[ CAS No. 866028-26-4 ] {[proInfo.proName]}

Name: 866028-26-4|Ethyl 2-(2-chlorobenzyl)acrylate|97%
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SKU: A601441
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Quality Control of [ 866028-26-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 866028-26-4 ]

SDS Specification

Alternatived Products of [ 866028-26-4 ]

Product Details of [ 866028-26-4 ]

CAS No. :	866028-26-4	MDL No. :	MFCD27930542
Formula :	C₁₂H₁₃ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VTAOWWAFBSFWSG-UHFFFAOYSA-N
M.W :	224.68	Pubchem ID :	69150705
Synonyms :		Chemical Name :	Ethyl 2-(2-chlorobenzyl)acrylate

Calculated chemistry of [ 866028-26-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.26
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.83
Log Po/w (XLOGP3) :	3.63
Log Po/w (WLOGP) :	3.0
Log Po/w (MLOGP) :	3.31
Log Po/w (SILICOS-IT) :	3.62
Consensus Log Po/w :	3.28

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.49
Solubility :	0.0734 mg/ml ; 0.000327 mol/l
Class :	Soluble
Log S (Ali) :	-3.87
Solubility :	0.0303 mg/ml ; 0.000135 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.35
Solubility :	0.00997 mg/ml ; 0.0000444 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.04

Safety of [ 866028-26-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 866028-26-4 ]

* 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.

Upstream synthesis route of [ 866028-26-4 ]
Downstream synthetic route of [ 866028-26-4 ]

[ 866028-26-4 ] Synthesis Path-Upstream 1~4

1
[ 50-00-0 ]
[ 866028-25-3 ]
[ 866028-26-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In water at 20 - 90℃; for 6 h;	To a stirred mixture of ethyl 3- (2-chlorophenyl)-2- (diethoxyphosphoryl) propanoate (step 1,14. 6 g, 41.9 mmol) and 37percent formaldehyde in water (20 mL) was added a solution of potassium carbonate (17.4 g) in water (80 mL) at the room temperature and the mixture was stirred for 6 h at 90 °C. After cooling to room temperature, the mixture was extracted with diethyl ether (300 mL), and then the organic layer was washed with brine (100 mL), dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (300 g) eluting with hexane/ethyl acetate (30/1) to afford 6.57 g (70percent) of the title compound as a colorless oil: 1H-NMR (CDC13) S 7.39-7. 36 (1H, m), 7.25-7. 16 (3H, m), 6.27 (1H, q, J=1.3 Hz), 5.33 (1H, q, J=1.7 Hz), 4.22 (2H, q, J=7.2 Hz), 3.76 (2H, t, J=1.4 Hz), 1.29 (3H, t, J=6.0 Hz).
70%	With potassium carbonate In water at 20 - 90℃; for 6 h;	To a stirred mixture of ethyl 3-(2-chlorophenyl)-2-(diethoxyphosphoryl)propanoate (step 1 , 14.6 g,41.9 mmol) and 37percent formaldehyde in water (20 mL) was added a solution of potassium carbonate (17.4 g) in water (80 mL) at room temperature and the mixture was stirred for 6 hours at 90 ⁰C. After cooling to room temperature, the mixture was extracted with diethyl ether (300 mL), and then the organic layer was washed with brine (100 mL), dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (300 g), eluting with hexane/ethyl acetate (30/1 ), to afford 6.57 g (70percent) of the title compound as a colorless oil:¹H-NMR (CDCI₃) δ 7.39-7.36 (1 H, m), 7.25-7.16 (3H, m), 6.27 (1 H, q, J=1.3 Hz), 5.33 (1 H, q, J=1.7 Hz), 4.22 (2H, q, J=7.2 Hz), 3.76 (2H, t, J=1.4 Hz), 1.29 (3H, t, J=6.0 Hz).

Reference： [1] Patent: WO2005/92858, 2005, A2, . Location in patent: Page/Page column 90
[2] Patent: WO2006/134485, 2006, A1, . Location in patent: Page/Page column 34
[3] ChemMedChem, 2016, p. 1790 - 1803

2
[ 682813-61-2 ]
[ 866028-26-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3656 - 3671

3
[ 611-17-6 ]
[ 866028-26-4 ]

Reference： [1] ChemMedChem, 2016, p. 1790 - 1803

4
[ 88039-46-7 ]
[ 866028-26-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3656 - 3671

