Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 205448-64-2 | MDL No. : | MFCD26395147 |
Formula : | C16H17NO7 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FLQIWMCFHBVQGR-UHFFFAOYSA-N |
M.W : | 335.31 | Pubchem ID : | 22646557 |
Synonyms : |
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.31 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 82.38 |
TPSA : | 100.16 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.73 cm/s |
Log Po/w (iLOGP) : | 2.79 |
Log Po/w (XLOGP3) : | 2.27 |
Log Po/w (WLOGP) : | 1.42 |
Log Po/w (MLOGP) : | 0.73 |
Log Po/w (SILICOS-IT) : | 1.99 |
Consensus Log Po/w : | 1.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.21 mg/ml ; 0.000625 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.01 |
Solubility : | 0.0328 mg/ml ; 0.0000977 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.79 |
Solubility : | 0.055 mg/ml ; 0.000164 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
96% | at 50℃; for 0.666667 h; Heating / reflux | The starting material was prepared as follows: 3-Methoxy-4-methoxycarbonylaniline (14.15 g, 78 mmol) was suspended in isopropanol and heated at 50° C. 2,2-Dimethyl-5-methoxymethylene-1,3-dioxane-4,6-dione (14.8 g, 80 mmol), (Montatsh. Chem. 1967, 98, 564), was then added in portions over 10 minutes and the mixture was heated at reflux for 30 minutes.. The mixture was left to cool to ambient temperature overnight.. The precipitate formed was collected by filtration, washed with isopropanol and dried under vacuum to give 5-((3-methoxy-4-methoxycarbonylanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (25.2 g, 96percent). |
95% | at 70℃; for 1 h; | Methyl 4-amino-2-methoxy-benzoate (1.07 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.0 g) were dissolved in 2-propanol (20 ml), and the mixture was stirred at 70°C for one hr. The solvent was removed by distillation under the reduced pressure, and the residue was washed with ether to give methyl 4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-2-methoxy-benzoate (1.71 g, yield 95percent). Methyl 4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino ]-2-methoxy-benzoate (1.70 g) and biphenyl (4.76 g) were suspended in diphenyl ether (15 ml), and the suspension was stirred at 240°C for one hr. The suspension was cooled to room temperature, and the precipitated crystal was collected by filtration and was washed with ether. The crystal thus obtained as such was used in the next reaction without further purification. N,N-Dimethylformamide (2 drops) was added to the crystal thus obtained. Further, phosphorus oxychloride (2.5 ml) was added thereto, and the mixture was stirred at 100°C for 2 hr. The solvent was removed by distillation under the reduced pressure, and water was added to the residue under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give methyl 4-chloro-7-methoxy-quinoline-6-carboxylate (707 mg, yield 55percent) (2 steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.62% | at 90℃; for 1 h; | Methyl 2-methoxy-4-amino-benzoate (500.00 g, 2.76 mol), 2,2-dimethyl-1,3-dioxane-4,6-dione (397.73 g, 2.76 mol) and trimethyl orthoformate (292.84 g, 2.76 mol) were added to isopropanol (5.00 L). The reaction solution was heated up to an outer temperature of 90 °C and kept refluxing for 1 hour. The completion of the reaction was detected by TLC. The reaction solution was cooled to an outer temperature of 20 °C in an ice bath and then filtered. The solid was washed with MTBE (300 ml * 2) and then concentrated to dryness in a water bath. Compound 1A (873.00 g, 2.47 mol, the yield was 89.62percent and the purity was 95percent) was obtained as a light red powder. NMR (DMSO) demonstrated that the product was correct. 