Structure of 607-01-2
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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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CAS No. : | 607-01-2 |
Formula : | C14H15P |
M.W : | 214.24 |
SMILES Code : | CCP(C1=CC=CC=C1)C2=CC=CC=C2 |
MDL No. : | MFCD00015170 |
InChI Key : | WUOIAOOSKMHJOV-UHFFFAOYSA-N |
Pubchem ID : | 69082 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H319-H372-H410 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 |
Class: | 9 |
UN#: | 3082 |
Packing Group: | Ⅲ |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 69.74 |
TPSA ? Topological Polar Surface Area: Calculated from |
13.59 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.98 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.42 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.14 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.41 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.74 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.74 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.72 |
Solubility | 0.0411 mg/ml ; 0.000192 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.39 |
Solubility | 0.0882 mg/ml ; 0.000412 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.82 |
Solubility | 0.000322 mg/ml ; 0.0000015 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) |
Yes |
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 |
1.0 |
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) |
4.16 |
* 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 |
---|---|---|
75%Spectr. | With chloro-trimethyl-silane; magnesium; at 20℃; for 2h; | General procedure: To a mixture of Mg powder (8 mmol, 4 mol equiv), Me3SiCl (6 mmol, 3 mol equiv), and DMI (8 mL) was added 2a (2 mmol), and the whole mixture was stirred for 2 h at room temperature. To the reaction mixture was added satd aq (NH4)2CO3, and the mixture was extracted with Et2O (10 mL 3). The combined organic layers were washed with satd aq NaCl, dried over Na2SO4, and concentrated under reduced pressure. The resultant was analyzed by 31P NMR to find that 1a and 2a were obtained in 97:3 ratio. The desired 1a was obtained in 96% yield after purification by silica gel column chromatography (hexane/AcOEt = 5:1) (Table 1, entry 1). |
95%Chromat. | With [AlH3(triethylamine)]; In hexane; at 20℃; for 0.166667h;Inert atmosphere; Schlenk technique; | General procedure: Triphenylphosphine oxide or sulfide (1 mmol), dry hexane (1 mL), and Ic (1 mmol) were added to a Schlenk tube under the atmosphere of nitrogen. The reaction was carried out at room temperature for 10 min and monitored by TLC. Upon completion of the process the reaction mixture was filtered by silica gel and washed several times with ethyl acetate. Ethyl acetate was evaporated and the residue purified by flash chromatography on silica gel with pure cyclohexane toafford the desired phosphine. The yield was determined by GC without additional purification. |