Structure of 3-Formylchromone
CAS No.: 17422-74-1
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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. : | 17422-74-1 |
Formula : | C10H6O3 |
M.W : | 174.15 |
SMILES Code : | O=CC1=COC2=CC=CC=C2C1=O |
MDL No. : | MFCD00014667 |
InChI Key : | FSMYWBQIMDSGQP-UHFFFAOYSA-N |
Pubchem ID : | 87112 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 47.87 |
TPSA ? Topological Polar Surface Area: Calculated from |
47.28 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.68 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.22 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.18 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.6 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.46 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.19 |
Solubility | 1.12 mg/ml ; 0.00643 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.81 |
Solubility | 2.7 mg/ml ; 0.0155 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.56 |
Solubility | 0.0484 mg/ml ; 0.000278 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) |
Yes |
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 |
-6.5 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 |
1.0 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) |
2.43 |
* 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 |
---|---|---|
37.6% | With triethylamine; In methanol; | In total, 1 mmol of <strong>[770-05-8]octopamine hydrochloride</strong>, 1 mmol triethylamine, and 1 mmol of chromone-3-carboxaldehyde were dissolved in 5 mL of MeOH. The reaction solution was stirred until white powder was formed, and the resulting powder was filtered and washed with acetone and ether. Yield: 116.3 mg (37.6%). 1H NMR (400 MHz in DMSO-d6, 20C): delta = 10.24 (s, 1H), delta = 9.30(s, 1H), delta = 7.77 (d, J = 8.1 Hz, 1H), delta = 7.44 (t,J = 8.2 Hz, 1H), delta = 7.31 (d, J = 12 Hz, 1H), delta = 7.18 (d,J = 8.2 Hz, 2H), delta = 7.05 (m, 2H), delta = 6.73 (d, J = 8 Hz,2H), delta = 5.63 (s, 1H), delta = 5.55 (t, J = 8 Hz, 1H), delta = 4.59(m, 1H), 3.46 (m, 1H). 13C NMR (700 MHz in DMSO-d6, 20 C, ppm): delta = 177.91, 156.51, 154.86, 133.18, 127.09,125.24, 123.16, 121.48, 117.52, 114.81, 101.52, 99.27,71.52, 56.22, 54.41. ESI-MS for C18H15NO4 + H+, Calcd,310.11 (m/z); found, 309.92. Elemental analysis Calcd (%)for C18H15NO4 + CH3OH: C, 66.85; H, 5.61; N, 4.10%;found (%): C, 66.69; H, 5.61; N, 3.99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 2h; | General procedure: To a mixture of carbaldehyde 3 (0.172 mmol, 1.0 equiv) and alkyne 4 (0.172 mmol, 1.0 equiv) in CH2Cl2 (2 mL) was added BF3·OEt2 (0.43 mmol, 2.5 equiv) at room temperature. The mixture was stirred for the required time (monitored by TLC). After completion of the reaction, it was quenched with a few drops of sat. Na2S2O3 solution. The solvent was removed through vacuum and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 4:1) to afford 6aa-6ah. |
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