Structure of 13105-53-8
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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. : | 13105-53-8 |
Formula : | C12H17NO2 |
M.W : | 207.27 |
SMILES Code : | O=C(OCC1=CC=CC=C1)NCCCC |
MDL No. : | MFCD00158472 |
InChI Key : | VQJDBGSINGXXEB-UHFFFAOYSA-N |
Pubchem ID : | 4410025 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H412 |
Precautionary Statements: | P273 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.42 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 59.92 |
TPSA ? Topological Polar Surface Area: Calculated from |
38.33 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.89 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.69 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.56 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.38 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.36 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.58 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.65 |
Solubility | 0.46 mg/ml ; 0.00222 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.15 |
Solubility | 0.148 mg/ml ; 0.000712 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.15 |
Solubility | 0.0146 mg/ml ; 0.0000706 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) |
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) |
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 |
-5.65 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 |
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) |
2.02 |
* 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 |
---|---|---|
92% | at 50℃; for 0.0333333 h; Microwave irradiation; Green chemistry | General procedure: Benzylcholoroformate Cbz-Cl (1 mmol) was added to amine (1 mmol) and the mixture was subjected to the microwave irradiation (100W) for the appropriate time (tables 2, 3, 4 and 5). After completion of the reaction (monitored by TLC) dichloromethane: methanol (98/2), the reaction mixture was treating with n-hexane (15–20 mL) and was allowed to stand at room temperature overnight. The solid products were collected by filtration, washed with n-hexane and dried to give the N-Cbz derivatives in good to excellent yields. During the reaction, the formation of hydrogen chloride (gas) was observed, confirming the protection of all amines structures proposal. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With caesium carbonate In N,N-dimethyl-formamide at 25 - 100℃; for 4 h; Autoclave | General procedure: An amine (2.85 mmol) and anhydrous DMF (15 mL) were introduced into an autoclave. The autoclave was purged twice with CO2 and the reaction was conducted at 25 °C under 1 MPa of CO2. After 1 h, an appropriate amount of the catalyst, cesium carbonate (9 mmol), and alkyl or benzyl chloride (9 mmol) was added. The autoclave was purged twice with CO2 and the mixture was stirred at 100 °C under 1 MPa of CO2 for 3 h. After cooling to room temperature, the excess of CO2 was vented, and the catalyst was separated by filtration. The post-reaction mixture waspoured into water (30 mL) and extracted with ethyl acetate (3 x 30 mL). The organic layer was washed with brine (30 mL) and water (2 x 30 mL). The organic layer was dried over anhydrous magnesium sulfate, and evaporated to give crude alkyl carbamate in the form of a yellow oil. |
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