(S)-1-(4-(Trifluoromethyl)phenyl)propan-1-amine

Cat.NO.:A1258129 Purity:95%

Product Details of [ 1003887-67-9 ]

CAS No. :	1003887-67-9
Formula :	C₁₀H₁₂F₃N
M.W :	203.20
SMILES Code :	N[C@@H](CC)C1=CC=C(C(F)(F)F)C=C1
MDL No. :	MFCD08439002
InChI Key :	YOETTZCHIABKPH-VIFPVBQESA-N
Pubchem ID :	51440024

Safety of [ 1003887-67-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H318-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501
Class:	8
UN#:	2735
Packing Group:	Ⅲ

Computational Chemistry of [ 1003887-67-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	48.73
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.36
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	2.59
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.94
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.	3.19
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	2.98
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.85
Solubility	0.287 mg/ml ; 0.00141 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.	-2.79
Solubility	0.333 mg/ml ; 0.00164 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	-3.77
Solubility	0.0344 mg/ml ; 0.000169 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	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.	-5.7 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)	1.68

Application In Synthesis of [ 1003887-67-9 ]

* 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 [ 1003887-67-9 ]

[ 1003887-67-9 ] Synthesis Path-Downstream 1~5

1
[ 1003887-66-8 ]
[ 1003887-67-9 ]

Yield	Reaction Conditions	Operation in experiment
23%	With periodic acid; methylamine; In methanol; water; at 0 – 20℃;	40% MeNH2 in water (11.3 mL, 30 eq) was added to a solution of (S)-2-(S)-l-[4-(trifiuoromethyl)phenyl]propylamino-2- phenylethanol (1.43 g, 4.42 mmol) in MeOH (17 mL). The solution was cooled to O0C and a solution OfH5IOe (6.0 g, 6 eq) in water (17 mL) was added dropwise. A white precipitate formed. The resulting reaction mixture was stirred at room temperature overnight. Et2O (85 mL) and water (57 mL) were added. The organic layer was separated, and the aqueous layer was extracted with Et2O (85 mL). The combined organic layers were concentrated to 11 mL and cooled to O0C. IN HCl (17 mL) was added dropwise followed by stirring at room temperature for 1 h. The solution was cooled to O0C, basified with solid NaOH pellets to pH 12 and extracted with Et2O (2 X 85 mL). The combined organic layers were dried over Na2SO4 and concentrated. Purification with flash column chromatography eluting with 4% 7 N ammonia in MeOH/DCM provided the desired product as pale yellow oil (0.245 g, 23%). 1H NMR (300 MHz, d-CHCl3) δ 0.85 (t, 3H), 1.67 (m, 2H), 3.87 (t, IH), 7.41 (d, 2H), 7.56 (d, 2H). MS: calculated: 203.09, found (MH+): 203.9.

References: [1]Patent: WO2008/11392,2008,A2 .Location in patent: Page/Page column 35-36.

2
[ 1003887-67-9 ]
[ 32315-10-9 ]
[ 1003887-68-0 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 3.0h;	Triphosgene (43.5 mg,0.15 mmol) in dichloromethane (1 mL) was added dropwise to (S)-l-(4-(trifiuoromethyl) <n=”39″/>phenyl)propylamine (89.4 mg, 0.44 mmol) in dichloromethane (1 niL). The mixture was stirred at room temperature for 3 h; a precipitate formed. This material was used directly to the next step.

References: [1]Patent: WO2008/11392,2008,A2 .Location in patent: Page/Page column 35-37.

3
[ 711-33-1 ]
[ 1003887-67-9 ]

References: [1]Green Chemistry,2017,vol. 19,p. 474 – 480.

4
[ 67081-98-5 ]
[ 1003887-67-9 ]

References: [1]Green Chemistry,2017,vol. 19,p. 474 – 480.

5
[ 1003887-67-9 ]
[ 108-24-7 ]
(S)-N-acetyl-1-<4-(trifluoromethyl)phenyl>propylamine [ No CAS ]

References: [1]Green Chemistry,2017,vol. 19,p. 474 – 480.

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(S)-1-(4-(Trifluoromethyl)phenyl)propan-1-amine

Product Details of [ 1003887-67-9 ]

Safety of [ 1003887-67-9 ]

Computational Chemistry of [ 1003887-67-9 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 1003887-67-9 ]

[ 1003887-67-9 ] Synthesis Path-Downstream 1~5

Details

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