5928-51-8|3-(2-Thienyl)propionic Acid| Ambeed

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Quality Control of [ 5928-51-8 ] Purity: 97% SDS Specification

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Product Details of [ 5928-51-8 ]

CAS No. :	5928-51-8
Formula :	C₇H₈O₂S
M.W :	156.20
SMILES Code :	O=C(O)CCC1=CC=CS1
MDL No. :	MFCD00047093
InChI Key :	MJPVYTKZYZPIQA-UHFFFAOYSA-N
Pubchem ID :	703169

Safety of [ 5928-51-8 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	3261
Packing Group:	Ⅱ

Computational Chemistry of [ 5928-51-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	5
Fraction Csp3	0.29
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	40.67
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	65.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.41
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	1.83
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.77
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.	0.98
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	2.51
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.7

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.13
Solubility	1.15 mg/ml ; 0.00736 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.	-2.83
Solubility	0.233 mg/ml ; 0.00149 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	-1.83
Solubility	2.28 mg/ml ; 0.0146 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.	-5.95 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)	1.95

Application In Synthesis of [ 5928-51-8 ]

* 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 [ 5928-51-8 ]

[ 5928-51-8 ] Synthesis Path-Downstream 1~35

1
[ 5722-13-4 ]
[ 5928-51-8 ]

References: [1]Bulletin de la Societe Chimique de France,1948,p. 1083,1085.

2
[ 5928-51-8 ]
[ 802294-64-0 ]
[ 69997-09-7 ]

References: [1]Bulletin de la Societe Chimique de France,1954,p. 1349,1353.

3
[ 5928-51-8 ]
[ 59594-93-3 ]

References: [1]Bulletin de la Societe Chimique de France,1954,p. 1349,1353.

4
[ 5928-51-8 ]
[ 26359-22-8 ]

References: [1]Journal of the Chemical Society,1938,p. 2100,2103.

5
[ 5928-51-8 ]
[ 5834-04-8 ]

Yield	Reaction Conditions	Operation in experiment
90.9%	With thionyl chloride; In chloroform;	General procedure: The appropriate acetic acid (10 mmol) was brought to reflux with thionyl chloride (12 mmol) in chloroform (30 mL). The reaction was monitored by IR until absorption appeared between 1780 cm-1 and 1815 cm-1. The solvent was evaporated under reduced pressure.
	With thionyl chloride; for 1h;	To a solution of 2,5-diaminopyrimidine-4,6-diol hydrogen chloride (1.04 g, 5.8 mmol) in sodium hydroxide (17.8 mmol) solution (25 ml of H2O) was added 3-thiophen-2-ylpropionyl chloride (6.4 mmol). The latter was prepared by refluxing 3-thiophen-2-ylpropionic acid (6.4 mmol) in thionyl chloride (500 muL) for 1 hour whereupon the excess of thionyl chloride was removed by evaporation in vacuo. The reaction mixture was stirred at room temperature for 18 hours. The pH of the suspension was adjusted to approximately 6 and the solids were filtered off. The title compound (1.25 g) was characterized by its mass spectrum: MS m/z (%): 515 ([M+H]+, 100).
	With thionyl chloride; for 1h;Reflux;	Example 152 Synthesis of N-(2-amino-4,6-dihydroxypyrimidin-5-yl)-3-thiophen-2-yl-propionamide To a solution of 2,5-diaminopyrimidine-4,6-diol hydrogen chloride (1.04 g, 5.8 mmol) in sodium hydroxide (17.8 mmol) solution (25 ml of H2O) was added 3-thiophen-2-ylpropionyl chloride (6.4 mmol). The latter was prepared by refluxing 3-thiophen-2-ylpropionic acid (6.4 mmol) in thionyl chloride (500 muL) for 1 hour whereupon the excess of thionyl chloride was removed by evaporation in vacuo. The reaction mixture was stirred at room temperature for 18 hours. The pH of the suspension was adjusted to approximately 6 and the solids were filtered off. The title compound (1.25 g) was characterized by its mass spectrum: MS m/z (%): 515 ([M+H]+, 100).

