19418-11-2|Tetrahydrothiophene-2-carboxylic acid| Ambeed

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Quality Control of [ 19418-11-2 ] Purity: 97% SDS Specification

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Product Details of [ 19418-11-2 ]

CAS No. :	19418-11-2
Formula :	C₅H₈O₂S
M.W :	132.18
SMILES Code :	O=C(C1CCCS1)O
MDL No. :	MFCD11520782
InChI Key :	MZOYMQRKTJRHGJ-UHFFFAOYSA-N
Pubchem ID :	443066

Safety of [ 19418-11-2 ]

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

Computational Chemistry of [ 19418-11-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	0
Fraction Csp3	0.8
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	33.4
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.07
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	0.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.97
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.	0.5
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	1.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.93

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.22
Solubility	8.02 mg/ml ; 0.0606 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.89
Solubility	1.69 mg/ml ; 0.0128 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.21
Solubility	81.9 mg/ml ; 0.619 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.	-6.4 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)	2.83

Application In Synthesis of [ 19418-11-2 ]

* 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 [ 19418-11-2 ]

[ 19418-11-2 ] Synthesis Path-Downstream 1~35

1
[ 527-72-0 ]
[ 19418-11-2 ]

References: [1]Chemische Berichte,1887,vol. 20,p. 518.

2
[ 19418-11-2 ]
[ 63521-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;	EXAMPLE 27 1-[N-(2-Tetrahydrothienyl)carbamoyl]-5-fluorouracil Thionyl chloride (16.5 g.) was added to <strong>[19418-11-2]2-tetrahydrothiophenecarboxylic acid</strong> (12.2 g.) at ambient temperature and heated for 2 hours at 80 C. The reaction mixture was evaporated to dryness under reduced pressure and the residual oil was fractionated by distillation in vacuo to give <strong>[19418-11-2]2-tetrahydrothiophenecarboxylic acid</strong> chloride (9.79 g.), (b.p. 46 C./1 mmHg).
	With thionyl chloride; In dichloromethane; at 20℃; for 3h;	Step 1 Methoxymethyltetrahydrothiophene-2-carboxylamide 32.0 ml (0.44 mol; 1.27 eq) of thionyl chloride were added dropwise, at ambient temperature, over the course of 15 minutes, to a solution of 46.0 g (0.35 mol; 1.0 eq) of <strong>[19418-11-2]tetrahydrothiophene-2-carboxylic acid</strong> (commercial) in 200 ml of dichloromethane. The reaction medium was stirred at ambient temperature for 3 hours until no more gas was given off. The dichloromethane and the excess thionyl chloride were evaporated off under vacuum and the residue was co-evaporated three times with 100 ml of toluene. The acid chloride obtained was solubilized in 200 ml of dichloromethane, and 37.34 g (0.38 mol; 1.1 eq) of N,O-dimethylhydroxylamine hydrochloride were added. The reaction medium was cooled to -10 C. and a mixture of 116 ml (0.84 mol; 2.4 eq) of triethylamine in 100 ml of dichloromethane was added dropwise over the course of one hour (while maintaining the temperature below 5 C.). After the addition, the reaction medium was stirred at ambient temperature for one hour and was then washed with 250 ml of a 1 M aqueous hydrochloric acid solution. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with 200 ml of a 1 M aqueous sodium hydrogen phosphate solution, dried over anhydrous magnesium sulfate, filtered and evaporated. 51.0 g of methoxymethyltetrahydrothiophene-2-carboxylamide were obtained in the form of an orange oil. Yield=84%.

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 9190 - 9196.
[2]Synthesis,1987,p. 452 - 455.
[3]Journal of the Chemical Society, Dalton Transactions,1992,p. 2873 - 2876.
[4]Patent: US4349552,1982,A .
[5]Patent: US2014/296254,2014,A1 .Location in patent: Paragraph 0113.

3
[ 112212-94-9 ]
[ 19418-11-2 ]

References: [1]Synthesis,1987,p. 452 - 455.

4
[ 527-72-0 ]
[ 19418-11-2 ]
(+)-3-Hydroxytetrahydrothiophene-2-carboxylic acid [ No CAS ]

References: [1]Agricultural and Biological Chemistry,1982,vol. 46,p. 1429 - 1438.
[2]Agricultural and Biological Chemistry,1982,vol. 46,p. 1429 - 1438.

Yield	Reaction Conditions	Operation in experiment
		To a stirred suspension of potassium bufoxide in THF is added TOSMIC (tosylmethylisocyanide, 3.9 g) at 7-10 C. This is followed by 1.92 g thiolactam in 20 ml THF. After 5 minutes, 2 ml acetic acid is dripped in. The solution is concentrated, taken up in water, and extracted with methylene chloride. The combined organic residue is dried and concentrated, then 40 ml 2N HCl added and refluxed 12 hours. The solution is made basic and extracted with ether. The aqueous layer is taken to pH 1, extracted again with ether and these organics combined, dried, and concentrated to give the product tetrahydrothienylcarboxylic acid, mp 95-98 C.

7
(+-)-5-chloro-2-mercapto-valeric acid methyl ester [ No CAS ]
[ 19418-11-2 ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1958,p. 852,854;engl.Ausg.S.828,830.

8
(+-)-5-chloro-2-mercapto-valeric acid [ No CAS ]
[ 19418-11-2 ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1958,p. 852,854;engl.Ausg.S.828,830.

9
sodium-salt of/the/ (+-)-2,5-dichloro-valeric acid [ No CAS ]
[ 19418-11-2 ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1958,p. 852,854;engl.Ausg.S.828,830.

10
[ 98486-29-4 ]
aqueous NaOH-solution [ No CAS ]
[ 19418-11-2 ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1958,p. 852,854;engl.Ausg.S.828,830.

11
[ 19418-11-2 ]
[ 219532-31-7 ]