22744-12-3|2-(4-(Methoxycarbonyl)phenyl)acetic acid| Ambeed

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Quality Control of [ 22744-12-3 ] Purity: 98% SDS Specification

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Product Details of [ 22744-12-3 ]

CAS No. :	22744-12-3
Formula :	C₁₀H₁₀O₄
M.W :	194.18
SMILES Code :	O=C(O)CC1=CC=C(C(OC)=O)C=C1
MDL No. :	MFCD19440718
InChI Key :	TXZVCDJZNRCDKW-UHFFFAOYSA-N
Pubchem ID :	10797879

Safety of [ 22744-12-3 ]

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

Computational Chemistry of [ 22744-12-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	49.27
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.62
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	1.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.1
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.	1.55
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	1.47
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.09
Solubility	1.59 mg/ml ; 0.0082 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.	-2.52
Solubility	0.592 mg/ml ; 0.00305 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	-2.26
Solubility	1.08 mg/ml ; 0.00555 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.	-6.37 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.	0.56

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)	1.44

Application In Synthesis of [ 22744-12-3 ]

* 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 [ 22744-12-3 ]

[ 22744-12-3 ] Synthesis Path-Downstream 1~35

1
[ 5440-00-6 ]
[ 22744-12-3 ]
[ 101092-80-2 ]

References: [1]Chemicke Zvesti,1958,vol. 12,p. 519,521.
Chem.Abstr.,1959,p. 3232.

2
[ 22744-13-4 ]
[ 22744-12-3 ]

References: [1]Chemicke Zvesti,1958,vol. 12,p. 519,521.
Chem.Abstr.,1959,p. 3232.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8590 - 8598.

3
[ 52787-14-1 ]
[ 22744-12-3 ]

Yield	Reaction Conditions	Operation in experiment
94.4%	With lithium hydroxide monohydrate; water; In tetrahydrofuran; ethanol; at 25℃; for 10h;	2- (4- (methoxycarbonyl) phenyl) acetic acid (58,24.04 dirty 1) to the reaction flask, 31111 water, 31111 5ml tetrahydrofuran and a mixed solvent of ethanol raw materials were dissolved. Was then added Eta0Eta-Eta20 (1.068,25.24pipiomicron1) alpha25 C was stirred for 10 hours the reaction is substantially complete. The solution was spin-off in tetrahydrofuran and ethanol, followed by addition of 26ml of dilute hydrochloric acid (lmmol / L), and a white precipitate formed, suction, infrared drying to give a white solid 4.4g, 94.4% yield
83%	With potassium carbonate; In methanol; water; at 20℃; for 4h;	A solution of methyl 4- (2-methoxy-2-oxoethyl) benzoate 26, (800 mg, 3.85 ramol) and K2CO3 (929 mg, 5.67 mmol) in water/methanol mixture (20 mL, 1:1) was stirred at room temperature 4 hrs. After concentrating the reaction mixture to 5 mL diluted with water (20 mL) . Then the aqueous layer was washed with dichloromethane (20 mL chi 2), and acidified to pH~3 with 12M HC1. The aqueous solution was extracted with ethyl acetate (20 mL * 2) . Organics was combined, dried over NaaSOi and evaporated in vacuo to give titled compound 27. (620 mg, 83%). NMR (CHCI3, 400 MHz): delta 7.90 (d, J=8.1 Hz, 1H), 7.42 (d, J=8.1, 1H) , 3.85 (s, 3H) , 3.68 (s, 2H) ; [M+H]+ = 195.4 (APCI+) .
80%	With hydrogenchloride; In methanol; at 20 - 50℃; for 28h;	Step 2: 2-(4-(Methoxycarbonyl)phenyl)acetic Acid A stirred solution of methyl 4-(cyanomethyl)benzoate (22.0 g, 0.125 mol) in methanol (550 mL) was bubbled through with hydrogen chloride gas for 8 h under reflux conditions. The reaction mixture was cooled to 20 C., stirred for an additional 24 h and filtered. The filtrate was evaporated under reduced pressure. The resultant residue was dissolved in diethyl ether, washed sequentially with water and saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and evaporated to afford the methyl ester as a solid residue. 1H NMR (400 MHz, CDCl3): 8.00 (d, J=8 Hz, 2H); 7.35 (d, J=8.4 Hz, 2H); 3.91 (s 3H); 3.70 (s, 3H); 3.68 (s, 2H). GCMS: 209 (M+H). The methyl ester (8.21 g, 0.039 mmol) was dissolved in methanol, treated with sodium hydroxide (1.58 g, 0.039 mol), heated to 50 C., stirred for 4 h, cooled to room temperature, stirred for an additional 24 h and concentrated in vacuo. The resultant residue was partitioned between diethyl ether and water. The aqueous layer was acidified with concentrated HCl. The resultant precipitate was removed by filtration and dried overnight, under vacuum, to afford 2-(4-(methoxycarbonyl)phenyl)-acetic acid (80%) as an off-white solid. 1H NMR (400 MHz, DSMO-d6): 7.90 (d, J=8 Hz, 2H); 7.422 (d, J=8 Hz, 2H); 3.85 (s 3H) 3.68 (s, 2H). [M+H] 195

