Structure of 2142-76-9
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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. : | 2142-76-9 |
Formula : | C10H12O |
M.W : | 148.20 |
SMILES Code : | CC(=O)C1=C(C)C=CC=C1C |
MDL No. : | MFCD01861394 |
Boiling Point : | No data available |
InChI Key : | DDXBCZCBZGPSHD-UHFFFAOYSA-N |
Pubchem ID : | 16506 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.57 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.06 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.33 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.51 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.11 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.48 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.56 |
Solubility | 0.404 mg/ml ; 0.00273 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.33 |
Solubility | 0.697 mg/ml ; 0.0047 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.49 |
Solubility | 0.0483 mg/ml ; 0.000326 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 |
-5.55 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 |
2.0 |
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) |
1.0 |
* 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 |
---|---|---|
57% | With indium In neat (no solvent) at 20℃; for 8 h; Inert atmosphere; Sonication | General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water–detergent bath at 60 °C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70percent; output power = 70percent) for 10 min. After addition of 10percent (m/v) solution of No.18 NaOH (2 mL) and 10 μL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90percent recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 Å, 70–230 mesh) doped with 10percent of KF (hexanes/DCM 8:2) gave 0.096 g (53percent) of 3fa as a colorless oil. |
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