170564-98-4|(R)-1-Phenyl-3-propanolamine| Ambeed

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Quality Control of [ 170564-98-4 ] Purity: 95% SDS Specification

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Product Details of [ 170564-98-4 ]

CAS No. :	170564-98-4
Formula :	C₉H₁₃NO
M.W :	151.21
SMILES Code :	N[C@@H](C1=CC=CC=C1)CCO
MDL No. :	MFCD01311791
InChI Key :	SEQXIQNPMQTBGN-SECBINFHSA-N
Pubchem ID :	7016858

Safety of [ 170564-98-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405
Class:	8
UN#:	3259
Packing Group:	Ⅲ

Computational Chemistry of [ 170564-98-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	44.89
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.51
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	0.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.74
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.	1.26
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	1.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.06

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.29
Solubility	7.72 mg/ml ; 0.0511 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.	-1.03
Solubility	14.1 mg/ml ; 0.0931 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	-2.3
Solubility	0.753 mg/ml ; 0.00498 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.	-6.87 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)	1.25

Application In Synthesis of [ 170564-98-4 ]

* 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 [ 170564-98-4 ]

[ 170564-98-4 ] Synthesis Path-Downstream 1~35

1
[ 406468-05-1 ]
[ 170564-98-4 ]
[ 881853-41-4 ]

References: [1]Tetrahedron Asymmetry,2006,vol. 17,p. 240 - 244.

2
[ 170564-98-4 ]
[ 55309-58-5 ]
2,6-bis[(4R)-4-phenyl-5,6-dihydro-4H-[1,3]oxazinyl]pyridine [ No CAS ]

References: [1]Chemistry - A European Journal,2006,vol. 12,p. 1855 - 1874.

3
[ 37088-67-8 ]
[ 170564-98-4 ]

References: [1]Chemistry - A European Journal,2006,vol. 12,p. 1855 - 1874.

4
[ 5650-41-9 ]
[ 170564-98-4 ]

References: [1]Tetrahedron Asymmetry,2006,vol. 17,p. 240 - 244.

5
[ 6296-54-4 ]
[ 170564-98-4 ]

References: [1]Tetrahedron Asymmetry,2006,vol. 17,p. 240 - 244.

6
[ 14593-04-5 ]
[ 170564-98-4 ]

References: [1]Tetrahedron Asymmetry,2006,vol. 17,p. 240 - 244.

7
[ 170564-98-4 ]
[ 791068-41-2 ]
(S)-3-[(3-hydroxy-1-phenyl-ethylamino)methyl]-1-methyl-1H-quinoxalin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; In dichloromethane; at 20℃; for 16h;	A mixture of 4-methyl-3-oxo-3,4-dihydro-quinoxaline-2-carbaldehyde (0.08 g), sodium cyanoborohydride (0.04 g, 1.5 eq), and (S)-3-AMINO-3-PHENYL-PROPAN-1-OL (65 mg) in dry CHZCLZ (2 mL) was stirred at rt under nitrogen for 16h. The reaction mixture was basified with a sat. NAHCO3 solution, extracted CH2C12. The combined organic extracts were dried (MGS04), filtered and concentrated in vacuo to give a crude oil. FC (CH2C12/MEOH : 9/1) gave the title compound as a yellow oil. LC-MS: Rt = 0.64 min. m/z = 324 (M + 1).

References: [1]Patent: WO2004/96780,2004,A1 .Location in patent: Page 32.

8
[ 115224-13-0 ]
[ 170564-98-4 ]

Yield	Reaction Conditions	Operation in experiment
93%		EXAMPLE 1 Starting compound: (R)-4-Amino-4-phenyl-1-butene Product: (R)-3-Amino-3-phenyl-1-propanol was obtained in a yield of 93% and an enantiomeric excess of 99% White crystals; mp 73-74 C.; 1H-NMR (CDCl3) 1.86 (m, 2H, -CH2CH2OH), 3.76 (t, 2H, -CH2CH2OH), 4.10 (t, 1H, -CH2CH2OH), 7.21-7.35 (m, 5H, Ar-H)
93%		(R)-4-Amino-4-phenyl-1-butene (0.04 mol) was dissolved in 200 ml of methanol in a simple ozonolysis apparatus without gas recycling and was cooled to - 200C. The ozone generator was fed continuously with air, as in example 2. A concentration of 20 g/m3 (ST. P.) of ozone was produced and was completely reactive in the ozonolysis apparatus. After the end of the ozonolysis, the reaction solution was added dropwise over the course of 10 min to 100 ml of an ice-cooled methanolic sodium borohydride solution (0.9 mol/l). The reaction solution was then warmed to room temperature and 10 ml of water were added in order to decompose excess sodium borohydride. After the solvent had been distilled off, the residue was extracted several times with dichloromethane and the combined organic phases were dried over sodium sulfate and filtered. After the solvent had been distilled off, 0.37 mol of (R)-3- amino-3-phenyl-1-propanol (melting point 73-74C) were obtained in 99% enantiomeric excess (93% yield).

