21911-84-2|Methyl 3-(phenylamino)propanoate| Ambeed

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Quality Control of [ 21911-84-2 ] Purity: 98% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of [ 21911-84-2 ]

CAS No. :	21911-84-2
Formula :	C₁₀H₁₃NO₂
M.W :	179.22
SMILES Code :	C1=CC=CC=C1NCCC(=O)OC
MDL No. :	MFCD00089334
InChI Key :	TWAMXXLZDQNMCF-UHFFFAOYSA-N
Pubchem ID :	89103

Safety of [ 21911-84-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 21911-84-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	5
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	51.45
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.09
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	2.28
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.47
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.	1.67
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	1.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.82

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.4
Solubility	0.715 mg/ml ; 0.00399 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.	-2.72
Solubility	0.34 mg/ml ; 0.0019 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	-3.33
Solubility	0.0832 mg/ml ; 0.000465 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	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	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.	-5.77 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)	1.11

Application In Synthesis of [ 21911-84-2 ]

* 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 [ 21911-84-2 ]

[ 21911-84-2 ] Synthesis Path-Downstream 1~35

1
[ 75-21-8 ]
[ 21911-84-2 ]
[ 70817-88-8 ]

References: [1]Patent: US2470094,1945, .

2
[ 553-90-2 ]
[ 21911-84-2 ]
[ 65126-04-7 ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 2532,2537.

3
[ 21911-84-2 ]
[ 27139-02-2 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 5957,5959.

4
[ 21911-84-2 ]
[ 98-88-4 ]
[ 24364-35-0 ]

References: [1]Journal of the Chemical Society,1957,p. 4166,4170.
Journal of the Chemical Society,1958,p. 3377,3379.

5
[ 21911-84-2 ]
[ 75-36-5 ]
[ 99855-42-2 ]

References: [1]Journal of the Chemical Society,1957,p. 4166,4170.
Journal of the Chemical Society,1958,p. 3377,3379.

6
[ 292638-85-8 ]
[ 62-53-3 ]
[ 21911-84-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With ionic liquid [bmim]BF4 stabilized magnetic cobalt nanoparticles; In neat (no solvent); at 20℃; for 0.75h;	General procedure: 1mmol of amine or thiol and 1mmol of activated alpha,beta-unsaturated compound (Michael acceptor) were stirred together in the presence of 5mol% (0.1mmol) of stabilized cobalt nanoparticles for an appropriate time (Scheme1). Following the completion of the reaction as indicated by TLC (hexane: ethyl acetate), dichloromethane was added to the reaction mixture and the cobalt catalyst was recovered by applying a magnetic field and decanting rest of the reaction mixture into another flask from where solvent was evaporated off and final product was isolated. Further purification was carried out by column chromatography on silica gel using ethyl acetate/petroleum ether as eluent. Structural assignments of the products were done based on their 1H NMR, 13C NMR and mass spectroscopic analysis.
93%	With Ps-AlCl3; at 70℃; for 2.5h;	General procedure: In a typical experiment, a mixture of amine (11 mmol), methacrylate or acrylonitrile (2 mmol), and Ps-AlCl3 (0.53 g, 0.24 mmol AlCl3 for aromatic amines; 0.27 g, 0.12 mmol AlCl3 for aliphatic amines) was stirred at 70 C for aromatic amines, room temperature for aliphatic amines. After completion of the reaction, Ps-AlCl3 was filtered and washed with ethyl acetate (3 10 ml), dried, and used in the next run under the same reaction conditions. The filtrate was concentrated to give the crude product, which was purified further by column chromatography (petroleum ether/ethylacetate or methanol/ethyl acetate).
92%	With OMS-MIL-100(Fe); In toluene; at 50℃; for 24h;Sealed tube; Schlenk technique; Green chemistry;	General procedure: To a Schlenk line sealed tube charged with amine (1mmol),alpha,beta-unsaturated compound (1.2mmol) in 4ml of dry toluene,MIL-100(Fe) (3mol%) was added under stirring condition.The mixture was then stirred for a certain time at 50C.The progress of reaction was monitored by TLC. After completionof the reaction, the catalyst was completely recoveredfrom the residue by centrifuge, and the product was extractedfrom reaction mixture with ethyl acetate and H2O/2M HCl. The organic phase was evaporated under reduced pressureand the reaction mixture was then subjected to column chromatography(n-hexane:ethyl acetate = 4:1, V/V) to give thecorresponding aza-Michael products. All products and characterizedby comparison of their physical properties, 1H and13C spectra with those of already reported [17, 39, 40].

