3161-51-1|3-(Dibenzylamino)propan-1-ol| Ambeed

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Quality Control of [ 3161-51-1 ] Purity: 97% SDS Specification

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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 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.99
Log P_o/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 P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.77
Log P_o/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 P_o/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 P_o/w? Consensus Log P_o/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 ]

References: [1]Chimica Therapeutica,1966,vol. 1,p. 456 - 460.

2
[ 103-49-1 ]
[ 627-18-9 ]
[ 3161-51-1 ]

References: [1]Chimica Therapeutica,1966,vol. 1,p. 456 - 460.

3
[ 503-30-0 ]
[ 103-49-1 ]
[ 3161-51-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2597 - 2602.

4
[ 128017-04-9 ]
[ 3161-51-1 ]

References: [1]Synthesis,1990,p. 153 - 156.

5
[ 3161-51-1 ]
[ 98346-35-1 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 3011 - 3014.
[2]Tetrahedron Letters,2008,vol. 49,p. 1648 - 1651.

Yield	Reaction Conditions	Operation 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 ]

References: [1]Organic Letters,2005,vol. 7,p. 2361 - 2364.

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 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4059 - 4071.

9
[ 100-52-7 ]
[ 3161-51-1 ]

References: [1]Synthesis,1990,p. 153 - 156.

10
[ 4720-29-0 ]
[ 3161-51-1 ]

References: [1]Synthesis,1990,p. 153 - 156.

11
cyclohexyl-1-1,2-ethanediol [ No CAS ]
[ 3161-51-1 ]
[ 144728-78-9 ]

Yield	Reaction Conditions	Operation 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:

References: [1]Patent: US5223633,1993,A .

12
[ 3161-51-1 ]
[ 1005192-49-3 ]

References: [1]Tetrahedron Asymmetry,2007,vol. 18,p. 2695 - 2711.

13
[ 100-39-0 ]
[ 156-87-6 ]
[ 3161-51-1 ]

Yield	Reaction Conditions	Operation 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]+.

References: [1]Tetrahedron Asymmetry,2007,vol. 18,p. 2695 - 2711.
[2]European Journal of Medicinal Chemistry,2018,vol. 150,p. 655 - 666.
[3]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 106 - 113.

14
[ 476192-42-4 ]
[ 3161-51-1 ]
[ 476192-43-5 ]

Yield	Reaction Conditions	Operation 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]+.

References: [1]Patent: US2004/10019,2004,A1 .Location in patent: Page 149.

15
[ 100-52-7 ]
[ 156-87-6 ]
[ 3161-51-1 ]

References: [1]Synthesis,2010,p. 1673 - 1677.

16
[ 3161-51-1 ]
[ 156-87-6 ]

References: [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 735 - 738.

17
[ 3161-51-1 ]
[ 1363467-49-5 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 1627 - 1629.
[2]European Journal of Medicinal Chemistry,2018,vol. 150,p. 655 - 666.

18
[ 3161-51-1 ]
[ 124-63-0 ]
[ 1363467-46-2 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 1627 - 1629.
[2]European Journal of Medicinal Chemistry,2018,vol. 150,p. 655 - 666.

19
[ 3161-51-1 ]
[ 79-44-7 ]
3-(dibenzylamino)propyl dimethylcarbamate [ No CAS ]

References: [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 106 - 113.

20
[ 3161-51-1 ]
3-(dibenzylamino)-1-(p-tolyl)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 166 - 169.

21
[ 3161-51-1 ]
(R)-(+)-3-(dibenzylamino)-1-(p-tolyl)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 166 - 169.

22
[ 3161-51-1 ]
[ 146176-60-5 ]
[ 144728-78-9 ]

References: [1]Organic Letters,2017,vol. 19,p. 166 - 169.

23
[ 3161-51-1 ]
N1-(3-(dibenzylamino)propyl)cyclohexane-1,4-diamine hydrochloride [ No CAS ]