[ 866028-26-4 ] Synthesis Path-Downstream 1~17

1
[ 50-00-0 ]
[ 866028-25-3 ]
[ 866028-26-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In water; at 20 - 90℃; for 6.0h;	To a stirred mixture of ethyl 3- (2-chlorophenyl)-2- (diethoxyphosphoryl) propanoate (step 1,14. 6 g, 41.9 mmol) and 37% formaldehyde in water (20 mL) was added a solution of potassium carbonate (17.4 g) in water (80 mL) at the room temperature and the mixture was stirred for 6 h at 90 C. After cooling to room temperature, the mixture was extracted with diethyl ether (300 mL), and then the organic layer was washed with brine (100 mL), dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (300 g) eluting with hexane/ethyl acetate (30/1) to afford 6.57 g (70%) of the title compound as a colorless oil: 1H-NMR (CDC13) S 7.39-7. 36 (1H, m), 7.25-7. 16 (3H, m), 6.27 (1H, q, J=1.3 Hz), 5.33 (1H, q, J=1.7 Hz), 4.22 (2H, q, J=7.2 Hz), 3.76 (2H, t, J=1.4 Hz), 1.29 (3H, t, J=6.0 Hz).
70%	With potassium carbonate; In water; at 20 - 90℃; for 6.0h;	To a stirred mixture of ethyl 3-(2-chlorophenyl)-2-(diethoxyphosphoryl)propanoate (step 1 , 14.6 g,41.9 mmol) and 37% formaldehyde in water (20 mL) was added a solution of potassium carbonate (17.4 g) in water (80 mL) at room temperature and the mixture was stirred for 6 hours at 90 0C. After cooling to room temperature, the mixture was extracted with diethyl ether (300 mL), and then the organic layer was washed with brine (100 mL), dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (300 g), eluting with hexane/ethyl acetate (30/1 ), to afford 6.57 g (70%) of the title compound as a colorless oil:1H-NMR (CDCI3) delta 7.39-7.36 (1 H, m), 7.25-7.16 (3H, m), 6.27 (1 H, q, J=1.3 Hz), 5.33 (1 H, q, J=1.7 Hz), 4.22 (2H, q, J=7.2 Hz), 3.76 (2H, t, J=1.4 Hz), 1.29 (3H, t, J=6.0 Hz).

Reference： [1]Patent: WO2005/92858,2005,A2 .Location in patent: Page/Page column 90
[2]Patent: WO2006/134485,2006,A1 .Location in patent: Page/Page column 34
[3]ChemMedChem,2016,p. 1790 - 1803

2
[ 866028-26-4 ]
[ 917242-98-9 ]
ethyl 2-(2-chlorobenzyl)-3-(6'-fluoro-3',4'-dihydro-8H-spiro[8-azabicyclo[3.2.1]octane-3,1'-isochromen]-8-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.3%	In ethanol; at 25℃; for 120.0h;	A solution of e'-fluoro-S'^'-dihydrospirobeta-azabicycIotS^.IJoctane-Sji '-isochromene] (step 4 of example 6, 683.1 mg, 2.76 mmol) and <strong>[866028-26-4]ethyl 2-(2-chlorobenzyl)acrylate</strong> (step 2, 564.2 mg, 2.51 mmol) in EPO <DP n="37"/>ethanol (2.0 mL) was stirred at 25 0C for 5 days. The reaction mixture was concentrated in vacuo to give brown syrup. The residue was purified by column chromatography on silica gel, eluting with hexane/ethyl acetate (6/1 ), to give the title product which contained a small amount of impurity. Then, the product was further purified by preparative TLC on silica gel, developing with CH2CI2/Me0H (60/1 ), to afford 476.9 mg (40.3%) of the title compound as a colorless oil:1H-NMR (300MHz, CDCI3, ppm) delta 7.38-7.32 (1 H, m), 7.27-7.24 (1 H, m), 7.20-7.13 (2H, m), 7.04 (1 H, dd, J=8.8 Hz, 6.0 Hz), 6.83 (1 H, ddd, J=8.8 Hz, 8.8 Hz, 2.9 Hz), 6.75 (1 H, dd, J=8.8 Hz, 2.9 Hz), 4.09 (2H, q, J=7.3 Hz), 3.81 (2H, t, J=5.1 Hz), 3.30-3.19 (3H, m), 3.02-2.89 (2H, m), 2.75-2.68 (3H, m), 2.89-2.53 (1 H, m), 2.11-1.76 (8H, m), 1.17 (3H, t, J=7.3 Hz); MS (ESI positive) m/z: 472 (M + H)+.

Reference： [1]Patent: WO2006/134485,2006,A1 .Location in patent: Page/Page column 34-35

3
[ 611-17-6 ]
[ 866028-26-4 ]