88%	With Imidazole hydrochloride; In neat (no solvent); at 100℃; for 2h;Green chemistry;	General procedure: The 1 (5.0 mmol) and 2 (6.5 mmol) in a molar ratio of 1:1.3 reacted with stirring in the presenceof imidazolium hydrochloride (1.5 mmol, 0.3 eq). Heating was performed using an oil bath and thereaction was followed up by TLC until completion. After completion of the reaction, the system wascooled. The organic layer was extracted using water (15 mL) and ethyl acetate (20 mL) and driedusing anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue wassubjected to column chromatography eluting with petroleum ether: ethyl acetate (7:1) mixtures.
85%	With polyacrylamide coated magnetite (PAM(at)MNP); In neat (no solvent); at 65℃; for 4h;	General procedure: Aniline (1mmol), methyl acrylate (1.5mmol), and catalyst (100mg) were placed into a round bottom flask and stirred at 60C for 4h. The progress of the reaction was monitored with thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and the catalyst was recovered by an external magnet. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography. Conversion of the substrates and selectivity of the products was determined by GCMS. The recovered catalyst was dried at 50C for 2h and can be reused for recycling experiments.
12%	With acetic acid; at 79℃;	Aniline (Acros; 59.89 mL, 657 mmol), Methylacrylate (Acros; 62.54 mL, 690 mmol) and Glacial acetic acid (15 mL) and were combined and heated at 79 C. overnightThe reaction mixture was cooled to room temperature and added to ice water, a solid precipitated and was filtered off and dissolved in dichloromethane aliquot taken and pre-absorbed onto silica and purified by vacuum filtration chromatography eluting with DCM. Product containing fractions were combined and evaporated to give the title compound as a pale yellow sticky solid (14.33 g, 12%)1H NMR (399.9 MHz, DMSO-D6): deltaH, 2.57 (tr, 2H), 3.29 (tr, 2H), 3.61 (s, 3H), 5.57 (tr, 1H), 6.55 (m, 3H), 7.08 (m, 1H); MS m/z 180 [M+H]+.
	With Pseudomonas fluorescence lipase immobilized on hyroxypropyl methyl cellulose support; In toluene; at 50℃; for 3h;Enzymatic reaction;	General procedure: Various beta-amino ester moieties were synthesized in a 10 mL glass reaction vessel of 1.2 cm i.d. with a glass lid. The desired Michael acceptor was taken into a reaction vessel and diluted by solvent. Afterwards, Michael donor was added into the reaction vessel and reaction was initiated by addition of immobilized HMC:PFL lipase very soon at a specified temperature. The sample of reaction mixture was analyzed by using gas chromatograph (Perkin Elmer Clarus: 400) having flame ionizing detector (FID) and capillary column. The detector and injector temperature were kept 280 and 50 C, respectively. The oven temperature of GC was kept at 50 C for 3 min constant and after that raised with 10 C/min up to the 280 C. Moreover, reaction products were also verified by GCMS (Gas-Chromatography-Mass Spectroscopy Shimadzu QP-2010) analysis.

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7
[ 21911-84-2 ]
[ 98-09-9 ]
[ 101090-64-6 ]

References: [1]Journal of the Chemical Society,1957,p. 4166,4170.
Journal of the Chemical Society,1958,p. 3377,3379.

8
[ 21911-84-2 ]
[ 98-59-9 ]
[ 17266-98-7 ]

References: [1]Organic Preparations and Procedures International,2013,vol. 45,p. 28 - 43.
[2]Journal of the American Chemical Society,1949,vol. 71,p. 1901,1905.
[3]European Journal of Medicinal Chemistry,1993,vol. 28,p. 837 - 852.

9
[ 21911-84-2 ]
[ 75-56-9 ]
N-(2-hydroxy-propyl)-N-phenyl-β-alanine methyl ester [ No CAS ]

References: [1]Patent: US2470094,1945, .

10
[ 21911-84-2 ]
[ 32184-10-4 ]
[ 18042-81-4 ]