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Quality Control of [ 54288-70-9 ] Purity: 97% SDS Specification

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Product Details of [ 54288-70-9 ]

CAS No. :	54288-70-9
Formula :	C₅H₁₁Br₂N
M.W :	244.96
SMILES Code :	BrC1CCNCC1.[H]Br
MDL No. :	MFCD00191858
InChI Key :	LVTIZXGNLIKUQZ-UHFFFAOYSA-N
Pubchem ID :	2734676

Safety of [ 54288-70-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 54288-70-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	48.66
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.03 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	2.08
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.71
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.	1.83
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	1.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.5

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.67
Solubility	0.525 mg/ml ; 0.00214 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.	-1.96
Solubility	2.67 mg/ml ; 0.0109 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	-1.93
Solubility	2.86 mg/ml ; 0.0117 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	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	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.	-6.32 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	1.0 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)	1.83

Application In Synthesis of [ 54288-70-9 ]

* 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 [ 54288-70-9 ]

[ 54288-70-9 ] Synthesis Path-Downstream 1~33

1
[ 24424-99-5 ]
[ 54288-70-9 ]
[ 180695-79-8 ]

Yield	Reaction Conditions	Operation in experiment
100%		Step 1: Synthesis of 4-Bromo-piperidine-1-carboxylic acid tert-butyl ester To a suspension of 5 g (0.02 mol) of <strong>[54288-70-9]4-bromopiperidine hydrobromide</strong> salt in DCM (35 mL) are added 7.09 mL (0.04 mol) of N,N-diisopropylethyl amine dropwise at 0° C. The reaction mixture is stirred for 30 min, then a solution of 6.67 g (0.31 mol) of di-tert-butyl dicarbonate in DCM (35 mL) is added dropwise to the reaction mixture. The reaction mixture is stirred for 18 h at room temperature, then washed with 1M aqueous HCl solution (2*30 mL) and brine (30 mL). The organic layer is dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 6.9 g of 4-bromo-piperidine-l-carboxylic acid tert-butyl ester as a yellow oil. Yield quantitative; 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.46 (9H, s), 1.79-2.00 (2H, m), 2.00-2.16 (2H, m), 3.31 (2H, ddd, J=13.67, 7.73, 3.73 Hz), 3.68 (2H, ddd, J=13.55, 6.85, 3.65 Hz), 4.34 (1H, tt, J=7.69, 3.81 Hz)
100%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	To a suspension of 5 g (0.02 mol) of Compound 29 salt in DCM (35 mL) are added 7.09 mL (0.04 mol) of N,N-diisopropylethyl amine dropwise at 0° C. The reaction mixture is stirred for 30 min, then a solution of 6.67 g (0.31 mol) of di-tert-butyl dicarbonate in DCM (35 mL) is added dropwise to the reaction mixture. The reaction mixture is stirred for 18 h at room temperature, washed with 1M aqueous HCl solution (2.x.30 mL) and brine (30 mL). The organic layer is dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 6.9 g of Compound 30 as a yellow oil. Yield quantitative; 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.46 (9H, s), 1.79-2.00 (2H, m), 2.00-2.16 (2H, m), 3.31 (2H, ddd, J=13.67, 7.73, 3.73 Hz), 3.68 (2H, ddd, J=13.55, 6.85, 3.65 Hz), 4.34 (1H, tt, J=7.69, 3.81 Hz).
98%	With triethylamine; In tetrahydrofuran; at 20℃; for 48h;	Triethylamine (2.3 mL, 16.3 mmol) and di-tert-butyl dicarbonate (1.9 g, 8.6 mmol) were added to astirred suspension of <strong>[54288-70-9]4-bromopiperidine hydrobromide</strong> (2.0 g, 8.2 mmol) in THF (40 mL). Thereaction mixture was stirred for 48 h at rt. The suspension was filtered and the filter was washedwith THF. The combined filtrate was evaporated in vacuo. Purification by flash chromatography(petroleum ether 40?60 °C/EtOAc, 95:5 v/v) afforded 19 (2.11 g, 98percent) as colourless oil

References: [1]Patent: US2010/76029,2010,A1 .Location in patent: Page/Page column 42.
[2]Patent: US2011/71196,2011,A1 .Location in patent: Page/Page column 22; 23.
[3]European Journal of Medicinal Chemistry,2018,vol. 158,p. 311 - 321.
[4]Journal of the American Chemical Society,2016,vol. 138,p. 7520 - 7523.
[5]Organic Letters,2000,vol. 2,p. 6 - 10.

2
4-oxy-piperidine [ No CAS ]
[ 54288-70-9 ]

References: [1]Chemische Berichte,1915,vol. 48,p. 961.

3
[ 54288-70-9 ]
[ 98-59-9 ]
[ 347885-68-1 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5360 - 5361.
[2]Organometallics,2014,vol. 33,p. 5940 - 5943.
[3]Organic Letters,2015,vol. 17,p. 3414 - 3417.
[4]Organic and Biomolecular Chemistry,2019,vol. 17,p. 1749 - 1753.
[5]Journal of the American Chemical Society,2003,vol. 125,p. 14726 - 14727.

4
[ 54288-70-9 ]
4-(4-tert-butylphenyl)-N-tosylpiperidine [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5360 - 5361.

5
[ 54288-70-9 ]
4-(3-methyl-butyl)-1-(toluene-4-sulfonyl)-piperidine [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 14726 - 14727.

6
[ 54288-70-9 ]
[ 256430-51-0 ]

References: [1]Organic Letters,2000,vol. 2,p. 6 - 10.

7
[ 54288-70-9 ]
piperidine-4-seleninic acid dihydrotosylate [ No CAS ]

References: [1]Organic Letters,2000,vol. 2,p. 6 - 10.

8
[ 13139-17-8 ]
[ 54288-70-9 ]
[ 166953-64-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 4-methyl-morpholine; dmap; at 20℃; for 16h;	To a solution of <strong>[54288-70-9]4-bromopiperidine hydrobromide</strong> (3.0 g, 12.2 mmol) in tetrahydrofuran (30 ml) were added 1-[(benzyloxy)carbonyl]oxy}-2,5-pyrrolidinedione (3.20 g, 12.9 mmol), N-methylmorpholine (1.62 ml, 14.7 mmol) and 4-N,N-dimethylaminopyridine (30 mg) at room temperature, and stirred at room temperature for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a 1N-aqueous hydrochloric acid solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate = 1/1) to obtain benzyl 4-bromo-1-piperidinecarboxylate (3.58 g, 98percent).

References: [1]Patent: EP1403255,2004,A1 .Location in patent: Page 89.

9
[ 24424-99-5 ]
[ 312504-53-3 ]
[ 54288-70-9 ]
[ 1141486-74-9 ]
[ 1141486-72-7 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 4774 - 4782.

10
[ 312504-53-3 ]
[ 54288-70-9 ]
[ 1141486-73-8 ]
[ 1141486-75-0 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 4774 - 4782.

11
[ 54288-70-9 ]
[ 141699-66-3 ]