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2306 - 2325.
[2]Bulletin de la Societe Chimique de France,1948,p. 1083,1085.
[3]Bulletin de la Societe Chimique de France,1954,p. 1349,1353.
[4]Journal of Organic Chemistry,1989,vol. 54,p. 299 - 308.
[5]European Journal of Organic Chemistry,2011,p. 3117 - 3121.
[6]Angewandte Chemie - International Edition,2011,vol. 50,p. 9423 - 9428.
[7]Patent: US2012/46278,2012,A1 .Location in patent: Page/Page column 62.
[8]MedChemComm,2014,vol. 5,p. 333 - 337.
[9]Patent: US2014/88088,2014,A1 .Location in patent: Paragraph 0902.
[10]Chemistry - A European Journal,2019,vol. 25,p. 2019 - 2024.

6
[ 26359-22-8 ]
[ 5928-51-8 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2779.
Journal of the American Chemical Society,1952,vol. 74,p. 1066.

7
[ 4475-24-5 ]
[ 5928-51-8 ]

References: [1]Bulletin de la Societe Chimique de France,1954,p. 1349,1353.

8
[ 1124-65-8 ]
[ 5928-51-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium on carbon; In methanol; under 760.051 Torr; for 11.5h;	EXAMPLE 1 3-Thiophen-2-yl-propionic Acid 3-(2-Thienyl)acrylic acid (5.00 g, 32.43 mmol) was combined with 20% Pd/C (0.20 g) and methanol (150 ML) and stirred under a hydrogen atmosphere (1 atm) for 5 hours.. Fresh catalyst (0.10 g) was added, and the reaction stirred another 6.5 hours under a hydrogen atmosphere (1 atm).. The catalyst was filtered and washed with EtOAc (3*40 ML).. The filtrates concentrated to give the title compound 1 as a brown oil that crystallized upon standing (5.27 g, 100%). 1H NMR (400 MHz, CDCl3) delta7.10 (d, 1H, J=5.13 Hz), 6.89 (m, 1H), 6.80 (d, 1H, J=2.20 Hz), 3.14 (t, 2H, J=7.57 Hz), 2.71 (t, 2H, J=7.57 Hz). MS (APCI) m/z 155 (M--1).
	palladium; In tetrahydrofuran;	A: 3-(2-Thienyl)propanoic acid Palladium on carbon (10%, 4.2 g) was added in one portion to a solution of 3-(2-thienyl)acrylic acid (15.59 g, 0.10 mol) in tetrahydrofuran (130 mL). The mixture was subjected to Parr hydrogenation conditions (45 psi, room temperature) for about 24 hours. Following filtration through Celite, the filtrate was concentrated down to dryness and gave a brown-colored solid which was recrystallized from water. There was isolated 9.32 g (60%) of the title compound as a mixture of white and tan colored needles, m.p. 58-60 C. (m.p. lit. 62-62.5 C.); 1 H NMR (CD3 SOCD3) 6 12.2 (br s, 1H), 7.23-7.21 (m, 1H), 6.89-6.86 (m, 1H), 6.82-6.81 (m, 1H), 2.99 (t, J=7.4 Hz, 2H), 2.53 (t, J=7.4 Hz, 2H); 13C NMR (CD3 SOCD3) ppm 173.42, 143.39, 126.90, 124.70, 123.72, 35.61, 24.70; IR (KBr, cm-1) 3102-3036, 2922, 2644, 1706, 1440, 1408, 1310, 1232, 1220, 938, 848, 828, 714, 692; MS m/z (MH+) 157. Anal. Calcd for C7 H8 O2 S: C, 53.83; H, 5.16. Found: C, 53.90; H, 5.16.
	palladium; In ethanol;	PREPARATION 11 3-(2-Thienyl)propionic Acid To a solution of 3-(2-thienyl)acrylic acid (7 g) in ethanol was added 5% palladium on carbon and the mixture was hydrogenated at 50 psi in a Parr apparatus. The catalyst was filtered off and the solvent was removed by evaporation to yield the title compound (5.5 g) as an oil. Electrospray MS m/z 155 [M-H]+.