References: [1]Patent: WO2005/63682,2005,A1 .Location in patent: Page/Page column 11.
[2]Patent: US2007/123589,2007,A1 .
[3]Patent: WO2008/77769,2008,A1 .Location in patent: Page/Page column 22.

9
[ 170564-98-4 ]
[ 135748-35-5 ]
[ 357434-38-9 ]

Yield	Reaction Conditions	Operation in experiment
15%	In ethyl acetate; N-ethyl-N,N-diisopropylamine;	a 4-Chloro-5-Fluoro-2-[[(1R)-3-Hydroxy-1-Phenylpropyl]Amino]Benzonitrile <strong>[135748-35-5]4-Chloro-2,5-difluorobenzonitrile</strong> (1.0 g, 5.76 mmol) and (gamma1R)-gamma-aminobenzenepropanol (870 mg, 5.76 mmol) were heated in N,N-diisopropylethylamine (740 mg, 5.76 mmol) at 140 C. for 30 h. The reaction mixture was partitioned between ethyl acetate and water and the organic layer separated. The aqueous layer was further extracted with ethyl acetate, and the extracts combined and dried over anhydrous sodium sulphate. The solvent was evaporated and the residue purified by flash chromatography using 10% ethyl acetate/isohexane as eluent to give the title product (260 mg, 15%). MS APCI+vem/z305 ([M+H]+). 1H NMR 300 MHz (CDCl3) 7.33 (5H, m), 7.15 (1H, d), 6.43 (1H, d), 5.98 (1H, d), 4.61 (1H, d), 3.79 (2H, m), 2.11 (2H, m).

References: [1]Patent: US2003/73685,2003,A1 .

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 48 Production of (R)-1-phenyl-3-hydroxypropylamine by Hofmann Rearrangement of (R)-2-phenyl-4-hydroxybutyramide Ten grams of (R)-2-phenyl-4-hydroxybutyramide was dissolved in 250 ml of 0.03 M NaOH and added slowly to a solution 25 grams of bromine in 300 ml of 0.03 M NaOH. The mixture was warmed with stirring until the reddish brown color disappeared. The solution was then cooled, extracted with methyl t-butyl ether*250 ml), and the extracts dried over MgSO4, filtered, and the solvent removed by rotary evaporation. The product (R)-1-phenyl-3-hydroxypropylamine is isolated as a light yellow oil.
		EXAMPLE 50 Production of (R)-1-phenyl-3-hydroxypropylamine by Curtius Rearrangement of (R)-2-phenyl-4-hydroxybutanoic acid hydrazide The hydrazide of (R)-2-phenyl-4-hydroxybutanoic acid (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5 C., followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (R)-1-phenyl-3-hydroxypropylamine is isolated as a light yellow oil.

11
[ 170564-98-4 ]
C₁₇H₁₂N₃O₂PolS₂ [ No CAS ]
C₂₆H₂₅N₄O₃PolS₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6801 - 6805.

12
[ 170564-98-4 ]
[ 1386980-75-1 ]
[ 1386980-32-0 ]

Yield	Reaction Conditions	Operation in experiment
88.5%		Triethylamine (0.021 mL, 0.15 mmol) was added to a mixture of 4-chloro-3-[(2-methoxy-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)-amino]-benzoic acid (0.05 g, 0.13 mmol) (from Example 22 supra) and HATU (0.057 g, 0.15 mmol) (Aldrich) in DMF (2.0 mL). The resultant mixture was stirred at room temperature for 30 minutes. (R)-3-Amino-3-phenylpropan-1-ol (24.2 mg, 0.16 mmol) (Aldrich) was added. The mixture was stirred for 18 hours and then partitioned between ethyl acetate and water. The precipitate was collected by filtration and washed with ethyl acetate and water and dried in vacuum oven to give (R)-N-(2-chloro-5-(3-hydroxy-1-phenylpropylcarbamoyl)phenyl)-2-methoxy-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamide. (Yield 0.06 g, 88.5%).HR-MS (ES+) m/z Calculated for C25H23ClN5O5 ([M+H]+): 508.1382. Found: 508.1383

References: [1]Patent: US2012/184542,2012,A1 .Location in patent: Page/Page column 85.

13
[ 170564-98-4 ]
[ 1386981-92-5 ]

References: [1]Patent: US2012/184542,2012,A1 .

14
[ 170564-98-4 ]
[ 1386981-94-7 ]

References: [1]Patent: US2012/184542,2012,A1 .

15
[ 170564-98-4 ]
[ 1386981-96-9 ]

References: [1]Patent: US2012/184542,2012,A1 .

16
[ 170564-98-4 ]
[ 22509-74-6 ]
[ 644961-00-2 ]