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[ CAS No. 49562-28-9 ] {[proInfo.proName]}

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Chemical Structure| 49562-28-9
Chemical Structure| 49562-28-9
Structure of 49562-28-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 49562-28-9 ]

CAS No. :49562-28-9 MDL No. :
Formula : C20H21ClO4 Boiling Point : -
Linear Structure Formula :- InChI Key :YMTINGFKWWXKFG-UHFFFAOYSA-N
M.W : 360.83 Pubchem ID :3339
Synonyms :
NSC-281319
Chemical Name :Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Calculated chemistry of [ 49562-28-9 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.3
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 97.98
TPSA : 52.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.64
Log Po/w (XLOGP3) : 5.17
Log Po/w (WLOGP) : 4.68
Log Po/w (MLOGP) : 3.54
Log Po/w (SILICOS-IT) : 4.95
Consensus Log Po/w : 4.4

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.23
Solubility : 0.00214 mg/ml ; 0.00000592 mol/l
Class : Moderately soluble
Log S (Ali) : -6.02
Solubility : 0.000344 mg/ml ; 0.000000953 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.51
Solubility : 0.000112 mg/ml ; 0.00000031 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.64

Safety of [ 49562-28-9 ]

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 [ 49562-28-9 ]

* 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.

  • Upstream synthesis route of [ 49562-28-9 ]
  • Downstream synthetic route of [ 49562-28-9 ]

[ 49562-28-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 49562-28-9 ]
  • [ 42017-89-0 ]
YieldReaction ConditionsOperation in experiment
15%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuranReflux
Stage #2: With hydrogenchloride In tetrahydrofuran; water
Example 12 - Formula 139 - Compounds 12a 12bIntermediate B: 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid To a stirred solution of compound A (1 .0 g, 2.77 mmol) in THF (10 mL) was added LiOH-H&20 (0.7 g, 16.6 mmol) and H20 (10 mL). The resulting mixture was heated at reflux overnight then quenched with a 1 M aqueous HCI solution and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine, dried over MgS04 and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH, 15/1 , v/v) to give 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (130 mg, 15percent) as a white solid.LC-MS (Agilent): Rt 3.00 min; m/z calculated for Ci7H15CI04 [M+H]+ 319.07, found 319.1 .
15% With lithium hydroxide monohydrate; water In tetrahydrofuranReflux To a stirred solution of compound A (1.0 g, 2.77 mmol) in THF (10 mL) was added LiOH.H2O (0.7 g, 16.6 mmol) and H2O (10 mL).
The resulting mixture was heated at reflux overnight then quenched with a 1 M aqueous HCl solution and extracted with EtOAc (10 mL*3).
The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure.
The residue was purified by flash chromatography (CH2Cl2/MeOH, 15/1, v/v) to give 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (130 mg, 15percent) as a white solid.
LC-MS (Agilent): Rt 3.00 min; m/z calculated for C17H15ClO4 [M+H]+ 319.07. found 319.1.
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 14, p. 2497 - 2499
[2] Acta Crystallographica Section C: Crystal Structure Communications, 2005, vol. 61, # 2, p. o81-o84
[3] Patent: WO2012/63085, 2012, A2, . Location in patent: Page/Page column 83-84
[4] Patent: US2013/225594, 2013, A1, . Location in patent: Paragraph 0268; 0269
[5] Photochemistry and Photobiology, 2002, vol. 75, # 3, p. 193 - 200
[6] Biochemical Pharmacology, 2004, vol. 67, # 2, p. 285 - 292
[7] Farmaco, 2005, vol. 60, # 5, p. 425 - 438
[8] Crystal Growth and Design, 2014, vol. 14, # 8, p. 3800 - 3812
[9] Drug Metabolism and Disposition, 2015, vol. 43, # 11, p. 1815 - 1822
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