Structure of TBMP
CAS No.: 88-32-4
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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.
Synonyms: 3-tert-Butyl-4-methoxyphenol
4.5
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| CAS No. : | 88-32-4 |
| Formula : | C11H16O2 |
| M.W : | 180.24 |
| SMILES Code : | COC1=C(C=C(O)C=C1)C(C)(C)C |
| Synonyms : |
3-tert-Butyl-4-methoxyphenol
|
| English Name : | 3-(tert-Butyl)-4-methoxyphenol |
| MDL No. : | MFCD00057667 |
| InChI Key : | IMOYOUMVYICGCA-UHFFFAOYSA-N |
| Pubchem ID : | 6932 |
| Num. heavy atoms | 13 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.45 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 54.23 |
| TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.3 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.21 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.7 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.39 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.53 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.63 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-3.19 |
| Solubility | 0.117 mg/ml ; 0.000647 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.5 |
| Solubility | 0.0569 mg/ml ; 0.000316 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.16 |
| Solubility | 0.125 mg/ml ; 0.000693 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 |
-5.12 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) |
1.24 |
* 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 |
|---|---|---|
| With hydrogenchloride; mercaptoacetic acid; calcium chloride Reagens 4: Benzol; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 260℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 260℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With nitric acid; acetic acid Hydrieren des Reaktionsprodukts an Raney-Nickel in Dioxan; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hexane; phosphoric acid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With aluminum oxide; silica gel at 170℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride; mercaptoacetic acid; calcium chloride Reagens 4: Benzol; | ||
| With hydrogenchloride; mercaptoacetic acid; calcium chloride Reagens 4: Benzol; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 70% | With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 120℃; for 17h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92% | With potassium dihydrogenphosphate; potassiuim nitrosodisulfonate In water; acetone |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 46 mg | With 2,4,6-trimethyl-pyridine; copper(I) oxide; potassium carbonate for 48h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 0.13 g | In hexane; dichloromethane for 4h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 40 mg | With sodium hydroxide; potassium hexacyanoferrate(III) In dichloromethane for 0.00277778h; Yields of byproduct given; | |
| 40 mg | With sodium hydroxide; potassium hexacyanoferrate(III) In dichloromethane for 0.00277778h; Yield given; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With silver(l) oxide In tetrachloromethane |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride In tetrahydrofuran | ||
| 98 % | With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | 1 Preparation of 2-tert-butyl-4-hydroxyanisole: Weigh tert-butyl (3-(tert-butyl)-4-methoxyphenoxy)dimethylsilane (0.6g, 2mmol), dissolve it in tetrahydrofuran (5mL) and add it to the reaction bottle.At the same time, tetrabutylammonium fluoride (TBAF) dissolved in tetrahydrofuran (1M, 4ml, 4mmol) was added to the reaction bottle, and the reaction was stirred at room temperature for 1 hour. After the reaction, the reaction solution was quenched with saturated ammonium chloride (50 mL), extracted three times with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by column chromatography to obtain 2-tert-butyl-4-hydroxyanisole (yield 98%, purity 95%). |

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