Structure of 59032-71-2
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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. : | 59032-71-2 |
Formula : | C11H18O3 |
M.W : | 198.26 |
SMILES Code : | O=C(C1(CC)CCC(CC1)=O)OCC |
MDL No. : | N/A |
InChI Key : | DHQTYJFKOHBZOM-UHFFFAOYSA-N |
Pubchem ID : | 21911982 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.82 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 54.1 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.34 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.34 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.09 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.49 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.66 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.98 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.65 |
Solubility | 4.44 mg/ml ; 0.0224 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.85 |
Solubility | 2.78 mg/ml ; 0.014 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.7 |
Solubility | 0.394 mg/ml ; 0.00199 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 |
-6.56 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 |
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) |
2.09 |
* 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 |
---|---|---|
99% | With hydrogenchloride; water; In acetone; at 20℃; for 16h; | To a stirred solution of compound D22-1 (2.07 g, 8.54 mmol) in acetone (60 mL) was added aqueous HC1 (2 M solution, 40 mL) at room temperature. The mixture was stirred at the same temperature for 16 h. Acetone was removed under reduced pressure. The residue was basified with aqueous NaHC03 solution and extracted with DCM (2 x 30 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over Na2S04 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to give compound D22-2 (1.85 g, 99%) as a colorless gum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate; In methanol; at 0℃; for 0.583333h; | [0464] To a solution of 1.65 g of <strong>[59032-71-2]ethyl 1-ethyl-4-oxocyclohexanecarboxylate</strong> (which was prepared by the method as described in J. Am. Chem. Soc.,1979, 101, 6414-6420) in 17 ml of methanol, 250 mg of sodium borohydide was added at 0 C., followed by 35 minutes' stirring at the same temperature. After adding water to the reaction liquid, the solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried on anhydrous magnesium sulfate, and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (ethyl acetate/hexane=1/3) to provide 648 mg of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Dissolve tert-butyi 4-amino-4-(arninomethyl)piperidine- 1 -carboxylate (1.4 g, 5.7 mmol), ethyl I -ethyi-4-oxo-cyclohexanecarboxy]ate (1.4, 5.7 mmo]) and acetic acid (0.3 mL, 5,7 mmol) in DCM (5.7 mL) at it After 30 mm, add sodium triacetoxyborohydride (1.6 g, 7.5 mmol) and stir the mixture at rt for 18 hrs. Dilute the mixture with DCM (2()() rnL), and wash with saturated aqueous solution of NaHCO3 (100 mL). Dry the organic phase over Na2SO4 filter, and remove the solvent from the filtrate to give the title compound as a brown oil in quantitative yield (mixture of cis/trans isomers). This material can be used in the next step without any thrther purification. ES/MS rn/z 412 (M-t-H). |
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