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2329 - 2332.
[2]Patent: US6710190,2004,B1 .Location in patent: Page column 17.
[3]Journal of the Chemical Society. Perkin transactions II,1993,p. 1941 - 1946.
[4]Journal of the Chemical Society,1938,p. 2100,2103.
[5]Patent: US5380713,1995,A .
[6]Patent: US6218538,2001,B1 .

9
[ 15690-25-2 ]
[ 5928-51-8 ]

References: [1]European Journal of Medicinal Chemistry,1989,vol. 24,p. 65 - 72.
[2]Chemical Papers,2013,vol. 67,p. 59 - 65,7.

10
[ 67-56-1 ]
[ 5928-51-8 ]
[ 16862-05-8 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 5221 - 5226.

11
[ 5928-51-8 ]
[ 64-17-5 ]
[ 64107-46-6 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; for 66h;	2-Thiophenepropionic acid (10 g, 64 mmol) was dissolved in 50 mL ethanol. Concentrated sulfuric acid (1 mL) was added and the solution was stirred for 66 hours. The solvents were then removed in vacuo and the residue dissolved in 100 mL ethyl ether. The organics were washed twice with 50 mL saturated NaHCO3 and once with 50 mL brine then dried with Na2SO4. Concentration of the organics in vacuo yielded ethyl-2- thiophenepropionate (10.85 g, 58.9 mmol) as an orange oil.
	With sulfuric acid; for 66h;	A. 2-Thiophenepropionic acid (10 g, 64 mmol) was dissolved in 50 mL ethanol. Concentrated sulfuric acid (1 mL) was added and the solution was stirred for 66 hours. The solvents were then removed in vacuo and the residue dissolved in 100 mL ethyl ether. The organics were washed twice with 50 mL saturated NaHCO3 and once with 50 mL brine then dried with Na2SO4. Concentration of the organics in vacuo yielded ethyl-2-thiophenepropionate (10.85 g, 58.9 mmol) as an orange oil.
	With thionyl chloride;	8. Preparation of ethyl 3-(2-thienyl)propanoate Scheme 15 Ethyl 3-(2-thienyl)propanoate was synthesized with thionyl chloride and methanol from 3-(2- thienyl)propanoic acid. The reaction was carried out according to available literature36, 37, 38.

References: [1]European Journal of Medicinal Chemistry,1989,vol. 24,p. 65 - 72.
[2]Patent: WO2003/87090,2003,A2 .Location in patent: Page/Page column 100.
[3]Patent: US2004/192720,2004,A1 .Location in patent: Page 42.
[4]Patent: WO2014/106763,2014,A1 .Location in patent: Page/Page column 22.
[5]Journal of Natural Products,2015,vol. 78,p. 1859 - 1867.

12
[ 5928-51-8 ]
[ 23583-21-3 ]
[ 96103-41-2 ]

References: [1]Synthesis,1984,p. 1071 - 1073.

13
[ 5928-51-8 ]
[ 87-25-2 ]
[ 96103-34-3 ]

References: [1]Synthesis,1984,p. 1071 - 1073.

14
[ 5928-51-8 ]
[ 88388-04-9 ]

References: [1]Chemistry Letters,1983,p. 1475 - 1476.

15
[ 98-03-3 ]
[ 2033-24-1 ]
[ 5928-51-8 ]

References: [1]Synthetic Communications,1995,vol. 25,p. 3067 - 3074.

16
[ 5928-51-8 ]
[ 96021-69-1 ]
[ 138296-00-1 ]

References: [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 489 - 508.

