Structure of 2-Aminophenethyl alcohol
CAS No.: 5339-85-5
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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. : | 5339-85-5 |
Formula : | C8H11NO |
M.W : | 137.18 |
SMILES Code : | OCCC1=CC=CC=C1N |
MDL No. : | MFCD00007754 |
InChI Key : | ILDXSRFKXABMHH-UHFFFAOYSA-N |
Pubchem ID : | 79282 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 41.78 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.45 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.81 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.06 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.33 |
Solubility | 6.41 mg/ml ; 0.0468 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.06 |
Solubility | 11.9 mg/ml ; 0.0867 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.24 |
Solubility | 0.784 mg/ml ; 0.00571 mol/l |
Class? Solubility class: Log S scale |
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 |
-6.77 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 |
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) |
1.0 |
* 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 |
---|---|---|
100% | EXAMPLE 5 The same procedure of Example 1 was repeated, except for increasing the amount of sodium hydroxide to 0.06 g (0.0015 mol). When uptake of hydrogen ceased in 43 minutes, the reaction was complete. The reaction mixture was cooled and allowed to stand. The supernatant liquor was recovered by decantation and analyzed by gas chromatography. As a result, the conversion of 2-(o-nitrophenyl)ethanol was 100percent and the yield of 2-(o-aminophenyl)ethanol was 99.5percent. | |
100% | EXAMPLE 6 The same procedure of Example 5 was repeated, except for using the catalyst spent in Example 5. The reaction was complete in 74 minutes when uptake of hydrogen ceased. As a result of gas chromatography of the reaction mixture, the conversion of 2-(o-nitrophenyl)ethanol was 100percent, and the yield of 2-(o-aminophenyl)ethanol was 99.2percent. | |
100% | As a result, the conversion of 2-(o-nitrophenyl)ethanol was 100percent, and the yield of 2-(o-aminophenyl)ethanol was 98.7percent. |
47.0% | aluminum nickel; | COMPARATIVE EXAMPLE 2 The procedure of Comparative Example 1 was repeated, except for using the Raney nickel catalyst spent in Comparative Example 1. The reaction required 300 minutes for completion. As a result of gas chromatography of the reaction mixture, the conversion of 2-(o-nitrophenyl)ethanol was 47.0percent and the yield of 2-(o-aminophenyl)ethanol was 42.6percent. |
00% | EXAMPLE 2 The same procedure of Example 1 was repeated, except for increasing the amount of sodium hydroxide to 0.09 g (0.0023 mol). After 20 minutes' reaction, no uptake of hydrogen was observed, and the resulting reaction mixture was analyzed by gas chromatography. As a result, the conversion of 2-(o-nitrophenyl)ethanol was 00percent, and the yield of 2-(o-aminophenyl)ethanol was 98.9percent. | |
With potassium hydroxide; | EXAMPLE 4 The same procedure of Example 1 was repeated, except for replacing sodium hydroxide with 0.09 g (0.0016 mol) of potassium hydroxide. When uptake of hydrogen ceased in 33 minutes, the reaction was stopped. Gas chromatography of the reaction mixture revealed that the conversion of 2-(o-nitrophenyl)ethanol and the yield of 2-(o-aminophenyl)ethanol were 100percent and 98.5percent, respectively. |
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