Structure of 24629-25-2
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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: H -Isoleucinol
4.5
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 24629-25-2 |
Formula : | C6H15NO |
M.W : | 117.19 |
SMILES Code : | N[C@@H]([C@@H](C)CC)CO |
Synonyms : |
H -Isoleucinol
|
MDL No. : | MFCD00004731 |
InChI Key : | VTQHAQXFSHDMHT-NTSWFWBYSA-N |
Pubchem ID : | 2724027 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 34.83 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.91 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.35 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.2 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.69 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.6 |
Solubility | 29.8 mg/ml ; 0.254 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.9 |
Solubility | 14.9 mg/ml ; 0.127 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.57 |
Solubility | 31.3 mg/ml ; 0.267 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 |
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) |
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 |
-6.76 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) |
1.47 |
* 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 |
---|---|---|
4.5 g | With lithium aluminium tetrahydride; In tetrahydrofuran; for 20h;Reflux; Inert atmosphere; | L-Isoleucinol 3: L-Isoleucinol was prepared following a reported procedure61 with slight modifications. Under nitrogen, 2.5 equiv of Lithium aluminium hydride (7.2 g, 0.19 mol) was stirred in dry THF (120 mL). Then L-isoleucine (10?g, 0.08?mol) was added in portions and the suspension was refluxed for 20?h. After cooling to room temperature, ethyl acetate was added and the reaction mixture was poured carefully to concentrated sodium hydroxide solution. The organic layer was extracted with water and dried with sodium sulphate. 4.5?g of yellow liquid isoleucinol was obtained after removing the solvents. The product was used without further purification. 1H NMR (400?MHz, CDCl3): delta 0.75-0.90 (6H, m), 1.01-1.17 (1H, m), 1.22-1.36 (1H, m), 1.37-1.50 (1H, m), 2.48 (2H, br s), 2.50-2.65 (1H, m), 3.19-3.29 (1H, m), 3.57 (1H, dd, J?=?3.27, 10.64?Hz) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In tetrahydrofuran;Reflux; Inert atmosphere; Schlenk technique; | General procedure: 2-(phosphino)benzaldehyde, (1) (2,0mmol) and (S)-(+)-isoleucinol (2,2mmol) was dissolved in 20mL THF and refluxed overnight. The reaction was monitored by 1H NMR and at the end of the reaction the volatiles were removed under reduced pressure. Degassed water (10mL) and dichloromethane (50mL) were added to the remained oily product. The organic layer separated, dried under Na2SO4 and evaporated to dryness. The imines (2) were obtained as pale-yellow oil. After the spectroscopic characterization, iminophosphines (2) (0.600g, 1.5mmol) were dissolved in methanol (30mL) and NaBH4 (0.150g, 4.0mmol) was added in three portion at room temperature. The reactions were monitored by 1H NMR and at the end of the reaction the volatiles were removed under reduced pressure. Degassed water (20mL) and dichloromethane (70mL) were added. The dichloromethane phases were washed with water (20ml), brine (20mL) and dried over Na2SO4. Spectroscopically pure oily products were obtained after the removing of the volatiles under reduced pressure. |