Structure of 2675-79-8
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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. : | 2675-79-8 |
Formula : | C9H11BrO3 |
M.W : | 247.09 |
SMILES Code : | C1=C(C(=C(C=C1Br)OC)OC)OC |
MDL No. : | MFCD00017169 |
InChI Key : | XAOOZMATJDXDQJ-UHFFFAOYSA-N |
Pubchem ID : | 75885 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H317 |
Precautionary Statements: | P261-P280 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.62 |
TPSA ? Topological Polar Surface Area: Calculated from |
27.69 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.68 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.62 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.9 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.51 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.44 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.17 |
Solubility | 0.169 mg/ml ; 0.000682 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.85 |
Solubility | 0.348 mg/ml ; 0.00141 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.64 |
Solubility | 0.0569 mg/ml ; 0.00023 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 |
-5.95 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.05 |
* 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 |
---|---|---|
71% | 5-Bromo-1,2,3-trimethoxybenzene (1.60 g, 6.47 mmol) was dissolved in THF (50 mL) and cooled to -78 C. n-BuLi (2.7 mL, 6.8 mmol) was added dropwise, and the reaction mixture was stirred for 1 h. Ketone 11 (0.92 g, 4.79 mmol) was dissolved in THF (10 mL) and added dropwise to the reaction flask, and the mixture was stirred for 12 h while warming to room temperature, at which time it was washed with water, extracted with EtOAc (3*30 mL), dried over sodium sulfate, concentrated, and purified by flash chromatography using a prepacked 50 g silica column [solvent A: EtOAc; solvent B: hexane; gradient: 10% A/90% B (1 CV), 10% A/90% B?80% A/20% B (10 CV), 80% A/20% B (1 CV); flow rate: 50 mL/min; monitored at 254 nm and 280 nm] to afford tertiary alcohol 25 (1.221 g, 3.39 mmol, 71%) as an orange oil. NMR data was collected after the subsequent step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.9% | With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 100 - 108℃; for 8h;Inert atmosphere; | The reaction route is as follows:250mL three-necked flask was added 2.71g (0.01mol)1,1-bis (4-aminophenyl) cyclohexane,11.31 g (0.046 mol) of 3,4,5-trimethoxybenzene,5.71 g (0.051 mol) potassium t-butoxide,54.2 g toluene.Under nitrogen atmosphere, 0.373 g (4.1 10-4 mol) of Pd2 (dba) 3,0.236 g (8.1 × 10 -4 mol) (t-Bu) 3PH · BF 4,The temperature was raised to 100 C to 108 C and refluxed for 8 hours.Completed the reaction,Add 50g water twice,Dried over anhydrous sodium sulfate,Decompression solvent was brown viscous liquid.The above crude product was treated with THF,Ethyl acetate (mass ratio of 5: 5) recrystallization,6.8g white powder was obtained,Yield: 71.9%. |
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