1H NMR (400 MHz, DMSO-d6) ppm 1.67 (s, 6 H) 3.76 (s, 3 H) 3.86 (s, 3 H) 7.19 (dd, J=8.41, 1.63 Hz, 1 H) 7.43 (d, J=1.25 Hz, 1 H) 7.71 (d, J=8.28 Hz, 1 H) 8.69 (d, J=10.04 Hz, 1 H) 11.25 (d, J=9.03 Hz, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | at 40 - 190℃; for 1 h; | 5-((3-Methoxy-4-methoxycarbonylanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (10 g, 29.8 mmol) was suspended in DOWTHERM A, (trade mark of Fluka Chemie AG), (125 ml) and heated to 180-190° C. over 30 minutes.. The starting material dissolved at 100° C. and carbon dioxide came off at approximately 180° C. The heating was stopped after a further 30 minutes and the product precipitated out as the temperature dropped.. Upon reaching 40° C. ether was added and the mixture was stirred for 30 minutes.. The solid was collected by filtration, washed with ether and dried under vacuum to give 7-methoxy-6-methoxycarbonyl-1,4-dihydroquinolin-4-one (5.56 g, 80percent). 11H NMR Spectrum: (DMSOd6) 3.80 (s, 3H); 3.85 (s, 3H); 5.95 (d, 1H); 7.00 (s, 1H); 7.85 (d, 1H); 8.40 (s, 1H); 11.6 (br s, 1H); MS-ESI: 234 [MH]+; |
[ 909563-22-0 ]
Methyl 4-amino-2-isopropoxybenzoate
Similarity: 0.77
[ 59-06-3 ]
Methyl 4-acetamido-2-ethoxybenzoate
Similarity: 0.76
[ 889858-34-8 ]
tert-Butyl 4-amino-2-hydroxybenzoate
Similarity: 0.76
[ 4093-29-2 ]
Methyl 4-acetamido-2-methoxybenzoate
Similarity: 0.76
[ 27492-84-8 ]
Methyl 4-amino-2-methoxybenzoate
Similarity: 0.74
[ 25063-68-7 ]
2,2-Dimethyl-5-((pyridin-3-ylamino)methylene)-1,3-dioxane-4,6-dione
Similarity: 0.66
[ 54535-22-7 ]
Diethyl 2-((phenylamino)methylene)malonate
Similarity: 0.65
[ 1168150-46-6 ]
(E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate
Similarity: 0.63
[ 85920-63-4 ]
5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Similarity: 0.58
[ 127033-74-3 ]
N-(3-Methoxyphenyl)cinnamamide
Similarity: 0.58
[ 251107-30-9 ]
Methyl 6-methoxy-1H-indole-5-carboxylate
Similarity: 0.79
[ 909563-22-0 ]
Methyl 4-amino-2-isopropoxybenzoate
Similarity: 0.77
[ 205448-65-3 ]
Methyl 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate
Similarity: 0.76
[ 59-06-3 ]
Methyl 4-acetamido-2-ethoxybenzoate
Similarity: 0.76
[ 4093-29-2 ]
Methyl 4-acetamido-2-methoxybenzoate
Similarity: 0.76
[ 251107-30-9 ]
Methyl 6-methoxy-1H-indole-5-carboxylate
Similarity: 0.79
[ 909563-22-0 ]
Methyl 4-amino-2-isopropoxybenzoate
Similarity: 0.77
[ 205448-65-3 ]
Methyl 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate
Similarity: 0.76
[ 59-06-3 ]
Methyl 4-acetamido-2-ethoxybenzoate
Similarity: 0.76
[ 889858-34-8 ]
tert-Butyl 4-amino-2-hydroxybenzoate
Similarity: 0.76
[ 909563-22-0 ]
Methyl 4-amino-2-isopropoxybenzoate
Similarity: 0.77
[ 59-06-3 ]
Methyl 4-acetamido-2-ethoxybenzoate
Similarity: 0.76
[ 889858-34-8 ]
tert-Butyl 4-amino-2-hydroxybenzoate
Similarity: 0.76
[ 4093-29-2 ]
Methyl 4-acetamido-2-methoxybenzoate
Similarity: 0.76
[ 27492-84-8 ]
Methyl 4-amino-2-methoxybenzoate
Similarity: 0.74