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Structure of (S)-BINOL
CAS No.: 18531-99-2
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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.
Synonyms: (S)-1,1'-Bi-2,2'-naphthol; S-(-)-2,2'-Dihydroxy-1,1'-binaphthyl; (S)-(-)-1,1'-Bi-2-naphthol
4.5
*For Research Use Only !
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| CAS No. : | 18531-99-2 |
| Formula : | C20H14O2 |
| M.W : | 286.32 |
| SMILES Code : | OC1=CC=C2C=CC=CC2=[C@]1[C@]3=C4C=CC=CC4=CC=C3O |
| Synonyms : |
(S)-1,1'-Bi-2,2'-naphthol; S-(-)-2,2'-Dihydroxy-1,1'-binaphthyl; (S)-(-)-1,1'-Bi-2-naphthol
|
| MDL No. : | MFCD00004068 |
| InChI Key : | PPTXVXKCQZKFBN-UHFFFAOYSA-N |
| Pubchem ID : | 11762 |
| GHS Pictogram: |
|
| Signal Word: | Danger |
| Hazard Statements: | H301-H315-H319 |
| Precautionary Statements: | P301+P310+P330-P302+P352-P305+P351+P338 |
| Class: | 6.1 |
| UN#: | 2811 |
| Packing Group: | Ⅲ |
| Num. heavy atoms | 22 |
| Num. arom. heavy atoms | 20 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 1 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 2.0 |
| Molar Refractivity | 90.94 |
| TPSA ? Topological Polar Surface Area: Calculated from |
40.46 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 |
5.34 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.07 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.02 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.6 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.4 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-5.59 |
| Solubility | 0.000743 mg/ml ; 0.00000259 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-5.94 |
| Solubility | 0.000327 mg/ml ; 0.00000114 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.11 |
| Solubility | 0.0000222 mg/ml ; 0.0000000776 mol/l |
| Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
| 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 |
-4.26 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) |
1.97 |
* 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.

[ 40138-16-7 ]
[ 18531-99-2 ]
[ 180683-64-1 ]
[ 18531-99-2 ]
[ 83883-26-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |

A840497 [602-09-5]
[1,1'-Binaphthalene]-2,2'-diol
Reason: Racemic-enantiomer

A290939 [18531-94-7]
(R)-[1,1'-Binaphthalene]-2,2'-diol
Reason: Optical isomers