5467-53-8|4-(4-Ethylphenyl)butanoic acid| Ambeed

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Quality Control of [ 5467-53-8 ] Purity: 95% SDS Specification

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Product Details of [ 5467-53-8 ]

CAS No. :	5467-53-8
Formula :	C₁₂H₁₆O₂
M.W :	192.25
SMILES Code :	CCC1=CC=C(CCCC(O)=O)C=C1
MDL No. :	MFCD01462080
InChI Key :	IDXWSFCOUZYCMF-UHFFFAOYSA-N
Pubchem ID :	231606

Safety of [ 5467-53-8 ]

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

Computational Chemistry of [ 5467-53-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	5
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	57.37
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.21
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	3.22
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.66
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.	2.86
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	3.11
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.81

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.05
Solubility	0.172 mg/ml ; 0.000896 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.	-3.68
Solubility	0.0405 mg/ml ; 0.000211 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	-3.78
Solubility	0.0319 mg/ml ; 0.000166 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.	-5.19 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)	1.17

Application In Synthesis of [ 5467-53-8 ]

* 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 [ 5467-53-8 ]

[ 5467-53-8 ] Synthesis Path-Downstream 1~34

1
[ 96-48-0 ]
[ 100-41-4 ]
[ 5467-53-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1955,vol. 596,p. 1,220.

2
[ 5467-53-8 ]
[ 412321-18-7 ]

References: [1]Journal of the Chemical Society,1939,p. 944,948.

3
[ 5467-53-8 ]
[ 22531-06-2 ]

Yield	Reaction Conditions	Operation in experiment
84%		To a solution of carboxylic acid 41 (1.91 g, 9.93 mmol) and anhydrous DMF (7 drops) in anhydrous DCM (30 mL) cooled to 0 C was added oxalyl chloride (1.68 mL, 19.9 mmol) dropwise. The contents were stirred at 0 C for 1 hour, then at room temperature for 1.5 hours. The mixture was cooled to 0 C, and aluminium chloride (2.65 g, 19.9 mmol) was added. The reaction was returned to room temperature, stirred for 18 hours, and quenched at 0 C with 1N aqueous HC1 (7 mL). The reaction mixture was diluted with EtOAc (200 mL) and washed with brine (100 mL). The organic phase was dried over anhydrous Na2S04 and concentrated under reduced pressure. Purification by flash column chromatography (hexanes to 90: 10 hexanes/EtOAc) afforded 42 as a pale yellow oil (1.45 g, 84% yield). Rf = 0.40 (hexanes/EtOAc 90: 10 v/v). 1H NMR (400 MHz, CDCl3) delta 7.88 (s, 1H), 7.32 (d , J= 9.1 Hz, 1H), 7.17 (d, J= 7.8 Hz, 1H), 2.93 (t, J= 6.1 Hz, 2H), 2.71-2.62 (m, 4H), 2.12 (app quint, J= 6.4 Hz, 2H), 1.24 (t, J= 7.6 Hz, 3H). 13C NMR (101 MHz, CDCl3) delta 198.8, 142.9, 142.0, 133.4, 132.6, 128.9, 126.3, 39.4, 29.5, 28.6, 23.6, 15.7. MS (ESI+) calculated for [Ci2Hi50]+ [M+H]+, 175.1; found 175.1.
	With PPA;	STAGE C 7-ETHYLTETRALONE STR53 25 g of polyphosphoric acid are poured into a 100-cm3 ground-necked round-bottomed flask. 2.5 g of 4-(4-ethylphenyl)butyric acid are added. The reaction mixture is stirred for 6 h at a temperature of 45 C. It is poured into ice. The resulting mixture is extracted with 3 volumes of ether. The organic phases are washed 3 times with 10% potassium carbonate solution, dried over magnesium sulfate and then evaporated to dryness. The oil obtained is purified by column chromatography. Infrared spectroscopic analysis: 3010 cm-1: nu aromatic CH 2980-2860 cm-1: nu alkyl CH 1680 cm-1: nu ketone CO 1605 cm-1: nu aromatic C=C

References: [1]ChemMedChem,2018,vol. 13,p. 1092 - 1097.
[2]Patent: WO2019/178480,2019,A1 .Location in patent: Page/Page column 111; 112.
[3]Chemische Berichte,1923,vol. 56,p. 630.
[4]Chemical and pharmaceutical bulletin,1968,vol. 16,p. 2456 - 2462.
[5]Journal of the Indian Chemical Society,1992,vol. 69,p. 26 - 28.
[6]Journal of the American Chemical Society,1940,vol. 62,p. 2219,2221.
Journal of the American Chemical Society,1940,vol. 62,p. 2550.
[7]Patent: US5731352,1998,A .
[8]Annales de Chimie (Cachan, France),1938,vol. <11> 9,p. 5,82.
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1936,vol. 202,p. 1679.

4
[ 5467-53-8 ]
4-(4-ethyl-cyclohexyl)-butyric acid [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1955,vol. 596,p. 1,220.

