30-8 ]

* 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.

  • Downstream synthetic route of [ 20587-30-8 ]

[ 20587-30-8 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 67-56-1 ]
  • [ 3113-72-2 ]
  • [ 20587-30-8 ]
YieldReaction ConditionsOperation in experiment
93% With sulfuric acid; at 0 - 90℃; for 16.0h; A solution of 5-methyl-2-nitrobenzoic acid (8 g, 44.198 mmol) in methanol (80 mL) was cooled to 0C. Sulfuric acid (5 mL) was added to the mixture drop wise. The mixture was heated to 90C and stirred for 16 h. Progress of the reaction was followed by TLC (50% ethyl acetate/hexane). After completion of the reaction, excess methanol was evaporated and the residue was poured into water (150 mL) and extracted with ethyl acetate (150 mL x 2). The combined organic layers were washed with saturated NaHC03 solution (50 mL x 2), followed by brine (20 mL). The organic layer was dried over Na2S04, filtered and evaporated to give methyl 5-methyl-2-nitrobenzoate (Yield: 8 g, 93 %). 1H NMR (400 MHz, CDC13): delta 7.86-7.84 (d, 1H, J=8 Hz), 7.48 (s, 1H), 7.40-7.38 (d, 1H, J=8 Hz), 3.91 (s, 3H), 3.47 (s, 3H).
With thionyl chloride; at -20℃; for 48.0h;Heating / reflux; At temperature of -20C or less, 5-methyl-2-nitrobenzoic acid (18.1g) was added to methanol (100ml) to which thionyl chloride (10ml) have been added was refluxed for 2 days. A crystal extracted from the radiationally cooled reactive mixture was removed by filtration followed to be washed in clear water. A title compound (13.1g) having the following physical properties values was obtained. TLC: Rf 0.46 (n-hexane: ethyl acetate =4:1); NMR (CDCl3):delta 7.87 (d, J = 8.1 Hz, 1H), 7.48 (d, J = 1.5 Hz, 1H), 7.40 (m, 1H), 3.92 (s, 3H), 2.47 (s, 3H)
  • 2
  • [ 20587-30-8 ]
  • [ 18595-16-9 ]
YieldReaction ConditionsOperation in experiment
60% With ammonium chloride; zinc; In methanol; water; at 0 - 20℃; for 12.0h; A solution of <strong>[20587-30-8]methyl 5-methyl-2-nitrobenzoate</strong> (8 g, 41.025 mmol) in methanol (80 mL) and water (10 mL) was cooled to 0C. Zinc powder (13.33 g, 205.128 mmol) was then added, followed by NH4C1 (17.6 g, 328.2 mmol). The mixture was stirred for 12 h at rt. Progress of the reaction was followed by TLC (20% ethyl acetate/hexane). After completion of the reaction, the mixture was filtered and the filtrate was evaporated to provide crude residue. The crude reside was basified with saturated NaHC03 solution and extracted with DCM (2 x 20 mL). The combined organic layers were dried over Na2S04, filtered and evaporated to give methyl 2-amino-5-methylbenzoate (Yield: 4 g, 60%).1H NMR (400 MHz, CDC13): delta 7.65 (s, 1H), 7.25 (s, 1H), 7.10-7.07 (q, 1H, J=8 Hz), 6.58 (d, 1H), 3.86 (s, 3H), 2.22 (s, 3H).