17
[ 5928-51-8 ]
[ 64-19-7 ]
thorium oxide [ No CAS ]
[ 59594-93-3 ]

References: [1]Bulletin de la Societe Chimique de France,1954,p. 1349,1353.

19
[ 1003-09-4 ]
[ 3984-22-3 ]
[ 5928-51-8 ]

References: [1]Tetrahedron,2004,vol. 60,p. 11533 - 11540.

20
[ 5928-51-8 ]
[ 130062-64-5 ]
[ 908856-10-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4420 - 4423.

21
[ 5928-51-8 ]
[ 79-22-1 ]
[ 16862-05-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dmap; triethylamine; In dichloromethane; at 0℃; for 0.5h;	EXAMPLE 2 3-Thiephen-2-yl-propionic Acid Methyl Ester Compound 1 (5.00 g, 32.01 mmol) was dissolved in anhydrous CH2Cl2 (100 ML) and cooled in an ice bath while stirring under N2.. triethyl amine (4.95 ML, 35.53 mmol) was added, and the reaction stirred for 5 minutes.. methyl chloroformate (2.48 ML, 32.05mmol) was added, the reaction stirred for 5 minutes, and DMAP (0.38 g, 3.11 mmol) added.. The reaction was stirred at 0 C. for 30 minutes, and then diluted with CH2Cl2 (200 ML).. The organics were washed with saturated NaHCO3 (100 ML), 0.1 M HCl (100 ML), brine (100 ML), and dried over MgSO4.. The crude material was chromatographed on SiO2 eluding with 7% EtOAc/hexanes to give the title compound 2 (3.976 g 73%) as a colorless oil). 1H NMR (400 MHz, CDCl3) delta7.10 (dd, 1H, J=4.64, 0.98 Hz), 6.88 (t, 1H, J=4.27 Hz), 6.78 (dd, 1H, J=2.20, 0.98 Hz), 3.66 (s, 3H), 3.13 (t, 2H, J=7.57 Hz), 2.66 (t, 2H, J=7.57 Hz). MS (APCI) m/z 171 (M++1).

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2329 - 2332.
[2]Patent: US6710190,2004,B1 .Location in patent: Page column 18.

22
[ 851484-80-5 ]
[ 5928-51-8 ]
2-Methyl-propane-2-sulfinic acid ((S)-3-methyl-1-{2-[4-(3-thiophen-2-yl-propionyl)-piperazin-1-yl]-5-trifluoromethyl-phenyl}-butyl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4674 - 4678.

23
[2-(4-aminomethyl-phenyl)-oxazol-4-yl]-piperidin-1-yl-methanone; hydrochloride [ No CAS ]
[ 5928-51-8 ]
<i>N</i>-{4-[4-(piperidine-1-carbonyl)-oxazol-2-yl]-benzyl}-3-thiophen-2-yl-propionamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4554 - 4558.

24
[ 5928-51-8 ]
[ 906540-99-6 ]
[ 906541-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane; at 20℃;	Preparation 7.3 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N'-[[3-(2-thienyl)propanoyl]oxy]-1H-pyrazole-3-carboximidamide 0.168 g of HOBT and then 0.19 ml of N,N'-diisopropylcarbodiimide are added to a mixture of 0.4 g of the compound from Preparation 6.1 and 0.158 g of <strong>[5928-51-8]3-(2-thienyl)propanoic acid</strong> in 10 ml of DCM and the mixture is left stirring at AT overnight. The reaction mixture is concentrated under vacuum, the residue is extracted with ether, the organic phase is washed with a 10% NaHCO3 solution, with water and with a 0.5M KHSO4 solution and dried over MgSO4, and the solvent is evaporated under vacuum. 0.53 g of the expected compound is obtained.

References: [1]Patent: US2008/39510,2008,A1 .Location in patent: Page/Page column 24.

25
[ 5928-51-8 ]
3-aminomethyl-4-(thiophen-2-yl)butyric acid [ No CAS ]