Structure of 4903-09-7
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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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CAS No. : | 4903-09-7 |
Formula : | C8H7ClO2 |
M.W : | 170.59 |
SMILES Code : | COC1=C(Cl)C=C(C=O)C=C1 |
MDL No. : | MFCD00016601 |
InChI Key : | WYVGYYIZXPXHAZ-UHFFFAOYSA-N |
Pubchem ID : | 78619 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 43.33 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.99 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.16 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.71 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.61 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.05 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.42 |
Solubility | 0.644 mg/ml ; 0.00378 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.17 |
Solubility | 1.16 mg/ml ; 0.00678 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.08 |
Solubility | 0.141 mg/ml ; 0.000824 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 |
-5.93 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 |
1.0 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) |
1.21 |
* 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 sodium borohydrid; In tetrahydrofuran; ethanol; | PREPARATION 44 To a solution of <strong>[4903-09-7]3-chloro-4-methoxybenzaldehyde</strong> (156 g) in a mixture of ethanol (750 ml) and tetrahydrofuran (500 ml) was added sodium borohydride (25 g) under ice-cooling. After stirring at ambient temperature for 2 hours, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, 1N-hydrochloric acid, water, aqueous sodium bicarbonate and brine, successively, and dried over magnesium sulfate. Evaporation of the solvent gave 3-chloro-4-methoxybenzyl alcohol (164 g) as a yellow oil. NMR(CDCl3, delta): 1.70 (1H, t, J=7 Hz), 3.90 (3H, s), 4.60 (2H, d, J=7 Hz), 6.90 (1H, d, J=8 Hz), 7.22 (1H, dd, J=4 Hz, 8 Hz), 7.39 (1H, d, J=4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With ammonium persulfate; N-chloro-succinimide; oxygen; methylene green; In acetonitrile; at 20℃; for 24h;Irradiation; | General procedure: To an oven-dried flask was added a magnetic stir bar, methylene green (9.1 mg, 0.05 equiv, 0.025 mmol), ammonium peroxodisulfate (11.4 mg, 0.1 equiv, 0.05 mmol), arene/heteroarene (1 equiv, 0.5 mmol), acetonitrile (2.5 mL), and then N-chlorosuccinimide (73.4 mg, 1.1 equiv, 0.55 mmol). The reaction mixture was stirred open to air at room temperature (20 C) in a white LED chamber for 24 h. For substrates that produced a mixture of mono- and dibrominated products upon full conversion, 2.2 equivalents (1.1 mmol) of N-chlorosuccinimide was employed. Upon completion of the reaction, the crude mixture was evaporated under pressure and the chlorinated product was isolated via column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium hydroxide; In dimethyl sulfoxide; at 40℃; for 7h;Inert atmosphere; | To a mixture of <strong>[4903-09-7]3-chloro-4-methoxybenzaldehyde</strong> (2.00 g,11.7 mmol) and trimethylsulfonium iodide (3.35 g, 16.4 mmol) inDMSO (12 mL) was added potassium hydroxide (0.920 g,16.4 mmol). After stirring at 40 C for 7 h, the reaction mixturewas diluted with EtOAc (50 mL) and washed with H2O (100 mL).The aqueous layer was extracted with EtOAc (50 mL). To the combinedorganic layer was added toluene (100 mL), and the wholewas washed with H2O (100 mL), dried over Na2SO4, filtered andconcentrated in vacuo to give 2.25 g (quant.) of the title compoundas a pale yellow oil. The obtained compound 12a was used in thenext reaction without further purification. 1H NMR (300 MHz,CDCl3) d: 2.77 (1H, dd, J = 5.3, 2.6 Hz), 3.13 (1H, dd, J = 5.3,4.0 Hz), 3.80 (1H, dd, J = 4.0, 2.6 Hz), 3.90 (3H, s), 6.90 (1H, d,J = 8.4 Hz), 7.16 (1H, dd, J = 8.5, 2.1 Hz), 7.28 (1H, d, J = 2.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
wherein the compound of Formula I is selected from the group consisting of...4-acetoxy-3,5-dimethoxybenzaldehyde;3,4-dimethoxybenzaldehyde;2-carboxyl-3,4-dimethoxybenzaldehyde;2,4,5-trimethoxybenzaldehyde;3-chloro-4-methoxybenzaldehyde;3-butyloxy-4-methoxybenzaldehyde;3,5-dimethoxy-4-benzoxybenzaldehyde;3,5-dichloro-4-methoxybenzaldehyde;... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogenchloride; sodium hydroxide; | Preparation 88 Synthesis of (E)-1-(3-bromo-2-hydroxy-5-methylphenyl)-3-(3-chloro-4-methoxyphenyl)-2-propen-1-one 1-(3-Bromo-2-hydroxy-5-methylphenyl)-1-ethanone (10 g, 43.7 mmol) and <strong>[4903-09-7]3-chloro-4-methoxybenzaldehyde</strong> (9.0 g, 1.2 molar eq.) were introduced into 80percent aqueous ethanol solution (150 ml), sodium hydroxide (NaOH; 5.2 g, 3.0 molar eq.) was added thereto, and the resulting mixture was stirred for 17 hours at room temperature. After completion of reaction, the reaction solution was neutralized by 2N aqueous hydrochloric acid solution and diluted with water (150 ml). The yellow solid thus precipitated was washed with water and methanol to give 14.2 g (Yield 85percent) of the purified title compound. 1H NMR (CDCl3, ppm) 7.88 (1H, d), 7.78 (1H, s), 7.68 (1H, s), 7.63 (1H, s), 7.54 (2H, m), 6.87 (1H, d), 3.98 (3H, s), 2.37 (3H, s). Mass (m/e)=381[M++1]+ |
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