With hydrogen;5% palladium-on-charcoal; In ethyl acetate; for 8.0h; A mixture of which under argon gas 5% palladium carbon (1.55g) has been added to the compound (5.85g) prepared in Reference example 13, which ethyl acetate (150ml) had been added, was stirred for 8 hours under hydrate gas. The reactive mixture filtered with celite was concentrated. A title compound (4.89g) having the following physical properties values was obtained. TLC:Rf 0.44 (n-hexane: ethyl acetate =6:1); NMR (CDCl3):delta 7.66 (dd, J = 1.8 Hz, 0.6 Hz, 1H), 7.10 (m, 1H), 6.59 (d, J = 8.7 Hz, 1H), 5.56 (bs, 1H), 3.86 (s, 3H), 2.23 (s, 3H)
  • 3
  • [ 20587-30-8 ]
  • [ 88071-91-4 ]
YieldReaction ConditionsOperation in experiment
85% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In benzene;Heating / reflux; 52 (2.Og, 10.2mmol) in 10OmL benzene was stirred at room temperature. NBS (1.99g, 11.2mmol) and AIBN (0.084g, 0.51mmol) were added respectively. The reaction mixture was refluxed overnight. The benzene was evaporated (rotavap) under vacuum. The crude material was extracted with ethyl acetate and washed with IM NaOH. The organic layer was washed with brine, dried (Na2SO4), concentrated, and dried under vacuum to give methyl 5-(bromomethyl)-2-nitrobenzoate (53) as a brown oil (2.4g) in 85% yield. MS (M+NH4)+ 290,292
69% With N-Bromosuccinimide; In tetrachloromethane;Photolysis; [0128] 5-Methyl-2-nitro-benzoic acid methyl ester (1.6 g, 8 mmol) and bromosuccinimide (1.75 g, 9.8 mmol) were suspended in 80 mL of CCl 4. The solution was photolyzed overnight with a 300 watt lamp. The reaction solution was washed with saturated NaCl solution (3 20 mL) and dried over anhydrous Na 2SO 4. After evaporation, the residue was purified by flash silica gel column chromatography (hexanes/EtOAc, 10:1) to afford 3-methoxycarbonyl 4-nitrobenzyl bromide as a yellow solid (530 mg, 69%). m.p. 55-56° C.; 1H NMR (CDCl 3, 200 MHz) delta 3.95 (s, 3H), 4.52 (s, 2H), 7.66 (dd, 1H, J=1.8, 8.4 Hz), 7.76 (d, 1H, J=2.2 Hz), 7.92 (d, 1H, J=8.4 Hz).
55.6% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 85℃; for 4.0h; 5 g (0.025 mol, 1 eq) of <strong>[20587-30-8]methyl 5-methyl-2-nitrobenzoate</strong> and 6.2 g (0.025 mol, 1 eq) of benzoyl peroxide were dissolved in 50 mL of carbon tetrachloride until completely dissolved. 6.85 g (0.038 mol, 1.5 eq) of N-bromosuccinamide was dissolved in 40 mL of carbon tetrachloride, and then slowly added dropwise to the above mixture, and reacted at 85 C for 4 h. After cooling to room temperature, the mixture was filtered and dried, and a small amount of ethyl acetate was added to dissolve, and then a large amount of n-hexane was added to precipitate. The filtrate was collected by suction filtration, dried and purified by silica gel column using petroleum ether ethyl acetate system as eluent.Yielding 3.91 g of a yellow solid was product 6, yield 55.6%.
44.0% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); In acetic acid methyl ester; at 75 - 78℃; for 13.6667h; Step 1: A mixture of <strong>[20587-30-8]5-methyl-2-nitro-benzoic acid methyl ester</strong> (93.95 g, 481.35 mmol), 1,3-dibromo-5,5-dimethylhydantoin (75.70 g, 264.74 mmol), in methyl acetate (550 mL) was heated at 78 C. for 40 minutes while stirred with a mechanical stirrer. Then a solution of 2,2'-azobisisobutyro-nitrile (3.95 g, 24.07 mmol) in methyl acetate (80 mL) was added, and the mixture was heated at about 75 C. for 13 hours. The mixture was allowed to cooled to 15 C. and stirred for 2 hours to age the precipitate. The suspension was filtered, washed with 10 C. methyl acetate (2*50 mL) to give a brown filtrate. To the filtrate, was added heptane (500 mL). The organic layer was washed with 2% brine (2*500 mL) and water (2*500 mL), and concentrated to about 2 volumes. To the mixture, was added t-butyl methyl ether (or MTBE, 300 mL). The mixture was heated at about 70 C. for 15 minutes, cooled to about 53 C. over one hour, seeded with the product (about 250 mg, or simply re-crystallized) at 45 C., then at 20-25 C., while blowing nitrogen with a glass pipette overnight. The resulting solid was filtered via a medium pore-sized funnel, washed with a pre-cooled 10 C. mixed solvent of heptane/MTBE (1/2 vol/vol) and suction dried in hood overnight to give 5-bromomethyl-2-nitro-benzoic acid methyl ester as an off-white solid (58.3 g, 44.0% yield). The solid was used in the next step without further purification.