5
[ 5467-53-8 ]
[ 855215-98-4 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 2219,2221.
Journal of the American Chemical Society,1940,vol. 62,p. 2550.
[2]Annales de Chimie (Cachan, France),1938,vol. <11> 9,p. 5,82.
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1936,vol. 202,p. 1679.

6
[ 49594-75-4 ]
[ 5467-53-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With zinc amalgam; In water; for 17h;Reflux;	To a solution of mercuric chloride (666 mg, 2.45 mmol) in water (7 mL) and concentrated HC1 (20 mL) was slowly added zinc (6.66 g, 102 mmol). After bubbling subsided, additional portions of mercuric chloride (666 mg, 2.45 mmol) and zinc (6.66 g, 102 mmol) were added. The contents were stirred for 30 minutes at roomtemperature. The liquid was decanted, and the solid amalgam was washed twice with water. A solution of 4-(4-ethylphenyl)-4-oxobutyric acid (3.00 g, 14.5 mmol) in toluene (7.5 mL), water (15 mL), and concentrated HC1 (15 mL) was then added to the mercury-zinc amalgam. The mixture was heated at reflux for 17 hours, then filtered. The filtrate was diluted with EtOAc (200 mL) and washed with brine (100 mL). The organic phase was dried over anhydrous Na SCL and concentrated under reduced pressure. Purification by flash column chromatography (DCM to 25:75 DCM/EtOAc) afforded 41 as a white solid (2.04 g, 73% yield). Rf= 0.27 (DCM/EtOAc 50:50 v/v).1H NMR (400 MHz, DMSO-r6) delta 12.03 (br s, 1H), 7.11 (d, J= 8.2 Hz, 2H), 7.08 (d, J = 8.2 Hz, 2H), 2.60-2.48 (m, 4H), 2.20 (t, J= 7.4 Hz, 2H), 1.77 (app quint, J= 7.5 Hz, 2H), 1.16 (t, J= 7.6 Hz, 3H).13C NMR (101 MHz, DMSO-d6) delta 174.3, 141.1, 138.7, 128.2, 127.7, 34.0, 33.1, 27.8, 26.4, 15.7. MS (ESI+) calculated for [Ci2Hi50]+[M-OH]+, 175.1; found 175.1.
	With nitrogen;	B. 4-(4-Ethylphenyl)-butanoic acid To a 500 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 41.2 grams (200 mmol) 3-(4-ethylbenzoyl)-propionic acid, activated zinc prepared from 82.4 grams (400 mmol) mossy zinc and 8.2 grams mercuric chloride in 125 mL water and 8 mL concentrated hydrochloric acid, 77 mL water, 177 mL concentrated hydrochloric acid, and 100 mL toluene.
	With hydrogenchloride; triethylsilane; In trifluoroacetic acid;	STAGE B 4-(4-ETHYLPHENYL)BUTYRIC ACID STR52 In a 100-cm3 flask, 2.5 g of 4-oxo-4-(4-ethylphenyl)butyric acid are dissolved with magnetic stirring in 19 cm3 of trifluoroacetic acid. 3.2 g of triethylsilane are added dropwise. The reaction mixture is stirred for 86 hours at room temperature. It is poured into ice. It is extracted with 3 volumes of ether. The organic phases are washed 3 times with 10% potassium carbonate solution. The aqueous phases are combined and then acidified by adding concentrated hydrochloric acid until the pH is 3-4. The precipitate obtained is drained and then recrystallized. Infrared spectroscopic analysis: 3280-2780 cm-1: nu acid OH 2940-2850 cm-1: nu alkyl CH 1680 cm-1: nu acid CO 1510 cm-1: nu aromatic C=C

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1991,vol. 57,p. 227 - 233.
[2]ChemMedChem,2018,vol. 13,p. 1092 - 1097.
[3]Patent: WO2019/178480,2019,A1 .Location in patent: Page/Page column 111; 112.
[4]Journal of Organic Chemistry,1950,vol. 15,p. 950,954.
[5]Justus Liebigs Annalen der Chemie,1955,vol. 596,p. 1,222.
[6]Chemische Berichte,1923,vol. 56,p. 630.
[7]European Journal of Medicinal Chemistry,1996,vol. 31,p. 683 - 692.
[8]Patent: US5618811,1997,A .
[9]Patent: US5731352,1998,A .

7
[ 855221-60-2 ]
[ 5467-53-8 ]

References: [1]Annales de Chimie (Cachan, France),1938,vol. <11> 9,p. 5,82.
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1936,vol. 202,p. 1679.

8
[ 5467-53-8 ]
[ 183129-81-9 ]

References: [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 1190 - 1201.
[2]European Journal of Medicinal Chemistry,1996,vol. 31,p. 683 - 692.

11
[ 7647-01-0 ]
[ 49594-75-4 ]
amalgamated zinc [ No CAS ]
[ 5467-53-8 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 630.

12
[ 7664-93-9 ]
[ 5467-53-8 ]
[ 22531-06-2 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 630.

13
[ 100-41-4 ]
oxygen [ No CAS ]
[ 5467-53-8 ]