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Chemical Structure| 19748-66-4 Chemical Structure| 19748-66-4
Chemical Structure| 19748-66-4

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CAS No.: 19748-66-4

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Product Details of [ 19748-66-4 ]

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

Safety of [ 19748-66-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 19748-66-4 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

23.47 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.98
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.42
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.08
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.57
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.83

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.71
Solubility 25.3 mg/ml ; 0.196 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.48
Solubility 42.8 mg/ml ; 0.331 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.93
Solubility 15.3 mg/ml ; 0.119 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.79 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.07

Application In Synthesis [ 19748-66-4 ]

* 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.

  • Downstream synthetic route of [ 19748-66-4 ]

[ 19748-66-4 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 123-75-1 ]
  • [ 627-30-5 ]
  • [ 19748-66-4 ]
YieldReaction ConditionsOperation 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).

  • 2
  • [ 19748-66-4 ]
  • [ 1871-76-7 ]
  • [ 127158-39-8 ]
  • 3
  • [ 19748-66-4 ]
  • [ 7037-44-7 ]
  • cyclopentyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 4
  • [ 19748-66-4 ]
  • [ 49802-71-3 ]
  • cyclohexyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 5
  • [ 19748-66-4 ]
  • [ 874512-36-4 ]
  • cyclopent-2-enyl-[2]thienyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 6
  • [ 19748-66-4 ]
  • [ 853919-58-1 ]
  • cyclohex-2-enyl-[2]thienyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 7
  • [ 19748-66-4 ]
  • [ 24168-51-2 ]
  • fluorene-9-carboxylic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 8
  • [ 19748-66-4 ]
  • [ 91767-44-1 ]
  • 4-isopropoxy-2,6-dimethyl-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 9
  • [ 19748-66-4 ]
  • [ 91767-43-0 ]
  • 2,6-dimethyl-4-propoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 10
  • [ 19748-66-4 ]
  • [ 36823-82-2 ]
  • 4-isopropoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 11
  • [ 19748-66-4 ]
  • [ 40782-58-9 ]
  • 4-propoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 12
  • [ 19748-66-4 ]
  • [ 73331-32-5 ]
  • 2-cyclopentyl-valeric acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 13
  • [ 19748-66-4 ]
  • [ 857827-17-9 ]
  • 2-cyclopent-2-enyl-valeric acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 14
  • [ 19748-66-4 ]
  • 2-cyclopent-2-enyl-hexanoyl chloride [ No CAS ]
  • 2-cyclopent-2-enyl-hexanoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 15
  • [ 19748-66-4 ]
  • [ 73331-33-6 ]
  • cyclopent-2-enyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 16
  • [ 19748-66-4 ]
  • [ 872290-82-9 ]
  • cyclohex-2-enyl-cyclopent-2-enyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 17
  • [ 19748-66-4 ]
  • cyclohex-2-enyl-phenyl-acetyl chloride [ No CAS ]
  • cyclohex-2-enyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 18
  • [ 19748-66-4 ]
  • [ 4521-61-3 ]
  • [ 101867-45-2 ]
  • 19
  • [ 19748-66-4 ]
  • [ 10263-19-1 ]
  • [ 102021-80-7 ]
  • 20
  • [ 19748-66-4 ]
  • [ 18780-68-2 ]
  • [ 118952-80-0 ]
  • 21
  • [ 19748-66-4 ]
  • [ 33863-86-4 ]
  • 4-butoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]
  • 22
  • [ 19748-66-4 ]
  • [ 39743-20-9 ]
YieldReaction ConditionsOperation 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.
  • 23
  • [ 19748-66-4 ]
  • [ 32633-91-3 ]
  • [ 47357-40-4 ]
  • 24
  • [ 19748-66-4 ]
  • [ 94231-78-4 ]
  • [ 99004-32-7 ]
  • 26
  • [ 123-75-1 ]
  • [ 504-63-2 ]
  • [ 19748-66-4 ]
  • [ 1012-29-9 ]
 

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