40% With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform;Reflux; Example 11. Preparation of N-((2-(4-hydroxy-3,5-dimethylphenyl)-4-oxo-3,4-dihydroquinazolin-6-yl)methyl)methanesulfonamide [0184] To a solution of <strong>[20587-30-8]methyl-5-methyl-2-nitrobenzoate</strong> (2.3 g, 11.8 mmol) in CHCI3 (150 mL) was added NBS (5.3 g, 30.0 mmol) and benzoyl peroxide (0.285 g, 1.2 mmol). The reaction was heated at reflux temperature overnight. Then, the resulting mixture was washed sequentially with H2O, Na2CO3, and brine. The organic layer was then dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% to 20% ethyl acetate/heptane, afforded methyl 5-(bromomethyl)-2-nitrobenzoate (1.3 g, 40%).[0185] To a solution of methyl 5-(bromomethyl)-2-nitrobenzoate (1.3 g, 4.7 mmol) in DMF (15 mL) was added potassium phthalimide (1.0 g, 5.2 mmol) and the reaction was stirred at room temperature for 1 hour and concentrated in vacuo. Purification by flash chromatography, eluting with 15% to 70% ethyl acetate/heptane, afforded methyl 5-((1,3-dioxoisoindolin-2-yl)methyl)-2-nitrobenzoate (1.4 g, 88%).[0186] A solution of methyl 5-((1 ,3-dioxoisoindolin-2-yl)methyl)-2- nitrobenzoate (0.50 g, 1.4 mmol) in EtOH (10 mL) was treated with hydrazine (0.14 mL, 4.4 mol) and the reaction was stirred at room temperature overnight. After this time, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluting with 30% to 100% of 92:7:1 CHCb/MeOH/concentrate NH4OH in CH2CI2, to afford methyl 5-(aminomethyl)-2-nitrobenzoate (0.23 g, 78%).[0187] To a solution of methyl 5-(aminomethyl)-2-nitrobenzoate (0.23 g, 1.1 mmol) in CH2CI2 (5 ml_) was added Et3N (0.31 ml_, 2.2 mmol) and methanesulfonyl chloride (0.08 ml_, 1.1 mmol). The reaction was stirred for 15 minutes at room temperature, concentrated in vacuo, and purified by flash chromatography on silica gel, eluting with 2% to 20% MeOH/CH2CI2, to afford methyl 5-(methylsulfonamidomethyl)-2-nitrobenzoate (0.18 g, 57%).[0188] A mixture of methyl 5-(methylsulfonamidomethyl)-2-nitrobenzoate (0.18 g, 0.62 mmol) in EtOH (10 mL) was flushed with N2. Pd/C (0.018 g) was added and the reaction was flushed with H2 for 2 hours. Then, the resulting mixture was filtered through celite and the filtrate was concentrated. Purification by flash chromatography, eluting with 15% to 60% of 92:7:1 CHCb/MeOH/concentrate NH4OH in CH2CI2, afforded methyl 2-amino-5-(methylsulfonamidomethyl)-benzoate (0.085 g, 53%).[0189] To a solution of methyl 2-amino-5-(methylsulfonamidomethyl)benzoate (0.085 g, 0.33 mmol) in THF (7 mL) and H2O (3 mL) was added LiOH-H2O (0.028 g, 0.65 mol). The reaction was stirred at room temperature for 2 hours and then neutralized with 1 N HCI. The resulting aqueous solution was extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated, to afford 2-amino-5-(methylsulfonamidomethyl)benzoic acid (0.066 g, 82%).[0190] A solution of 2-amino-5-(methylsulfonamidomethyl)benzoic acid (0.066 g, 0.27 mol) in THF (5 mL) was treated with EDCI (0.062 g, 0.32 mmol), HOBT (0.044 g, 0.32 mol) and NMM (0.035 mL, 0.32 mmol.) The reaction was stirred at room temperature for 1.5 hours. Then, NH4OH (0.03 mL, 0.35 mmol) in H2O (0.03 mL) was added. The mixture was stirred at room temperature for 5 hours and then concentrated. Purification by flash chromatography, eluting with 92:7:1 to 7:2.5:0.5 CHCI3/MeOH/concentrated NH4OH, afforded 2-amino-5- (methylsulfonamidomethyl)benzamide (0.035 g, 53%).[0191] A mixture of 2-amino-5-(methylsulfonamidomethyl)benzamide (0.035 g, 0.14 mmol), 4-hydroxy-3,5-dimethyl benzaldehyde (0.022 g, 0.14 mmol) and CuCI2 (0.039 g, 0.28 mmol) in EtOH (5 ml_) was refluxed for 3 h, then concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 92/7/1 CHCI3: MeOH xoncentrated NH4OH, followed by reverse-phase chromatography, eluting with 10% to 50% CH3CN in H2O with 0.1% TFA, and finally flash chromatography on silica gel, eluting with 7:2.5:0.5 CHCI3/MeOH/concentrated NH4OH, afforded the title compound (0.030 g, 57%) as a white solid. 1H NMR (300 MHz, DMSO-Cf6): delta 8.09 (s, 1 H), 7.83-7.90 (m, 2H), 7.65-7.78 (m, 3H), 6.81-7.54 (m, 2H), 4.30 (d, J = 6.2 Hz, 2H), 2.91 (s, 3H), 2.24 (s, 6H). ESI MS m/z 374 [M+H]+.
