Structure of 702-98-7
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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. : | 702-98-7 |
Formula : | C11H18O |
M.W : | 166.26 |
SMILES Code : | OC1(C)C2CC3CC(C2)CC1C3 |
MDL No. : | MFCD00074811 |
InChI Key : | JKOZWMQUOWYZAB-UHFFFAOYSA-N |
Pubchem ID : | 136545 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 49.85 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.33 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.74 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.31 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.2 |
Solubility | 1.05 mg/ml ; 0.00631 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.17 |
Solubility | 1.14 mg/ml ; 0.00683 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.52 |
Solubility | 5.02 mg/ml ; 0.0302 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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.82 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 |
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) |
3.91 |
* 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 |
---|---|---|
80% | With triethylamine; In tetrahydrofuran; diethyl ether; | b. Synthesis of 2-methyl-2-adamantyl acrylate 2-methyl-2-adamantanol (33 g, 0.2 mol) and triethylamine (0.22 mol) were dissolved in 300 ml of THF and then acryloyl chloride (19g, 0.21 mol) was added slowly thereto using a dropping funnel. Then, the reaction was stirred at room temperature for about 12 hours. After completion of the reaction, excess THF was removed using a rotary evaporator and then the resultant product was poured into water. Then, the resultant product was neutralized with dilute sulfuric acid and extracted using diethyl ether and was then dried over magnesium sulfate. The diethyl ether removed crude product was vacuum-distilled to yield the desired product (yield: 80%). |
80% | With triethylamine; In tetrahydrofuran; diethyl ether; | b. Synthesis of 2-methyl-2-adamantyl acrylate 2-methyl-2-adamantanol (33 g, 0.2 mol) and triethylamine (0.22 mol) were dissolved in 300 ml of THF and then acryloyl chloride (19 g, 0.21 mol) was added slowly thereto using a dropping funnel. Then, the reaction was stirred at room temperature for about 12 hours. After completion of the reaction, excess THF was removed using a rotary evaporator and then the resultant product was poured into water. Then, the resultant product was neutralized with dilute sulfuric acid and extracted using diethyl ether and was then dried over magnesium sulfate. The diethyl ether removed crude product was vacuum-distilled to yield the desired product (yield: 80%). 1H-NMR (CDCl3; ppm): 6.3 (doublet), 6.1 (1H, dd), 5.7 (1H, d), 2.3 (2H, s), 1.5-2.1 (m) FT-IR (NaCl; cm-1): 2911, 2861, 1718, 1635, 1618, 1401, 1201 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.31 parts of the salt represented by formula (I-1-a) and 20 parts of acetonitrile are mixed,The mixture was stirred at 23 C for 30 minutes. 1.80 parts of carbonyldiimidazole was added to the obtained mixed solution, and the mixture was stirred at 60 C. for 2 hours. 2.00 parts of the compound represented by the formula (I-231-b) was added to the obtained reaction solution, the mixture was stirred at 60 C. for 2 hours, and then cooled to 23 C. Chloroform (40 parts) and ion-exchanged water (20 parts) were added to the obtained reaction mixture, and the mixture was stirred at 23 C. for 30 minutes, then, separated, and the organic layer was taken out. 20 parts of ion-exchanged water was added to the obtained organic layer, the mixture was stirred at 23 C. for 30 minutes, and then liquid-separated to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, and the concentrated mixture was applied to a column (silica gel 60N (spherical, neutral) 100-210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: n-heptane / ethyl acetate = 1/1). By fractionating, 2.56 parts of a compound represented by the formula (I-231-c) was obtained. |
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