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Chemical Structure| 3161-51-1 Chemical Structure| 3161-51-1

Structure of 3161-51-1

Chemical Structure| 3161-51-1

3-(Dibenzylamino)propan-1-ol

CAS No.: 3161-51-1

4.5 *For Research Use Only !

Cat. No.: A508446 Purity: 97%

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Product Details of [ 3161-51-1 ]

CAS No. :3161-51-1
Formula : C17H21NO
M.W : 255.36
SMILES Code : OCCCN(CC1=CC=CC=C1)CC2=CC=CC=C2
MDL No. :MFCD00075550
InChI Key :LKOXRTJFYFGTKJ-UHFFFAOYSA-N
Pubchem ID :4437007

Safety of [ 3161-51-1 ]

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

Computational Chemistry of [ 3161-51-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.29
Num. rotatable bonds 7
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 79.18
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

23.47 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.99
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

2.92
Log Po/w (WLOGP)?

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

2.77
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.

3.16
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

3.48
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.06

Water Solubility

Log S (ESOL):?

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

-3.27
Solubility 0.138 mg/ml ; 0.000539 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-3.07
Solubility 0.215 mg/ml ; 0.000843 mol/l
Class?

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

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

-5.7
Solubility 0.000506 mg/ml ; 0.00000198 mol/l
Class?

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

Moderately 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

Yes
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

Yes
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

Yes
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.

-5.78 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

0.0
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<0.0
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)

1.4

Application In Synthesis of [ 3161-51-1 ]

* 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 [ 3161-51-1 ]

