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CAS No. : | 19748-66-4 |
Formula : | C7H15NO |
M.W : | 129.20 |
SMILES Code : | OCCCN1CCCC1 |
MDL No. : | MFCD01687769 |
InChI Key : | ZMJQROKRSPSLFH-UHFFFAOYSA-N |
Pubchem ID : | 209342 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.62 |
TPSA ? Topological Polar Surface Area: Calculated from |
23.47 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.98 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.42 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.08 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.57 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.83 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.71 |
Solubility | 25.3 mg/ml ; 0.196 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.48 |
Solubility | 42.8 mg/ml ; 0.331 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.93 |
Solubility | 15.3 mg/ml ; 0.119 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 |
-6.79 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) |
1.07 |
* 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 |
---|---|---|
69% | With potassium carbonate; In acetonitrile; | The starting material was prepared as follows: Pyrrolidine (50 g, 700 mmol), 3-chloropropanol (58.5 ml, 700 mmol) and potassium carbonate (145 g, 1.05 mol) were refluxed in acetonitrile (1 l) for 20 hours. Upon cooling to ambient temperature the precipitate was filtered off and rinsed with acetonitrile. The solvent was evaporated off and the residual oil purified by distillation under vacuum to give 3-(pyrrolidin-1-yl)propan-1-ol (62.1 g, 69%). 1H NMR Spectrum: (CDCl3) 1.75 (m, 6H); 2.55 (m, 4H); 2.75 (t, 2H); 3.85 (t, 2H); 5.50 (br s, (1H) |
69% | With potassium carbonate; In acetonitrile; | Pyrrolidine (50 g, 700 mmol), 3-chloropropanol (58.5 ml, 700 mmol) and potassium carbonate (145 g, 1.05 mol) were refluxed in acetonitrile (1 l) for 20 hours. Upon cooling to ambient temperature the precipitate was filtered off and rinsed with acetonitrile. The solvent was evaporated off and the residual oil purified by distillation under vacuum to give 3-(pyrrolidin-1-yl)propan-1-ol (62.1 g, 69%). 1H NMR Spectrum: (CDCl3) 1.75 (m, 6H); 2.55 (m, 4H); 2.75 (t, 21); 3.85 (t, 2H); 5.50 (br s, |
In acetonitrile; for 20h;Heating / reflux; | A solution of pyrrolidine (50 g, 0.7 mol) and 3-chloropropan-1-ol (66.15 g, 0.7 mol) in acetonitrile (11) containing potassium carbonate (145 g, 1.05 mol) was refluxed for 20 hours. After cooling, the mixture was filtered, the solid was washed with acetonitrile and the filtrate was evaporated. The residue was distilled at about 130C under about 70 mmHg to give 1-(3-hydroxypropyl)pyrrolidine (62.1 g, 69%). MS-ESI: 130 [MH]+ 1H NMR Spectrum: (CDCl3) 1.6-1.8 (m, 6H); 2.55 (br s, 4H); 2.75 (t, 2H); 3.85 (t, 2H); 5.2-5.8 (br s, 1H) |
With potassium carbonate; In acetonitrile; for 20h;Heating / reflux; | The N-(3-hydroxypropyl)pyrrolidine used as a starting material was prepared as follows: A mixture of 3-chloropropanol (66 g), pyrrolidine (50 g), potassium carbonate (145 g) and acetonitrile (1 L) was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was purified by distillation to give the required starting material as an oil (62 g); NMR Spectrum: (CDCl3) 1.6-1.8 (m, 6H), 2.55 (br s, 4H), 2.75 (t, 2H), 3.85 (t, 2H), 5.5 (br s, 1H). | |
With sodium hydroxide; In water; at 25 - 70℃; | tert-Butyl 4-(pyridin-3-yl)-4-(3-(pyrrolidin-1-yl)propoxy)piperidine-1-carboxylate AM-05 Stage 1. First pyrrolidine (6.95 ml) and then 3-chloropropanol (10 g, 106.3 mmol) were slowly added to a solution, heated to 50 C., of NaOH (5.06 g, 126.5 mmol) in water (4.55 ml) such that the solution did not heat up to above 70 C. After the complete addition, the mixture was first stirred at this temperature for a further 90 min and then cooled to 25 C. and stirred for a further 16 h. When the reaction had ended, the mixture was saturated with NaOH and extracted with benzene and the solvent was then stripped off on a rotary evaporator. The crude product was purified by distillation (98 C., 18 mm). | |
With potassium carbonate; In acetonitrile; for 20h;Heating / reflux; | The N-(3-hydroxypropyl)pyrrolidine used as a starting material was prepared as follows: [00726] A mixture of 3-chloropropanol (66 g), pyrrolidine (50 g), potassium carbonate (145 g) and acetonitrile (1 L) was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was purified by distillation to give the required starting material as an oil (62 g); NMR Spectrum: (CDCl3) 1.6-1.8 (m, 6H), 2.55 (br s, 4H), 2.75 (t, 2H), 3.85 (t, 2H), 5.5 (br s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In benzene; at 0℃; for 4h;Heating; Reflux; | Stage 2. Thionyl chloride (1.5 eq.) was added to a solution of 3-(pyrrolidin-1-yl)propan-1-ol (2 g, 1 eq.) in benzene (5 ml/mmol) at 0 C. The reaction mixture was then heated under reflux for 4 h. The solvent was removed completely and the solid formed was employed further without further purification. |
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