Structure of 54344-92-2
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 54344-92-2 |
Formula : | C11H14O2 |
M.W : | 178.23 |
SMILES Code : | COC1=C(C)C(C)=C(C=O)C(C)=C1 |
MDL No. : | MFCD00456729 |
Boiling Point : | No data available |
InChI Key : | BTOFIDLWQJCUJG-UHFFFAOYSA-N |
Pubchem ID : | 824142 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.36 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.22 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.28 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.45 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.43 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.42 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.7 |
Solubility | 0.357 mg/ml ; 0.002 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.65 |
Solubility | 0.403 mg/ml ; 0.00226 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.63 |
Solubility | 0.0415 mg/ml ; 0.000233 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 |
-5.65 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) |
1.3 |
* 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 potassium hydroxide; sodium acetate; trichlorophosphate; In N-methyl-acetamide; ethanol; water; benzene; | EXAMPLE 1 The following procedure is illustrative of the synthesis of compounds represented by formula I. A total of 500 g of 2,3,5-trimethylphenol were introduced into 1840 ml of ethanol and 184 ml of water and treated with 240 g of potassium hydroxide with gentle stirring. 626 Grams of methyl iodide were added to the resulting clear solution at 0-5 over a period of 30-45 minutes. The mixture was stirred for 2 hours at room temperature, subsequently stirred under reflex conditions at 60 for 12 hours, then treated with 5 liters of water and thoroughly extracted with a total of 6 liters of ether. The extract was washed first with 3 liters of 3-N sodium hydroxide, then twice with 1 liter portions of water, dried over sodium sulfate and evaporated under reduced pressure. The residual <strong>[20469-61-8]<strong>[20469-61-8]2,3,5-trimethylanisol</strong>e</strong> boiled at 88-90 /10 Torr after rectification. 184 Grams of phosphorus oxychloride were added dropwise over 20-30 minutes to 87.1 g of dimethylformamide while at 10-20 with stirring. As the addition neared completion the temperature rose to 25. 150 Grams of <strong>[20469-61-8]<strong>[20469-61-8]2,3,5-trimethylanisol</strong>e</strong> were added over 20 minutes while cooling at 10-20. The mixture was slowly heated up to a maximum of 115, stirred at 100 for 6 hours in order to complete the reaction, cooled, poured into 2 kg of ice/water (1:1) and, after the addition of 1500 ml of benzene, treated with 500 g of sodium acetate. The water phase which formed was separated after stirring for 1 hour and again extracted with 1000 ml of benzene. The combined benzene extracts were washed successively with 480 ml of 1.5-N hydrochloric acid and 500 ml of water, dried over sodium sulfate and filtered over 20 g of decolorizing carbon. The filtrate was evaporated under reduced pressure. The residual 2,3,6-trimethyl-p-anisaldehyde melted at 65-66 after recrystallization from hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49%Chromat. | With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; bis(cyclooctadiene)iridium(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; In tetrahydrofuran; at 135℃; for 24h;Sealed tube; Inert atmosphere; | General procedure: An oven-dried sealed tube was charged with [Ir(cod)2](BArF4)(0.0125 mmol, 5 mol%), (R)-Xyl-BINAP (0.0138 mmol, 5.5 mol%),and anhyd THF (1.0 mL) under N2, and the mixture was stirredat r.t. for 30 min. 2-(Phenoxymethyl)benzaldehyde (1b; 0.25mmol) was added and the resultant mixture was heated at 135 Cfor 24 h with stirring. The mixture was then purified by columnchromatography (silica gel, hexane) to give a colorless liquid;yield: 16.1 mg (35%). |
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