14062-29-4|Ethyl 2-(3-chlorophenyl)acetate| Ambeed

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Quality Control of [ 14062-29-4 ] Purity: 98% SDS Specification

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Product Details of [ 14062-29-4 ]

CAS No. :	14062-29-4
Formula :	C₁₀H₁₁ClO₂
M.W :	198.65
SMILES Code :	CCOC(=O)CC1=CC(Cl)=CC=C1
MDL No. :	MFCD07787498

Safety of [ 14062-29-4 ]

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

Computational Chemistry of [ 14062-29-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	52.12
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.61
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	2.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.45
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.	2.84
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	3.03
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.9
Solubility	0.25 mg/ml ; 0.00126 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.	-2.99
Solubility	0.204 mg/ml ; 0.00103 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	-3.9
Solubility	0.0248 mg/ml ; 0.000125 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.	-5.54 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)	1.64

Application In Synthesis of [ 14062-29-4 ]

* 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 [ 14062-29-4 ]

[ 14062-29-4 ] Synthesis Path-Downstream 1~35

1
[ 64-17-5 ]
[ 1529-41-5 ]
[ 14062-29-4 ]

References: [1]Journal of the Chemical Society,1954,p. 3263,3268.

2
[ 14062-29-4 ]
[ 141-43-5 ]
(3-chloro-phenyl)-acetic acid-(2-hydroxy-ethylamide) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 2837,2842.
[2]Patent: US2479295,1946, .

3
[ 4360-47-8 ]
[ 14062-29-4 ]
[ 134823-34-0 ]
[ 134823-34-0 ]

References: [1]European Journal of Medicinal Chemistry,1991,vol. 26,p. 19 - 32.
[2]European Journal of Medicinal Chemistry,1991,vol. 26,p. 19 - 32.

4
[ 103-36-6 ]
[ 58357-84-9 ]
[ 621-79-4 ]
[ 14062-29-4 ]
[ 77418-76-9 ]

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1605 - 1607.

5
[ 64-17-5 ]
[ 7023-78-1 ]
[ 14062-29-4 ]

References: [1]Journal of Organometallic Chemistry,1991,vol. 409,p. 385 - 409.

6
[ 6048-06-2 ]
[ 58357-84-9 ]
[ 14062-29-4 ]
[ 18166-64-8 ]
[ 77418-81-6 ]

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1605 - 1607.

7
[ 14062-29-4 ]
[ 41024-33-3 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 481 - 490.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3535 - 3539.
[3]Organic Letters,2018,vol. 20,p. 1832 - 1836.

8
[ 20511-20-0 ]
[ 58357-84-9 ]
[ 14062-29-4 ]
[ 18254-00-7 ]
[ 77418-86-1 ]

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1605 - 1607.

9
[ 14062-29-4 ]
[ 67-64-1 ]
[ 82129-59-7 ]

References: [1]Heterocycles,1983,vol. 20,p. 2189 - 2195.

Yield	Reaction Conditions	Operation in experiment
77%	With copper(II) bis(trifluoromethanesulfonate); triethylamine; In N,N-dimethyl acetamide; at 20℃;Sealed tube;	General procedure: General Procedure A: Cu(OTf)2 (54.3 mg, 0.150 mmol, 0.30 equiv.) and arylboronic ester (1.00 mmol, 1.20 to 2.00 equiv.) were added sequentially to a 1 dram vial charged with a stirbar. The carboxylic acid (0.500 mmol, 1.00 equiv.) was added as a solution in anhydrous DMA (0.6 mL). Additional DMA (2×0.3 mL) was used to quantitatively transfer the solution to the reaction mixture. The solution was stirred until a homogeneous pale blue solution was formed (approximately 2 minutes, partially heterogeneous mixtures obtained when using increased Cu loadings), followed by the addition of triethylamine (0.42 mL, 3.0 mmol, 6.0 equiv.). The vial was sealed with a PTFE-lined cap, exposed to air via a needle, and gently stirred at room temperature. Upon completion of the reaction (24 to 72 h), the reaction mixture was diluted with EtOAc (40 mL), and washed sequentially with NH4Cl (15 mL), 0.5 M NaOH (2×20 mL), and brine (15 mL). The organic layer was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography. No difference was observed if reactions were prepared in an atmosphere-controlled glovebox, then exposed to ambient air.

