Structure of 7500-37-0
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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. : | 7500-37-0 |
Formula : | C10H9BrO3 |
M.W : | 257.08 |
SMILES Code : | CC(OCC(C1=CC=C(Br)C=C1)=O)=O |
MDL No. : | MFCD00174274 |
Boiling Point : | No data available |
InChI Key : | DYDDLQHJYMWTMU-UHFFFAOYSA-N |
Pubchem ID : | 343879 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 55.24 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.23 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.22 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.62 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.89 |
Solubility | 0.335 mg/ml ; 0.0013 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.77 |
Solubility | 0.441 mg/ml ; 0.00172 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.68 |
Solubility | 0.0533 mg/ml ; 0.000207 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) |
Yes |
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 |
-6.29 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 |
0.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.62 |
* 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 |
---|---|---|
82% | With PEG2(at)SiO2(at)Fe3O4; In water; for 1.25h;Reflux; | General procedure: A magnetically stirred solution of alpha-bromo ketone (1.0 mmol) andNaX (2.0 mmol) in water (5.0 mL), PEGSiO2Fe3O4 (50 mg) was added. The resulting suspension was stirred under reflux conditions for the time shown in Table 1. After completion of the reaction that confirmed by TLC, the MNPs were removed magnetically and solid was filtered off, washed with water and subjected to flash chromatography.The desired phenacyl derivatives obtained in 82% to 94% isolated yields. |
74% | With 1,4-bis(imidazol-1-yl)butane-based poly(ionic liquid); In water; at 60℃; for 0.25h;Green chemistry; | General procedure: A magnetically stirred mixture of alpha-bromo ketone (1.0 mmol) with NaY (1.5 mmol) and the catalyst 3(0.01 g) in water (5 mL) was heated to 60C for the time specified in the table. Progress of the reaction was monitored by TLC. After completion of the reaction,diethyl ether (3×5 mL) was added and the obtained organic phase was separated and dried with CaCl2. The solvent was removed in vacuo. The residue formed was purified by column chromatography on silica gel to give the corresponding phenacyl derivatives. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.2% | With triethylamine; In acetonitrile; at 80℃; for 2h; | 4-(Bromoacetyl)bromobenzene (6.00 g, 21.6 mmol, 1 equiv),Acetonitrile (50 mL), triethylamine (6.0 mL, 43.2 mmol, 2 equiv),Acetic acid (2.5 mL, 43.2 mmol, 2 equiv) was placed in a 100 mL eggplant bottle in turn.The temperature was raised to 80 C for 2 hours. After the reaction was completed, the solvent was evaporated, and the residue was dissolved in dichloromethane (100 mL).Wash the organic layer with 2N hydrochloric acid (100 mL), and wash several layers with saturated aqueous sodium carbonate (100 mL).The organic layer was washed with distilled water, dried over anhydrous sodium sulfate, evaporated and evaporated5.01 g of a yellow solid was obtained in a yield of 90.2%. |
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