Structure of 5337-63-3
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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. : | 5337-63-3 |
Formula : | C14H18O3 |
M.W : | 234.29 |
SMILES Code : | O=C(OCC)C(C(C)=O)CCC1=CC=CC=C1 |
MDL No. : | MFCD22374908 |
InChI Key : | GPRDAMCHHGGJNX-UHFFFAOYSA-N |
Pubchem ID : | 219459 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.43 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 66.54 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.57 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.68 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.43 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.67 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.78 |
Solubility | 0.389 mg/ml ; 0.00166 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.24 |
Solubility | 0.134 mg/ml ; 0.000571 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.08 |
Solubility | 0.0195 mg/ml ; 0.0000832 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) |
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 |
-5.83 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 |
0.0 |
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) |
2.32 |
* 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 |
---|---|---|
81% | Aceto-alpha-phenyl-gamma-butyric acid ethyl ester (5 g, 27 mmol) was added dropwise to H2SO4 (30 mL) at -20C. The mixture is stirred at this temperature for 4 h and was then cautiously hydrolyzed in of a cold water (300 mL). The white precipitate was filtered of and dried overnight. The crude acid was recrystallized with a benzene-hexane mixture to yield white crystals (81%. mp. 127C). 1H NMR (200 MHz, CDCl3): delta 2.57 (s, 3 H), 2.63-2.68 (m, 2 H), 2.77-2.81 (m, 2 H), 7.17-7.53 (m, 4 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium carbonate; In water; toluene; | Reference Example 3 In the same manner as described in Reference Example 1, except that 55.5 g (300 mmol) of (2-bromoethyl)benzene, 42.9 g (330 mmol) of ethyl 3-oxobutanoate, 27.8 g of toluene, 103 g (748 mmol) of potassium carbonate, and 2.08 g of water were used, 77.4 g of the crude product of ethyl 3-oxo-2-(2-phenylethyl)butanoate was obtained. The ethyl 3-oxo-2-(2-phenylethyl)butanoate content in the crude content was 68.9% by weight (77% yield). |
With potassium carbonate; In water; toluene; | Example 11 To a mixture of 8.46 g (46 mmol) of (2-bromoethyl)benzene, 6.55 g (50 mmol) of ethyl 3-oxo-butanoate, and 4.23 g of toluene were added 15.8 g (115 mmol) of potassium carbonate and 0.21 g of water, and the mixture was heated to 75C and then stirred at the same temperature for 14.3 hours. The reaction mixture was cooled to 70C, and after the addition of 21.4 g of water and 1.7 g of toluene, was subjected to phase separation. The organic layer was washed twice with 10.7 g of water and then concentrated under reduced pressure to give 10.4 g of the crude product of ethyl 3-oxo-2-(2-phenylethyl)butanoate. | |
With potassium carbonate; In water; toluene; | Reference Example 1 To a mixture of 55.5 g (300 mmol) of (2-bromoethyl)benzene and 42.9 g (330 mmol) of ethyl 3-oxobutanoate were added 124 g (894 mmol) of potassium carbonate and 2.49 g of water, and the mixture was heated to 70C and then stirred at the same temperature for 15 hours. The reaction mixture, alter the addition of 198 g of water and 27.8 g of toluene, was subjected to phase separation. The organic layer was washed twice with 70.1 g of water and then concentrated under reduced pressure to give 70.4 g of the crude product of ethyl 3-oxo-2-(2-phenylethyl)butanoate. The ethyl 3-oxo-2-(2-phenylethyl)butanoate content in the crude product was 84.4% by weight (86% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Then, 1050 g (2.79 mol) of the crude product of ethyl 3-oxo-2-(2-phenylethyl)butanoate thus obtained was cooled to 5C, to which 908 g (3.14 mol) of 44% nitrosylsulfuric acid/sulfuric acid solution was added dropwise at 2-5C over 3.6 hours, and the mixture was stirred at the same temperature for 3.8 hours. |
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