Structure of 4-Methyl-1-tetralone
CAS No.: 19832-98-5
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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. : | 19832-98-5 |
| Formula : | C11H12O |
| M.W : | 160.21 |
| SMILES Code : | O=C1CCC(C)C2=C1C=CC=C2 |
| MDL No. : | MFCD00001691 |
| InChI Key : | SRLHDEROUKFEMJ-UHFFFAOYSA-N |
| Pubchem ID : | 89232 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 12 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.36 |
| Num. rotatable bonds | 0 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 49.1 |
| TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.05 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.35 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.77 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.3 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.08 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.51 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.68 |
| Solubility | 0.332 mg/ml ; 0.00207 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-2.35 |
| Solubility | 0.719 mg/ml ; 0.00448 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.54 |
| Solubility | 0.0462 mg/ml ; 0.000288 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 |
-5.61 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) |
2.03 |
* 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 |
|---|---|---|
| To a stirred solution of commercially available 4-methyl-alpha-tetralone (0.50 g, 3.12 mmol) in methanol (50 mL) was added NaBH4 (0.35 g, 9.36 mmol) portionwise. The reaction mixture was followed by TLC and, after complete consumption of the starting material (approx. 2 h), was quenched with saturated NaHCO3. The aqueous layer was extracted with diethyl ether, dried with magnesium sulfate (MgSO4), filtered, and the solvent was removed under reduced pressure. The crude alcohol was dissolved in toluene (15 mL), and a few crystals of p-TsOH were added. The reaction mixture was stirred overnight, then neutralized by slow addition of saturated sodium bicarbonate (NaHCO3) and extracted with diethyl ether. The combined organic layers where washed with brine, dried with magnesium sulfate (MgSO4), filtered, and the solvent was removed under reduced pressure. The product was purified by flash chromatography (SiO2, hexanes) to give 1,2-dihydro-1-methylnaphthalene ((+/-)-8) as a clear oil (0.35 g, 78% yield). The compound is volatile and cannot be dried for long periods (>30 min) under high vacuum. The spectroscopic data are consistent with previously reported data (Ferraz, which is hereby incorporated by reference). |
[ 19832-98-5 ]
[ 540-63-6 ]
[ 19832-98-5 ]
[ 105-36-2 ]
[ 19832-98-5 ]
[ 535-11-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 77% | With Oxone; ammonium bromide; In methanol; for 2h;Reflux; | General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3×25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data. |
| With bromine; In ethyl acetate; | (a) 4.8 g (0.03 mole) of 4-methyl-1-tetralone are reacted with 4.8 g (0.03 mole) of bromine in ethyl acetate, analogously to the instructions indicated in Example 29 (a), to give 2-bromo-4-methyl-1-tetralone. The oily product is further processed immediately without further purification. |

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