[ 3161-51-1 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 3161-51-1 ]
  • [ 15513-04-9 ]
  • [ 15570-37-3 ]
  • 2
  • [ 103-49-1 ]
  • [ 627-18-9 ]
  • [ 3161-51-1 ]
  • 3
  • [ 503-30-0 ]
  • [ 103-49-1 ]
  • [ 3161-51-1 ]
  • 4
  • [ 128017-04-9 ]
  • [ 3161-51-1 ]
YieldReaction ConditionsOperation in experiment
79% B! Starting from the compound under A! (70 g, 0.247 mole) and lithium aluminium hydride (12.6 g, 0.33 mole) in THF (210+490 ml), and following the procedure of Example[13,C], there were obtained 63.7 g of a crude which was distilled under vacuum to give 50 g of 3-(N,N-dibenzylamino)propanol (yield: 79%) (b.p.--150-152 C./1 mmHg).
  • 7
  • [ 3161-51-1 ]
  • 3-N-benzylaminopropyl benzoate [ No CAS ]
  • 8
  • [ 906069-29-2 ]
  • [ 3161-51-1 ]
  • 3-(N,N-dibenzylamino)-1-propyl(2R)-5,5-dimethyl-1-(3,3-dimethyl-1,2-dioxobutyl)-2-(4-thiazolidine)carboxylate [ No CAS ]
  • 9
  • [ 100-52-7 ]
  • [ 3161-51-1 ]
  • 10
  • [ 4720-29-0 ]
  • [ 3161-51-1 ]
  • 11
  • cyclohexyl-1-1,2-ethanediol [ No CAS ]
  • [ 3161-51-1 ]
  • [ 144728-78-9 ]
YieldReaction ConditionsOperation in experiment
3-(N,N-Dibenzylamino)propyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate STR41 3.53 g (58%) of the title compound were obtained analogously as colorless crystals from 2.87 g (15.0 mmol) of the carbamoyl chloride CbxCl from Example 1, 807 mg (27.0 mmol) of 80 per cent sodium hydride and 4.97 g (19.5 mmol) of <strong>[3161-51-1]3-(N,N-dibenzylamino)-1-propanol</strong> after purification of the crude product on silica gel (ether/pentane 1:1). RF =0.41 (silica gel, ether/pentane 1:2), m.p.: 65 C. (from the melt). Example 8 of the formula II:
  • 12
  • [ 3161-51-1 ]
  • [ 1005192-49-3 ]
  • 13
  • [ 100-39-0 ]
  • [ 156-87-6 ]
  • [ 3161-51-1 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate; In acetone; at 20℃; General procedure: A mixture of the corresponding benzyl chloride/bromide (2.1 eq.), 3-aminopropanol (1.0 eq.) and K2CO3 (5.0 eq.) in acetone, dichloromethane or dimethylformamide was stirred at room temperature. After completion of the reaction (12-16h) monitored by TLC, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the corresponding aminoalcohol. 4.1.1 2a: 3-(dibenzylamino)propan-1-ol Conditions: Benzylbromide in acetone. Yellow oil, (70%). Rf (Cyclohexane/EtOAc 8:2)?=?0.26. 1H NMR (300?MHz, MeOD): delta?=?7.35-7.21 (m, 10H), 3.56-3.53 (m, 6H), 2.55 (t, J?=?6.5?Hz, 2H), 1.76 (m, 2H) ppm. 13C NMR (75?MHz, D2O): delta = 138.1, 128.9, 128.2, 63.4, 58.3, 52.7, 27.9 ppm. HRMS-ESI(+): calcd for C17H21NO: 255.1623, found: 256.1629 [M+H]+.
  • 14
  • [ 476192-42-4 ]
  • [ 3161-51-1 ]
  • [ 476192-43-5 ]
YieldReaction ConditionsOperation in experiment
70% To a solution of <strong>[3161-51-1]3-(dibenzylamino)-1-propanol</strong> (4.3 g, 16.88 mmol) in anhydrous N,N-dimethylformamide (35 mL) was added sodium hydride (1.3 g, 32.35 mmol; 60% dispersion in mineral oil). The reaction mixture was stirred for 15 min, then cooled to 0 C. in an ice bath and treated with a solution of the product from Part H (6.0 g, 14.07 mmol) in anhydrous N,N-dimethylformamide (15 mL). After the addition was completed, the ice bath was removed and the reaction was allowed to stir at ambient temperature for 18 hr. The reaction was quenched with water and concentrated in vacuo. The oily residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×). The organic extracts were combined and washed with brine (3×), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude yellow solid was re-crystallized from hot acetonitrile. 6.5 g (70%) of the pure desired product was collected as a white powder. ESMS m/z=662 [M+H]+.
  • 15
  • [ 100-52-7 ]
  • [ 156-87-6 ]
  • [ 3161-51-1 ]
  • 18
  • [ 3161-51-1 ]
  • [ 124-63-0 ]
  • [ 1363467-46-2 ]
YieldReaction ConditionsOperation in experiment
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 16h; General procedure: Methanesulfonyl chloride (2.0 eq.) in DCM (0.22M) was cooled at 0C using an ice bath. A mixture of the corresponding aminoalcohol (1.0 eq.), di-isopropylethylamine (5.0 eq.) and DMAP (10mol%) in DCM (0.44M) was added dropwise under stirring. The reaction mixture was stirred at low temperature for 5min and then, at room temperature for 16h. Then, the dark red-brown reaction mixture was poured into a mixture of ice-water and DCM and the organic layer was separated. The aqueous phase was extracted with DCM three times. The combined organic layers were washed with water and brine, dried with MgSO4 and evaporated to give the mesylated intermediate as pale yellow gummy solid. The product was used without further purification. 4.2.1 3a: 3-(dibenzylamino)propyl methanesulfonate Rf (Cyclohexane/EtOAc 8:2)?=?0.28. 1H NMR (300?MHz, CDCl3): delta?=?7.35-7.32 (m, 10H), 4.24 (t, 2H, J?=?6.5?Hz), 3.55 (s, 4H), 2.82 (s, 3H), 2.55 (t, 2H, J?=?6.5?Hz), 1.92 (qt, 2H, J?=?6.5?Hz). 13C NMR (75?MHz, CDCl3): delta?=?138.6, 128.8, 127.4, 126.7, 67.6, 61.0, 52.8, 37.6, 26.7.
  • 19
  • [ 3161-51-1 ]
  • [ 79-44-7 ]
  • 3-(dibenzylamino)propyl dimethylcarbamate [ No CAS ]
  • 20
  • [ 3161-51-1 ]
  • 3-(dibenzylamino)-1-(p-tolyl)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate [ No CAS ]
  • 21
  • [ 3161-51-1 ]
  • (R)-(+)-3-(dibenzylamino)-1-(p-tolyl)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate [ No CAS ]
  • 22
  • [ 3161-51-1 ]
  • [ 146176-60-5 ]
  • [ 144728-78-9 ]
  • 23
  • [ 3161-51-1 ]
  • N<SUP>1</SUP>-(3-(dibenzylamino)propyl)cyclohexane-1,4-diamine hydrochloride [ No CAS ]
  • 24
  • [ 3161-51-1 ]
  • tert-butyl (4-(bis(3-(dibenzylamino)propyl)amino)butyl)carbamate [ No CAS ]
  • 25
  • [ 3161-51-1 ]
  • tert-butyl (4-((3-(dibenzylamino)propyl)amino)cyclohexyl)carbamate [ No CAS ]
  • 26
  • [ 3161-51-1 ]
  • N<SUP>1</SUP>-(3-(dibenzylamino)propyl)butane-1,4-diamine hydrochloride [ No CAS ]
  • 27
  • [ 3161-51-1 ]
  • N<SUP>1</SUP>,N<SUP>1</SUP>-bis(3-(dibenzylamino)propyl)butane-1,4-diamine hydrochloride [ No CAS ]
  • 28
  • [ 107-18-6 ]
  • [ 103-49-1 ]
  • [ 3161-51-1 ]
 

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