12
[ 1878-65-5 ]
[ 14062-29-4 ]

Yield	Reaction Conditions	Operation in experiment
86.8%	sulfuric acid; In ethanol;	EXAMPLE 6 2-(3-Chloro-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (3-Chloro-phenyl)-acetic acid (6.03 g, 0.03 mol) was dissolved in ethanol (37.7 mL) and treated with a catalytic amount of sulfuric acid. The reaction mixture was refluxed for 12 h. The reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded (3-chloro-phenyl)-acetic acid ethyl ester (6.10 g, 86.8%) as a clear oil: EI-HRMS m/e calcd for C10H11ClO2 (M+) 198.0448, found 198.0442.
86.8%	sulfuric acid; In ethanol;	EXAMPLE 6 2-(3-Chloro-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (3-Chloro-phenyl)-acetic acid (6.03 g, 0.03 mol) was dissolved in ethanol (37.7 mL) and treated with a catalytic amount of sulfuric acid. The reaction mixture was heated under reflux for 12 h. The reaction was concentrated in. vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded (3-chloro-phenyl)-acetic acid ethyl ester (6.10 g, 86.8%) as a clear oil: EI-HRMS m/e calcd for C10H11ClO2 (M+) 198.0448, found 198.0442.

References: [1]Patent: US2001/39344,2001,A1 .
[2]Patent: US6610846,2003,B1 .

13
[ 63503-60-6 ]
[ 105-36-2 ]
[ 14062-29-4 ]

References: [1]Chemical Communications,2001,p. 669 - 670.

14
[ 64-17-5 ]
[ 1878-65-5 ]
[ 14062-29-4 ]

References: [1]Chemical Communications,2015,vol. 51,p. 15446 - 15449.
[2]Tetrahedron Letters,2003,vol. 44,p. 331 - 334.
[3]European Journal of Organic Chemistry,2013,p. 4255 - 4261.
[4]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605.
[5]Journal of Medicinal Chemistry,2010,vol. 53,p. 3618 - 3625.
[6]Journal of Organic Chemistry,2009,vol. 74,p. 5100 - 5103.
[7]Chinese Journal of Chemistry,2010,vol. 28,p. 605 - 612.

15
[ 14062-29-4 ]
[ 109-94-4 ]
[ 200215-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In diethyl ether; at 0 - 20℃;	General procedure: To a solution of ester 8 (20 mmol) in anhydrous ethyl ether was added ethyl formate (3.2 mL,40 mmol) at 0oC. Then sodium (0.92 g, 40 mmol) was added slowly. The reaction mixture wasstirred at room temperature. After completion of the reaction, the mixture was poured into icewater and extracted with Et2O (3×30 mL). The aqueous phase was acidified with a solution of 2NHCl to PH 3. Followed an extraction with Et2O (3×30 mL) and the organic layers were combined,dried over Na2SO4, filtered and concentrated in vacuum, leading to aldehyde 9 as a yellow oil which was used in the next step without further purification. Then 9 was dissolved in anhydrousdichloromethane and p-methoxyaniline (2.95 g, 24 mmol) was added, the reaction mixture wasstirred overnight at room temperature, the solvent was evaporated and the residue was subjected tochromatography to afford -enamino ester 1.

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4735 - 4739.
[2]Synlett,2014,vol. 25,p. 1879 - 1882.

16
[ 894421-72-8 ]
[ 14062-29-4 ]
3-(1-benzyl-5-p-tolyl-1H-pyrazol-3-yl)-2-(3-chloro-phenyl)-propionic acid ethyl ester [ No CAS ]