Structure of 28785-06-0
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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. : | 28785-06-0 |
Formula : | C10H12O |
M.W : | 148.20 |
SMILES Code : | O=CC1=CC=C(CCC)C=C1 |
MDL No. : | MFCD00041870 |
InChI Key : | MAUCRURSQMOFGV-UHFFFAOYSA-N |
Pubchem ID : | 120047 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.41 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.08 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.45 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.56 |
Solubility | 0.404 mg/ml ; 0.00272 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.55 |
Solubility | 0.422 mg/ml ; 0.00285 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.52 |
Solubility | 0.0446 mg/ml ; 0.000301 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 |
-5.4 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 |
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) |
1.0 |
* 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 |
---|---|---|
In pyridine; at 80℃; for 2h; | A 125 mL Ehrlenmayer flask equipped with a magnetic stirrer bar was charged with 7.76 g (47.8 mmol) of <strong>[28785-06-0]4-n-propylbenzaldehyde</strong>, 5.28 g (50.7 mmol) of malonic acid and 2.2 mL (2.2g, 27.2 mmol) of pyridine. The slurry was heated to 800C, at which temperature a clear yellow solution formed. After stirring for 2 hr, the reaction mixture was cooled to 25°C. The resulting solid was isolated by filtration, rinsing with water (2 X 30 mL) and 2: 1 methyl t-butyl ether (MTBE)/hexanes (2 X 30 mL). A total of 3.1 g of 4-n-Propylcinnamic acid was isolated.A 500 mL Parr shaker reaction vessel was charged with 3.10 g (15.2 mmol) of 4- n-Propylcinnamic acid, 20 mL of ethyl acetate and 10 mL of ethanol. This mixture was treated with 0.15 g of 10percent palladium on charcoal and placed under an atmosphere of 51 psig of hydrogen gas in a Parr shaker apparatus. A total of 14 psig of hydrogen was taken up in 16 hours. The reaction mixture was removed from the Parr shaker apparatus after dissipating the hydrogen gas, filtered through a Celite pad to remove the catalyst and concentrated to a white solid, 3-(4-n-Propylphenyl)propanoic acid (3.07 g). IH NMR <n="33"/>(d6-DMSO): delta 12.1, bs, IH (COOH); delta 7.09, d, 2H, (arylH's); delta 7.05, d, 2H (arylH's); delta 2.75, t, 2H, (CH2 beta to COOH); delta 2.47, m, 4H (CH2 alpha to COOH and CH2 alpha to aryl); delta 1.52, hex, 2H (CH2 beta to aryl); delta 0.85, t, 3H (CH3). 13C NMR (d6-DMS0): 173.76, 139.64, 138.01, 128.20, 128.02, 36.86, 35.28, 29.93, 24.11, 13.63. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 120℃; for 18h;Inert atmosphere; | General procedure: According to the method of Molander, et. al. (J. Org. Chem. 2009, 74, 3636), a suspension of 5-bromo-2-formylfuran (695 mg, 3.97 mmol), hexylboronic acid (775 mg, 5.96 mmol), potassium carbonate ( 1.65 g, 11.91 mmol), palladium(II) acetate (18 mg, 0.079 mmol) and RuPhos (74 mg, 0.16 mmol) in 9: 1 toluene/water (22 mL) in a pressure-relief vial under argon was heated in a 120 °C bath for 18 h. After cooling to room temperature, the tion mixture was diluted with water (25 mL) and organics extracted with ether (3 x 50 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel (10percent ethyl acetate in hexanes) to give 5-hexyl-2-formylfuran (665 mg, 93percent) as a clear oil. Used without further characterization. |
