Structure of 1754-55-8
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 1754-55-8 |
Formula : | C12H16O2 |
M.W : | 192.25 |
SMILES Code : | CCOC(=O)C1=C(C)C=C(C)C=C1C |
MDL No. : | MFCD00015439 |
InChI Key : | ZXTXIZPSMQCYBN-UHFFFAOYSA-N |
Pubchem ID : | 74465 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.42 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 57.43 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.76 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.23 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.79 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.13 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.52 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.19 |
Solubility | 0.125 mg/ml ; 0.000652 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.46 |
Solubility | 0.0674 mg/ml ; 0.000351 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.04 |
Solubility | 0.0174 mg/ml ; 0.0000906 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
No |
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 |
-5.18 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) |
1.78 |
* 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 N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4.0h;Reflux; | Ethyl 2,4,6-trimethylbenzene (4.20 g, 21.41 mmol) and Lambda/-bromosuccinimide (4.23 g, 23.55 mmol) are taken up in carbon tetrachloride (200 mL), and benzoyl peroxide (0.53 g, 2.14 mmol) is added. The suspension is heated to reflux. After 4 h, the mixture is diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, water and brine, dried and concentrated in vacuo. The residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 1 to 5%) to give partially purified 4- <n="88"/>bromomethyl-2,6-dimethyl-benzoic acid ethyl ester, which is taken in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With naphthalene; phosphorus; sodium; tert-butyl alcohol; In 1,2-dimethoxyethane; at 60℃; for 16.0h; | Red phosphorous (P4, 0.248 g, 2 mmol) and naphthalene (0.104 g, 0.8 mmol, 0.1 eq.) were suspended in 10 ml dme. Freshly cut sodium pieces (Na, 0.552 g, 24 mmol, 3 eq.) were subsequently added to the suspension. The mixture was stirred for 12 hours, then tBuOH (1.61 ml, 16 mmol, 2 eq.) in 5 ml dme was added dropwise to the mixture at 0 C. The resulting black suspension was stirred for an additional 2 hours. Subsequently, mesityl(ethylcarboxylate) (1.78 mL, 8.8 mmol, 1.1 eq.) was added and reacted at 60 C for 16 h to give Na[HP-CO(Mes)]. To this yellow suspension, HCl (2M in diethyl ether, 12 mL, 24 mmol, 3 eq.) was added dropwise at 0 C and the reaction mixture was stirred for 30 min.. Subsequently, the solvent and all volatiles were removed under reduced pressure. The residue was again dissolved in dme (10 ml) and 2-(2-ethoxyethoxy) ethyl acrylate (3.0 ml, 16 mmol, 2 eq.) and l,5-diazabicyclo-[4,3,0]-non-5-ene (DBN, 0.1 ml, 0.8 mmol, 10%) were added at 0 C. The mixture was warmed to room temp, and stirred for 1 h. Then HCl (2M in Diethyl ether, 0.4 mL, 0.8 mmol, 0.1 eq.) was added dropwise at 0 C and the mixture stirred for 30 min before dme and all volatiles were removed under reduced pressure. The residue was dissolved in toluene (25 mL) and the precipitated salts were removed by filtration. Subsequently, aqueous hydrogen peroxide (30 %, 1.9 mL, 2.3 eq.) was added under exclusion of light over a period of 15 minutes at 0 C and the mixture stirred for 1 h. The resulting yellowish solution was concentrated and dissolved in 50 mL dichloromethane and dried over Mg2SO4. After filtration the solvent was removed and the residue dried for 12 h under vacuum to yield 3.679 g (6.43 mmol, 80.3 %) of a slightly yellow oil. 31P{1H} NMR (121.5 MHz, CDCl3) 5[ppm] = 38.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 6.0h;Inert atmosphere; Sealed tube; Irradiation; | General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products. |