64.4%	With potassium carbonate; In methanol; water; at 20℃; for 1.5h;	Methyl 4-(2-methoxy-2-oxoethyl)benzoate (100 mg, 0.48 mmol), methanol (1.5 mL), water (1.5 mL) and anhydrous potassium carbonate (116 mg, 0.72 mmol) were added in a 10 mL single-neck flask, and the mixture was stirred at room temperature for 1.5 hours. After the materials had all reacted when being determined by TLC, solvent was removed in vacuo, and the residue was redissolved in ethyl acetate (1 mL) and separated by preparative thin layer chromatography (petroleum ether: ethyl acetate = 1:1) to give a product (white solid, 60 mg), with a yield of 64.4%. 1H NMR (400 MHz, CDCl3) delta 8.00 (d, J = 8.1 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 3.91 (s, 3H), 3.70 (s, 2H).
	With lithium hydroxide; In tetrahydrofuran; methanol; water;	iv. 4-Methoxycarbonylphenylacetic acid. To a solution of methyl 4-methoxycarbonylphenylacetate (3.15 g) dissolved in tetrahydrofuran (100 mL), methanol (25 mL) and water (25 mL) at 0 C. was added lithium hydroxide (0.7 g) and the solution was allowed to stir for 2 h. The solution was acidified to pH 2.5 and the product extracted into ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give an oil which was crystallized from hexane to give the mono-acid; TLC: Rf =0.65, methanol:dichloromethane (20:80); MS: m/z=195(M+1).
		A stirred solution of methyl 4-(cyanomethyl)benzoate (22.0 g, 0.125 mol) in methanol (550 mL) was bubbled through with hydrogen chloride gas for 8 h under reflux conditions. The reaction mixture was cooled to 20 C., stirred for an additional 24 h and filtered. The filtrate was evaporated under reduced pressure. The resultant residue was dissolved in diethyl ether, washed sequentially with water and saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and evaporated to afford the methyl ester as a solid residue. 1H NMR (400 MHz, CDCl3): 8.00 (d, J=8 Hz, 2H); 7.35 (d, J=8.4 Hz, 2H); 3.91 (s 3H); 3.70 (s, 3H); 3.68 (s, 2H). GCMS: 209 (M+H). The methyl ester (8.21 g, 0.039 mmol) was dissolved in methanol, treated with sodium hydroxide (1.58 g, 0.039 mol), heated to 50 C., stirred for 4 h, cooled to room temperature, stirred for an additional 24 h and concentrated in vacuo. The resultant residue was partitioned between diethyl ether and water. The aqueous layer was acidified with concentrated HCl. The resultant precipitate was removed by filtration and dried overnight, under vacuum, to afford 2-(4-(methoxycarbonyl)phenyl)-acetic acid (80%) as an off-white solid. 1H NMR (400 MHz, DSMO-d6): 7.90 (d, J=8 Hz, 2H); 7.422 (d, J=8 Hz, 2H); 3.85 (s 3H) 3.68 (s, 2H). [M+H] 195

References: [1]Patent: CN105541777,2016,A .Location in patent: Paragraph 0015; 0062; 0063; 0064.
[2]Journal of the Indian Chemical Society,1987,vol. 64,p. 34 - 37.
[3]Patent: WO2015/100363,2015,A1 .Location in patent: Page/Page column 53.
[4]Patent: US2007/219240,2007,A1 .Location in patent: Page/Page column 31.
[5]Journal of Medicinal Chemistry,1998,vol. 41,p. 5219 - 5246.
[6]Patent: EP3581561,2019,A1 .Location in patent: Paragraph 0127; 0129.
[7]Chimica therapeutica,1973,vol. 8,p. 487 - 494.
[8]Patent: US5521179,1996,A .
[9]Patent: US2009/23707,2009,A1 .Location in patent: Page/Page column 26-27.

4
[ 22744-12-3 ]
[ 119435-90-4 ]
[ 119435-91-5 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1098 - 1108.

5
[ 872-32-2 ]
[ 22744-12-3 ]
[4-(pyrrolidin-2-ylidene-acetyl)-phenyl]-acetic acid [ No CAS ]

References: [1]Journal fur Praktische Chemie - Chemiker-Zeitung,1998,vol. 340,p. 256 - 263.

6
[ 2045-75-2 ]
[ 22744-12-3 ]
{4-[(4,4-dimethyl-pyrrolidin-2-ylidene)-acetyl]-phenyl}-acetic acid [ No CAS ]

References: [1]Journal fur Praktische Chemie - Chemiker-Zeitung,1998,vol. 340,p. 256 - 263.

7
[ 2412-58-0 ]
[ 22744-12-3 ]
{4-[2-3,4-Dihydro-2H-isoquinolin-(1Z)-ylidene-acetyl]-phenyl}-acetic acid [ No CAS ]

References: [1]Journal fur Praktische Chemie - Chemiker-Zeitung,1998,vol. 340,p. 256 - 263.

8
[ 1640-39-7 ]
[ 22744-12-3 ]
{4-[(3,3-dimethyl-1,3-dihydro-indol-2-ylidene)-acetyl]-phenyl}-acetic acid [ No CAS ]