Structure of 2043-57-4
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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. : | 2043-57-4 |
Formula : | C8H4F13I |
M.W : | 474.00 |
SMILES Code : | ICCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F |
MDL No. : | MFCD00039410 |
InChI Key : | NVVZEKTVIXIUKW-UHFFFAOYSA-N |
Pubchem ID : | 74888 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H315-H318-H410 |
Precautionary Statements: | P280-P301+P312+P330-P305+P351+P338+P310 |
Class: | 9 |
UN#: | 3082 |
Packing Group: | Ⅲ |
Num. heavy atoms | 22 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 13.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 54.42 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.3 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
6.16 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
11.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.65 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
6.53 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
6.53 |
Log S (ESOL):? ESOL: Topological method implemented from |
-6.2 |
Solubility | 0.000301 mg/ml ; 0.000000634 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.94 |
Solubility | 0.00054 mg/ml ; 0.00000114 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.41 |
Solubility | 0.00184 mg/ml ; 0.00000387 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-4.82 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
1.0 |
Muegge? Muegge (Bayer) filter: implemented from |
3.0 |
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 |
3.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.46 |
* 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 water;silver nitrate; copper(II) sulfate; at 180℃;Gas phase;Conversion of starting material; | The catalyst of Preparation Example 8 (20 g) was placed in a stainless-steel reaction tube having an inner diameter of 10 mm and length of 250 mm, and was heated to 180° C. with a heater. CF3CF2 (CF2CF2)pCH2CH2I (mixture having a molar ratio of constituents of p=1/p=2/p=3/p=4/p=5/p=6=1.0/9.3/2.7/1.1/0.48/0.17) and water were introduced into a vaporizer at a rate of 2.8 g/hr and 12 g/hr, respectively, and were vaporized. Air was introduced into the reaction tube as a carrier gas at a rate of 35 cc/min. The vaporized gases were carried to the catalyst in the above reaction tube by the air to cause a catalytic reaction on the catalyst. Reaction products were recovered with an ice trap and a dry ice/methanol trap provided at the outlet of the reaction tube. The GC analysis of the products revealed that the corresponding alcohols were formed at the degree of conversion of 91percent and selectivity of 91percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Purification / work up; | Mixture of 1-iodo-1H,1H,2H,2H-perfluoroalkanes, 250 g (Mixture 2, average MW=591), and isopropanol (5 wt. %) were charged in a 400-mL Inconell shaker tube and heated to 190 C. for 12 hours. Analyses were conducted according to Test Methods 1 and 2. The level of perfluorooctyl iodide had decreased from 320 to 14 mg/kg and the level of perfluorooctanoic acid decreased from 45 to 2 mg/kg. Example 7 Mixture of 1-iodo-1H,1H,2H,2H-perfluoroalkanes, 450 g (Mixture 2, average MW=591), and monomethoxy-polyethyleneglycol (MW=350, 0.75 wt. %) were charged in a 400-mL stainless steel shaker tube and heated to 195 C. for 4 hours. Analyses were conducted according to Test Methods 1 and 2. The level of perfluorooctyl iodide had decreased from 320 to 23 mg/kg and the level of perfluorooctanoic acid decreased from 45 to 12 mg/kg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | General procedure: Perfluoroalkylethyl iodide (1.0 mol equiv.) (3-5 mmol) and NaN3 (1.0-1.5 mol equiv.) were added to dry DMSO (4 mL), a magnetic stirring bead added, and the mixture stirred under argon in a bath at 65 C for 24 h then cooled to r.t. The methoxytriethylenoxy propargyl ether 21 (1.0 mol equiv.) added, followed by sodium ascorbate (0.1 mol equiv.) and CuSO4·5H2O (0.05 mol equiv.), and additional DMSO (2 mL). The mixture was again stirred under argon at elevated temperature for 48 h. The contents were cooled and diluted with water (50 mL). The product was then extracted into Et2O (3 × 20 mL), and the combined extracts washed in turn with brine (2 × 10 mL), H2O (2 × 10 mL) and again brine (10 mL), then dried and evaporated. The residue was chromatographed on silica gel and the product eluted with a gradient of Et2O/light petroleum and distilled or characterized directly as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With silver carbonate; In toluene; at 120℃; for 72h;Inert atmosphere; | A mixture of <strong>[68631-52-7]4-hydroxypyridine-2,6-dicarboxylic acid diethyl ester</strong> (2; 5.03 g, 21.0 mmol) and Ag2CO3 (6.56 g, 23.8 mmol) in anhydrous toluene (350 mL) was stirred at 120 C under N2 for 2 h. Then, 1-iodo-2-(perfluorohexyl)ethane (7.68 mL, 31.4 mmol) was added dropwise and the reaction mixture was stirred for 3 d at 120 C. Insoluble material was removed by filtration and washed with EtOAc (200 mL). The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, CH2Cl2-EtOAc15:1; Rf = 0.33) to give 3 as a colorless solid; yield: 11.4 g (93%); mp 70 C. IR (ATR): 2916, 2849 (aliph C-H), 1716 (C=O), 1600, 1584 (arom C=C),1232, 1188 (C-O), 1143, 1118 (C-F), 1039 cm-1 (C-O). 1H NMR (500 MHz, CDCl3): delta = 7.79 (s, 2 H, PyH), 4.48 (q, 3J = 7.1 Hz, 4H, OCH2CH3), 4.45 (t, 3J = 6.5 Hz, 2 H, OCH2CH2), 2.71 (tFt, 3JH,F = 18.0Hz, 3J = 6.5 Hz, 2 H, OCH2CH2CF2), 1.45 (t, 3J = 7.1 Hz, 6 H, OCH2CH3). 13C NMR (125 MHz, CDCl3): delta = 165.9 (s, 4-PyC), 164.5 (s, PyCO2Et),150.5 (s, 2,6-PyC), 117.3 (tF, 2JC,F = 32.4 Hz, CH2CF2CF2)*, 114.1 (d, 3,5-PyC), 62.5 (t, OCH2CH3), 60.9 (t, OCH2CH2CF2), 31.0 [t(tF), 2JC,F = 21.8Hz, CH2CH2CF2], 14.2 (q, OCH2CH3). * Only visible in the HMBC spectrum. 19F NMR (470 MHz, CDCl3): delta = -80.8 (s, 3 F, CF3), -113.2 (s, 2 F,CH2CF2), -121.8 (s, 2 F, CH2CF2CF2), -122.8 (s, 2 F, CF2CF3), -123.5 (s, 2F, CF2CF2CF3), -126.1 (s, 2 F, CH2CF2CF2CF2). MS (EI): m/z = 586 [M + H]+, 585 [M]+?, 584 [M - H]+, 512 [M -CO2CH2CH3]+, 439 [M - C6H10O4]+.HRMS (EI): m/z [M]+? calcd for C19H16F13NO5: 585.0821; found:585.0820. |
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