Structure of 6100-60-3
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 6100-60-3 |
Formula : | C7H8O3 |
M.W : | 140.14 |
SMILES Code : | OC1=CC=C(OC)C(O)=C1 |
MDL No. : | MFCD00210443 |
Boiling Point : | No data available |
InChI Key : | GPJJASIJVRXZFI-UHFFFAOYSA-N |
Pubchem ID : | 3083936 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 36.98 |
TPSA ? Topological Polar Surface Area: Calculated from |
49.69 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.48 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.47 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.11 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.53 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.86 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.89 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.38 |
Solubility | 5.8 mg/ml ; 0.0414 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.08 |
Solubility | 11.6 mg/ml ; 0.0827 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.35 |
Solubility | 6.29 mg/ml ; 0.0449 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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.82 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 |
0.55 |
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) |
1.26 |
* 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 |
---|---|---|
95% | With hydrotacitile; In neat (no solvent); at 70℃; for 0.5h;Green chemistry; | General procedure: A mixture of phenols (0.0025 mol) and dicarbonyl (0.0025 mol) were heated at 70C under solvent free conditions using hydrotalcite (Mg-Al-CO3,50 mg) as a catalyst. The time taken by different phenols in reaction was as mentioned in Table 4. After completion of the reaction(TLC analysis using ethyl acetate:petroleum ether, 1:3), the reac-tion mixture was cooled to room temperature and poured in coldwater. The solid mass was filtered. It was dissolved in ethanol andfiltered. The solid hydrotalcite got separated as solid. The filtratehaving product soluble in ethanol was concentrate to crystallize theproduct. Hydrotalcite was washed with ethanol to remove organic impurity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
140 g | With methanol; potassium hydroxide; at 20℃; | The crude compound b was hydrolyzed in a mixture of MeOH (3 L) and 10% KOH (2 L) at RT over night. After MeOH was removed, the mixture was acidified by 6M HCl to PH=3 and extracted with DCM (2 L×8). The combined organic phase was washed with brine and dried on NaSO4. After the solvent was removed, the residue was purified by chromatography (EA:PE=6:1 to EA:PE=4:1) to give compound 3 (140 g, 50.5%) as light-yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The compounds of formula (VI) that are particularly preferred are chosen from: ... 2-methoxyresorcinol 5-methylpyrogallol 4-methoxyresorcinol 3,5-dihydroxytoluene monohydrate ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With boron trifluoride diethyl etherate; for 0.25h;Heating / reflux; | A mixture of 4-methoxyresorcinol (1.3 g, 9.29 mmol) and 4-hydroxyphenylacetic acid (1.27 g, 8.36 mmol) in BF3.Et2O (6.85 ml, 55.7 mmol) was heated at reflux temperature for 15 min under N2. After cooling to room temperature, the dark solution was poured into saturated aqueous sodium acetate (100 ml) and extracted with ethyl acetate (3×50 ml). The combined ethyl acetate layer was washed with 10% aq. NaHCO3 (50 ml) and water (100 ml), respectively, and dried with MgSO4. The solvent was evaporated under reduced pressure, and the dark brown oil was subjected to chromatography (CH2Cl2: EtOAc=8:2) to give the title compound as a yellow solid (1.1 g, 48%), mp 157-159 C. 1H NMR (300 MHz, DMSO-d6) delta 12.38 (s, 1H, OH), 10.48 (br s, 1H, OH), 9.29 (br s, 1H, OH), 7.40 (s, 1H, H-6), 7.08 (d, J=8.6 Hz, 2H, H-2', 6'), 6.69 (d, J=8.6 Hz, 2H, H-3', 5'), 6.30 (s, 1H, H-3), 4.16 (s, 2H, CH2), 3.76 (s, 1H, OCH3); 13C NMR (75 MHz, DMSO-d6) delta 202.2 (C-CO), 159.3 (C-4), 156.0 (C-4'), 155.4 (C-2), 141.0 (C-5), 130.4 (C-2',6'), 125.3 (C-1'), 115.6 (C-3',5'), 113.3 (C-6), 110.3 (C-1), 103.2 (C-2), 56.3 (C-OCH3), 43.6 (C-CH2). m/z=275 (M++1, 100%), 274 (16), 257 (9), 167 (18), 212; HRMS: C15H14O5 requires 274.9841 found 274.0829. |