Structure of 1917-15-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1917-15-3 |
Formula : | C6H6O3 |
M.W : | 126.11 |
SMILES Code : | C1=C(OC(=C1)C)C(O)=O |
MDL No. : | MFCD00092359 |
Boiling Point : | No data available |
InChI Key : | OVOCLWJUABOAPL-UHFFFAOYSA-N |
Pubchem ID : | 74710 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319-H412 |
Precautionary Statements: | P273-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 30.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
50.44 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.21 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.25 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.75 |
Solubility | 2.22 mg/ml ; 0.0176 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.91 |
Solubility | 1.56 mg/ml ; 0.0124 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.33 |
Solubility | 5.9 mg/ml ; 0.0468 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.18 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.17 |
* 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 |
---|---|---|
7%; 10%; 70% | With 0.43% Pd/C; hydrogen; In water; at 170℃; for 0.0025h;Autoclave; | EXAMPLES The following experiments were conducted in a stainless steel reactor wherein a bed of solid catalyst was placed. The catalyst bed was kept at the same temperature. Feedstock containing FDCA and FFCA was fed over the bed of catalyst. The feedstock was an aqueous stream containing 0.5 percentwt of crude FDCA composition. The crude FDCA composition consisted of 98.0 percentwt of FDCA, 1.0 percentwt of FFCA, and about 1.0 percentwt of the monomethyl ester of FDCA (FDCA-ME). The composition further contained some ppm of the components of the oxidation catalyst, viz. cobalt, manganese and bromine. Hydrogen-containing gas, consisting of 10 percentvol hydrogen and 90 percentvol nitrogen, was used for the hydrogenation. The catalysts used were Catalyst 1 , comprising 5 percentwt palladium on carbon and Catalyst 2, comprising 0.43 percentwt palladium on carbon. The experiments were conducted as follows. The reactor was charged with a desired load of the desired catalyst. The bed of catalyst was vented several times with hydrogen to remove any oxygen. Unless otherwise indicated, the reactor was subsequently pressurized with the hydrogen-containing gas to a pressure of 15 bar (at 20°C) and heated to the desired reaction temperature before the feedstock was passed over the bed of catalyst with the desired space velocity, expressed as weight hourly space velocity (WHSV) in grams of feedstock per gram of catalyst per hour. The Tables may also contain the contact time or residence time. EXAMPLE 1 In order to show the influence of the reaction temperature on the conversion of the FFCA to HMFA and MFA Catalysts 1 and 2 were used in experiments wherein the above feedstock was passed over beds of the two catalysts with different space velocities and at different reaction temperatures. From the reactor effluent the amounts of FFCA, HMFA and MFA were determined. The results are shown in Table 1. The amounts of FFCA, HMFA and MFA are expressed as mass percent, based on the amount of FFCA in the feedstock. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6%; 85% | With 0.43% Pd/C; hydrogen; In water; at 160℃; for 0.0025h;Autoclave; | EXAMPLES The following experiments were conducted in a stainless steel reactor wherein a bed of solid catalyst was placed. The catalyst bed was kept at the same temperature. Feedstock containing FDCA and FFCA was fed over the bed of catalyst. The feedstock was an aqueous stream containing 0.5 percentwt of crude FDCA composition. The crude FDCA composition consisted of 98.0 percentwt of FDCA, 1.0 percentwt of FFCA, and about 1.0 percentwt of the monomethyl ester of FDCA (FDCA-ME). The composition further contained some ppm of the components of the oxidation catalyst, viz. cobalt, manganese and bromine. Hydrogen-containing gas, consisting of 10 percentvol hydrogen and 90 percentvol nitrogen, was used for the hydrogenation. The catalysts used were Catalyst 1 , comprising 5 percentwt palladium on carbon and Catalyst 2, comprising 0.43 percentwt palladium on carbon. The experiments were conducted as follows. The reactor was charged with a desired load of the desired catalyst. The bed of catalyst was vented several times with hydrogen to remove any oxygen. Unless otherwise indicated, the reactor was subsequently pressurized with the hydrogen-containing gas to a pressure of 15 bar (at 20°C) and heated to the desired reaction temperature before the feedstock was passed over the bed of catalyst with the desired space velocity, expressed as weight hourly space velocity (WHSV) in grams of feedstock per gram of catalyst per hour. The Tables may also contain the contact time or residence time. EXAMPLE 1 In order to show the influence of the reaction temperature on the conversion of the FFCA to HMFA and MFA Catalysts 1 and 2 were used in experiments wherein the above feedstock was passed over beds of the two catalysts with different space velocities and at different reaction temperatures. From the reactor effluent the amounts of FFCA, HMFA and MFA were determined. The results are shown in Table 1. The amounts of FFCA, HMFA and MFA are expressed as mass percent, based on the amount of FFCA in the feedstock. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; In 1,4-dioxane; water; under 41254.1 Torr;Heating; Sealed tube; | [0192] 20 mg of different powder catalyst were placed into separate reaction vessels along with a solution containing 0.6 M FFCA in 3:2 (wt/wt) dioxaneiH^O. The powered catalysts were Cu BASF 0602 (reduced in-house), Cu Clariant T-4874, Cu Clariant T-4874* (reduced in-house), Ni JM HTC 500 RP, Pd/C JM-4, Pd/C JM-6, Pd/C JM-10, Pt/C JM-24, Pt/C JM-27, Ru/C JM-37, Ru/C JM-38 and a control without a catalyst. Catalysts Cu BASF 0602* and Cu Clariant T-4874* were used in a further reduced form (350°C in forming gas for 3 hours). Each reaction vessel was pressurized with hydrogen at target pressure of 55 bar. Reaction vessels were heated to a target temperature of 70°C and shaken for 2 hours or, alternatively, reaction vessels were heated to a target temperature of 100°C and shaken for 1 hour. After the reaction was completed, the shaking was stopped and the reactor was cooled down to room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; | To a solution of 5-methylfuran-2-carboxylic acid (1.0 g, 8.0 mmol, 1 equiv) and 2,6- dimethoxyaniline (1.46 g, 9.5 mmol, 1.2 equiv) in DCM (10 mL) were added DMAP (44 mg, 0.4 mmol, 0.05 equiv) and EDCI (1.5 g, 9.6 mmol, 1.2 equiv) successively at room temperature. The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (100 mL), washed with water (3*20 mL) and brine (50 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by flash column chromatography (eluted with PE/EtOAc = 20/1 ~ 1/1) to afford the title compound N-(2,6-dimethoxyphenyl)-5-methylfuran-2-carboxamide as a white solid (1.23 g, 59 % yield). LC-MS: m/z 262.1 (M+H)+ |
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