According to the procedure of example 1a, upon substituting in place of the benzaldehyde, one of the following substituted benzaldehydes:...m-chlorobenzaldehydep-trifluoromethylbenzaldehydem-fluorobenzaldehydeo-methylbenzaldehydep-propylbenzaldehydem-ethoxybenzaldehydep-propoxybenzaldehyde | ||
With bis(trichloromethyl) carbonate; 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine; triethylamine; In dichloromethane; at -30℃; for 1h;Inert atmosphere; | General procedure: (1) To a 50 mL two-necked flask, 1.24 g (1.5 eq, 4.17 mmol) of 4- (2- (2- (methylsulfoxy) ethyl) -4-nitrophenyl) morpholine was added, Methyl chloride, magnetic stirring nitrogen protection, ice salt bath cooling to -30 ,A solution of 0.41 g (0.5 eq, 1.39 mmol) of bis (trichloromethyl) carbonate in 3 mL of anhydrous methylene chloride was added dropwise, stirring was continued for 0.5 h, and 0.3 g (2.78 mmol) of benzyl alcohol in 3 mL of anhydrous dichloromethane (3.0 eq, 8.34 mmol) of triethylamine was added dropwise. The reaction was complete by TLC. The mixture was stirred for 0.5 hours. The organic layer was separated and the dichloromethane was recovered under reduced pressure. The residue was added hydrochloric acid solution adjusted to pH 3, petroleum ether extraction separation, the organic layer vacuum recovery of petroleum ether 0.28g benzaldehyde, yield 94.9percent.(2) the aqueous layer of ice water bath drop sodium hydroxide solution adjusted to pH 10, dichloromethane extraction separation, organic layer vacuum recovery of methylene chloride was 0.95g by-product sulfide (VI) and excessive new sub- Sulfone (I). The structure of the by-product thioether (VI) was confirmed |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In ethanol; for 24h; | EXAMPLE 5 Bis-1,3,2,4-(4'-propylbenzylidene)-1-Propyl Sorbitol A one liter reaction kettle, equipped with a stirrer and nitrogen inlet, was charged with the propyl sorbitol ethanol solution. 40 g (0.27 mol) of <strong>[28785-06-0]4-propylbenzaldehyde</strong>, and 2.6 g of p-toulenesulfonic acid monohydrate was added to the reaction vessel. The clear solution was stirred for 24 hours, during which time a significant amount of white precipitate formed. The white powder was isolated by filtration and washed with 250 ml of 1 M NaOH aqueous solution. The white powder was suspended in water and further neutralized to pH=7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7*500 ml of boiling water. The washed powder dried overnight. The white powder was then stirred in 500 mL of cyclohexane, heated until boiling, filtered, and washed with 2*250 ml of boiling cyclohexane. Further purification was accomplished by using an Ace Glass 6810 Giant Soxhlet Extraction Apparatus (size F) and cellulose fiber thimble (58*170 MM OD) with 2000 ml of methanol. The white powder was slurried in 250 ml of methanol, poured into the thimble, and extracted over 5 days of reflux. The resultant extract was chilled to 5° C. and filtered to collect the white solid, which was slurried in 1000 ml of petroleum ether, filtered, and air dried. The isolated white powder was dried in a vacuum oven to give 20.1 g of product, m.p. 244-245° C. The purity was above 99percent, based on GC-MS. 1H NMR(500 MHz, DMSO-d6, ppm): 0.86-0.89 (m, 6H, Ph-CH2CH2CH3), 0.91-0.94 (t, 3H, sugar-CH2CH2CH3), 1.35-1.49 (m, 2H, sugar-CH2CH2CH3) 1.54-1.60 (m, 4H, Ph-CH2CH2CH3), 1.61-1.71 (m, 2H, sugar-CH2CH2CH3), 2.53-2.56 (t, 4H, Ph-CH2CH2CH3), 3.41-4.04 (m, 7H, sugar H), 4.36-4.39 (t, 1H, -CH2OH), 4.78-4.79 (d, 1H, -CHOH), 5.60 (s, 1H, acetal), 5.62 (s, 1H, acetal), 7.17-7.20 (dd, 4H), 7.32-7.37 (dd, 4H). |
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