Structure of 32707-89-4
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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. : | 32707-89-4 |
Formula : | C9H6F6O |
M.W : | 244.13 |
SMILES Code : | OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 |
MDL No. : | MFCD00009907 |
Boiling Point : | No data available |
InChI Key : | BJTWPJOGDWRYDD-UHFFFAOYSA-N |
Pubchem ID : | 122933 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 7.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 42.57 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.14 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.8 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.37 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.6 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.79 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.54 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.2 |
Solubility | 0.155 mg/ml ; 0.000635 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.88 |
Solubility | 0.321 mg/ml ; 0.00131 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.01 |
Solubility | 0.0241 mg/ml ; 0.0000986 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) |
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 |
-5.8 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) |
1.59 |
* 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 |
---|---|---|
90% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In water; acetonitrile; at 20℃; for 6h;Green chemistry; | General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With lithium aluminium tetrahydride; In diethyl ether; at 0 - 35℃; for 10h; | Into 460 ml (0.46 mol) of a 1.0 M diethyl ether solution of aluminum lithium hydride cooled to 0C, 80 g (0.31 mol) of 3,5-bis(trifluoromethyl)benzoic acid obtained in the same manner as in Example 2 was gradually added. The reaction solution was heated to the reflux temperature (35C) while stirring under a nitrogen flow to continue the reaction for 10 h. After completion of the reaction, the reaction solution was cooled to 0C and 20 ml of water was added over 15 min. Then, 20 ml of a 15% sodium hydroxide aqueous solution and 60 ml of water were gradually added. After stirring for 30 min, the organic phase was separated by filtration and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the organic phase was analyzed by gas chromatography. It was confirmed that 58.6 g (0.24 mol) of the aimed 3,5-bis(trifluoromethyl)benzyl alcohol was produced (yield: 78%; selectivity: 91%). By vacuum distillation after removing ether, 55.9 g (0.23 mol) of 3,5-bis(trifluoromethyl)benzyl alcohol was isolated (yield: 74%). The purity determined by gas chromatography was 99% or higher. The results of ICP total elements analysis showed that none of Li, Na, K, Mg, Ca, Sr, Ba, Sc, Y, Ti, Zr, V, Nb, Cr, Mo, W, Mn, Fe, Ru, Co, Rh, Ni, Pd, Pt, Cu, Ag, Au, Zn, Cd, Al, In, Si, Sn, Pb, P, Sb and S were detected, and the content of each of group 1 and group 2 elements was 1 ppm or lower. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Purification / work up; | EXAMPLES 17 to 31 In the same manner as in Examples 2 to 16, each (fluoroalkyl)benzene derivative was produced. To reduce the impurities, the crystallization was conducted twice in Example 17 and the final distillation was repeated in the other examples. The purity, residual halogen content and residual metal content of the (fluoroalkyl)benzene derivatives are collectively shown in Table 2 |
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