40% With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform;Reflux; To a solution of <strong>[20587-30-8]methyl-5-methyl-2-nitrobenzoate</strong> (2.3 g, 11.8 mmol) in CHCl3 (150 mL) was added NBS (5.3 g, 30.0 mmol) and benzoyl peroxide (0.285 g, 1.2 mmol). The reaction was heated at reflux temperature overnight. Then, the resulting mixture was washed sequentially with H2O, Na2CO3, and brine. The organic layer was then dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% to 20% ethyl acetate/heptane, afforded methyl 5-(bromomethyl)-2-nitrobenzoate (1.3 g, 40%)
With N-Bromosuccinimide; dibenzoyl peroxide; In benzene; for 4.0h;Reflux; To 1.0 g of the crude product of <strong>[20587-30-8]5-methyl-2-nitrobenzoic acid methyl ester</strong> synthesised in the foregoing step 1, there were added 1.4 g of N-bromosuccinimide, 0.5 g of benzoyl peroxide and 30 mL of benzene, the resulting mixture was refluxed with stirring for 4 hours and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 30 mL of acetonitrile, this solution was added to 36 mL of a 2M methylamine solution in THF and the mixture was further stirred at room temperature for 10 minutes. The solvent was distilled off under reduced pressure, then ethyl acetate was added, followed by the washing thereof four times with a 1M hydrochloric acid solution. The resulting ethyl acetate phase was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution and the solvent was distilled off under reduced pressure. The crude product thus prepared was dissolved in 30 mL of acetonitrile, 1.1 g of di-tert-butyl-dicarbonate and 1.1 mL of triethylamine were added to the solution and the resulting mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, ethyl acetate was added thereto, the insoluble matter was then removed through filtration and the filtrate thus obtained was concentrated under reduced pressure. The resulting crude product was purified by the silica gel chromatography (hexane: ethyl acetate=90:10-80:20) to thus give 0.71 g of the title compound. MS (ESI+): m/z 325 (MH+).
17.9 mg With N-Bromosuccinimide; carbon tetrabromide; dibenzoyl peroxide; for 4.0h;Reflux; 5-Methyl-2-nitrobenzoic acid methyl ester (27.1 g, 138.8 mmol) was dissolved in carbon tetrachioride (500 mE), and N-bromosuccinimide (29.6 g, 166.6 mmol) was added, followed by benzoyl peroxide (6.72 g, 27.7 mmol). The mixture was illuminated and gently refluxed for 4 hours. Then, the mixture was cooled and concentrated, then purified by column chromatography silica gel 230-400 mesh; 10% ethyl acetate in hexanes as eluent) to give 5-bromomethyl-2-ni- trobenzoic acid methyl ester. Yield: 17.9 g (47%).

  • 4
  • [ 20587-30-8 ]
  • [ 96134-70-2 ]
  • 5
  • [ 99-36-5 ]
  • [ 7697-37-2 ]
  • [ 5471-82-9 ]
  • [ 20587-30-8 ]
  • 7
  • [ 20587-30-8 ]
  • [ 88071-91-4 ]
  • [ 883529-87-1 ]
  • 9
  • [ 20587-30-8 ]
  • [ 883529-87-1 ]
  • 11
  • [ 20587-30-8 ]
  • 6,6'-bis(3,5-dimethoxybenzamido)-3,3'-ethanediyldibenzoic acid [ No CAS ]
  • 12
  • [ 20587-30-8 ]
  • [ 344779-35-7 ]
  • 13
  • [ 20587-30-8 ]
  • <i>N</i>-(5-methyl-3-oxo-3<i>H</i>-benzo[<i>c</i>]isoxazol-1-ylmethyl)-acetamide [ No CAS ]
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; ;