Structure of 5355-17-9
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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. : | 5355-17-9 |
| Formula : | C8H10O2 |
| M.W : | 138.16 |
| SMILES Code : | OC1=CC=C(COC)C=C1 |
| English Name : | 4-(Methoxymethyl)phenol |
| MDL No. : | MFCD00020186 |
| InChI Key : | AHXXIALEMINDAW-UHFFFAOYSA-N |
| Pubchem ID : | 79310 |
| Num. heavy atoms | 10 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.25 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 39.32 |
| TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.62 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.16 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.39 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.21 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.67 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.41 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-1.74 |
| Solubility | 2.52 mg/ml ; 0.0182 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-1.37 |
| Solubility | 5.85 mg/ml ; 0.0423 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.33 |
| Solubility | 0.654 mg/ml ; 0.00473 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 |
-6.32 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) |
1.0 |
* 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 |
|---|---|---|
| 91% | at 20℃; for 2h; | |
| 91% | With ammonium cerium(IV) nitrate at 20℃; for 2h; | |
| 85% | With ytterbium(III) triflate In acetonitrile at 80℃; for 5h; |
| 80% | With hydrogenchloride; nitromethane In water at 30℃; for 5h; Inert atmosphere; | 1 Example 1 4-methoxymethylphenol Into a 100 mL three-necked flask equipped with a thermometer, a three-way cock, and a stirring bar, under a nitrogen stream, 3.96 g (0.03 mol) of 4-hydroxybenzyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 g of methanol (manufactured by Nacalai Tesque, Inc.), two drops of nitromethane (manufactured by Nacalai Tesque, Inc.) were added. While stirring at room temperature, 0.2 g of hydrochloric acid (manufactured by Nacalai Tesque, Inc.) was added dropwise, followed by stirring at 30 ° C. for 5 hours.The area percentage of HPLC at the end of the reaction was 95%. 0.28 g of pyridine (manufactured by Nacalai Tesque, Inc.) and 8 g of toluene (manufactured by Nacalai Tesque, Inc.) were added and neutralized, methanol was concentrated under reduced pressure, 31 g of toluene and 6 g of water were added to extract And the organic layer was washed with 5 g of water. The obtained organic layer was concentrated, cooled to 10 ° C. or less, and the precipitated crystals were filtered and dried to obtain 3.53 g (yield: 80%) of colorless 4-methoxymethylphenol. The HPLC purity was 99% (excluding solvent toluene). |
| 66% | With toluene-4-sulfonic acid for 6h; Ambient temperature; | |
| at 150℃; | ||
| With hydrogenchloride Heating; | ||
| 68.7 g | With hydrogenchloride In water for 1h; Ambient temperature; | |
| With hydrogenchloride | ||
| With sodium hydroxide for 4h; Heating; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In methanol |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sulfuric acid In methanol for 48h; Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With oxygen In methanol Irradiation; photozensitizer: eosin; | ||
| With oxygen In methanol Irradiation; photozensitizer; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92% | With sodium acetate for 3h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98% | With sulfuric acid for 4h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 72% | With potassium carbonate In methanol; water at 25℃; for 2h; other substrate: (3S,4S,5S,7aR)-(-)-3,5-bis(2-methoxyphenyl)-4-<(4-acetyloxyphenyl)methyl>pyrrolizidinium chloride; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 66% 2: 10% | With [bis(acetoxy)iodo]benzene at 20℃; for 4h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 4-hydroxybenzyl methyl ether With potassium <i>tert</i>-butylate In tetrahydrofuran at 25℃; for 1h; Stage #2: 3,5-dichloropyridine-4-carboxaldehyde In tetrahydrofuran at 70℃; for 2h; Further stages.; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium hydroxide; oxygen at 74.84℃; for 3h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | Stage #1: 4-hydroxybenzyl methyl ether With sodium hydride In tetrahydrofuran at 20℃; for 4h; Stage #2: ethyl chloromethyl ether In tetrahydrofuran at 20℃; Further stages.; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94% | With hydrogen bromide; dimethyl sulfoxide at 110℃; for 5h; | |
| 86.1% | 40 EXAMPLE 40 Conversion>99%. Yield: 86.1% of p-hydroxybenzaldehyde; 1.7% of p-hydroxybenzyl methyl ether. | |
| 85.3% | 39 EXAMPLE 39 Conversion>99%. Yield: 85.3% of p-hydroxybenzaldehyde; 2.6% of p-hydroxybenzyl methyl ether. |
| 70.4% | 38 EXAMPLE 38 Conversion>99%. Yield: 70.4% of p-hydroxybenzaldehyde; 0.5% of p-hydroxybenzyl methyl ether. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 4 h / 20 °C 1.2: 85 percent / tetrahydrofuran / 20 °C 2.1: Li; naphthalene / tetrahydrofuran / 2 h / -10 °C 2.2: 95 percent Spectr. / H2O / tetrahydrofuran / 0.5 h / -10 °C |

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