19156-54-8|4,5,6,7-Tetrahydrobenzo[b]thiophene-3-carboxylic acid| Ambeed

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Quality Control of [ 19156-54-8 ] Purity: 97% SDS Specification

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Product Details of [ 19156-54-8 ]

CAS No. :	19156-54-8
Formula :	C₉H₁₀O₂S
M.W :	182.24
SMILES Code :	O=C(C1=CSC2=C1CCCC2)O
MDL No. :	MFCD00652575
InChI Key :	TUZZQEHPGHKGRJ-UHFFFAOYSA-N
Pubchem ID :	767738

Safety of [ 19156-54-8 ]

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

Computational Chemistry of [ 19156-54-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	5
Fraction Csp3	0.44
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	48.71
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.	1.75
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	2.36
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.33
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.	1.9
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	3.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.7
Solubility	0.364 mg/ml ; 0.002 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.	-3.38
Solubility	0.0766 mg/ml ; 0.00042 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	-2.15
Solubility	1.29 mg/ml ; 0.0071 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	Yes
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.	-5.74 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)	2.64

Application In Synthesis of [ 19156-54-8 ]

* 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 [ 19156-54-8 ]

[ 19156-54-8 ] Synthesis Path-Downstream 1~22

1
[ 14559-12-7 ]
[ 19156-54-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With water; potassium hydroxide; at 40℃;	General procedure: KOH (1.7 g, 30 mmol) was added to an emulsion of ester 3a-d (30 mmol) in H2O (20 ml). The mixture was heated with vigorous stirring until a clear solution was obtained (1 h) and then for further 30 min. The solution was cooled, washed with PhMe; the aqueous layer was separated and acidified with HCl to pH 4. The precipitate was filtered off and recrystallized from EtOH-DMF.

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2446 - 2455.
[2]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1748 - 1755.
Khim. Geterotsikl. Soedin.,2014,vol. 50,p. 1900 - 1907,8.

2
[ 4506-71-2 ]
[ 19156-54-8 ]

3
[ 19156-54-8 ]
[ 851634-59-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 2h;	<strong>[19156-54-8]4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid</strong> (1.0 g, 5.5 mmol) was dissolved in THF (11 mL) and borane·THF (0.94 mg, 0.95 M in THF solution , 11 mmol) at 0 C., and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution at 0 C., and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a crude product. The resulting crude product was purified by silica gel column chromatography (n-hexane ? n-hexane / ethyl acetate = 3/1) to give the title compound (0.97 g, colorless transparent oil, quantitative) was obtained
86%	With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 20℃; for 1.58333h;	A solution of <strong>[19156-54-8]4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid</strong> (400 mg, 2.2 mmol) in diethyl ether (10 mL) was added under nitrogen to lithium aluminium hydride (1M solution in tetrahydrofuran, 3 mL, 3 mmol) in diethyl ether (10 mL) dropwise over 5 minutes. The reaction was stirred at room temperature for 1.5 hours then quenched with saturated ammonium chloride solution. The products were extracted into diethyl ether (x3). The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give 4,5,6,7-tetrahydro-1-benzothien-3-ylmethanol (320 mg, 86%). 1H NMR (500 MHz, CDCl3) delta 6.99 (1H, s), 4.56 (2H, s), 2.76 (2H, t, J=5.5 Hz), 2.58 (2H, t, J=5.6 Hz), 1.86-1.79 (4H, m), 1.43 (1H, s).

References: [1]Patent: JP2016/222570,2016,A .Location in patent: Paragraph 0061.
[2]Patent: US2005/101586,2005,A1 .Location in patent: Page/Page column 13.

Yield	Reaction Conditions	Operation in experiment
		This was subjected to hydrolysis under basic conditions to give the title compound (85 g). melting point: 170-172 C.

5
[ 288251-78-5 ]
[ 19156-54-8 ]
[ 398137-02-5 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 18 N-[3-cyano-4-(4-hydroxypiperidin-1-yl)phenyl]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide By the reaction and treatment in the same manner as in Example 6 using <strong>[19156-54-8]4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid</strong> (1.2 g) and 5-amino-2-(4-hydroxypiperidin-1-yl)benzonitrile (1.3 g), the title compound (1.2 g) was obtained. melting point: 172-173 C. 1H-NMR (270 MHz, DMSO-d6)delta:1.55-1.63 (2H, m), 1.64-1.80 (4H, m), 1.86-1.90 (2H, m), 2.7-2.8 (4H, M), 2.87 (2H, t, J=9.2 Hz), 3.29-3.34 (2H, m), 3.65-3.68 (1H, m), 4.70 (1H, m), 6.98 (1H, d, J=8.6 Hz), 7.83 (1H, dd, J=2.6, 8.6 Hz), 7.92 (1H, s), 8.03 (1H, d, J=2.6 Hz), 10.10 (1H, S).

References: [1]Patent: US2003/203909,2003,A1 .

6
[ 19156-54-8 ]
[ 398137-25-2 ]
[ 398137-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	EXAMPLE 31 N-[3-cyano-4-(2,2-dimethyl-3-hydroxypropoxy)phenyl]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide By the reaction and treatment in the same manner as in Example 6 using <strong>[19156-54-8]4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid</strong> (0.78 g) and 5-amino-2-(2,2-dimethyl-3-hydroxypropoxy)benzonitrile monohydrochloride (1.0 g) and triethylamine (0.6 ml), the title compound (0.87 g) was obtained. melting point: 148-150 C. 1H-NMR (400 MHz, DMSO-d6)delta:0.94 (6H, s), 1.7-1.8 (4H, m), 2.7-2.8 (4H, m), 3.30 (2H, s), 3.89 (2H, s), 4.68 (1H, s), 7.22 (1H, d, J=8.8 Hz), 7.87 (1H, d, J=8.8 Hz), 7.92 (1H, s), 8.02 (1H, s), 10.12 (1H, brs).

References: [1]Patent: US2003/203909,2003,A1 .

7
[ 19156-54-8 ]
[ 315241-39-5 ]
[ 314251-04-2 ]

References: [1]Archiv der Pharmazie,2009,vol. 342,p. 420 - 427.

8
[ 19156-54-8 ]
C₉H₉ClOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;	General procedure: Oxalyl chloride (10 ml) and DMF (1 drop) were added dropwise with vigorous stirring to a solution of acid 5a,b (50 mmol) in CH2Cl2 (100 ml). The solution was stirred at room temperature until evolution of gases ceased (3 h). The solvent and excess of oxalyl chloride were removed under reduced pressure to afford pure acyl chlorides 6a,b

References: [1]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1748 - 1755.
Khim. Geterotsikl. Soedin.,2014,vol. 50,p. 1900 - 1907,8.

9
[ 19156-54-8 ]
N-(2,2-dimethoxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1748 - 1755.
Khim. Geterotsikl. Soedin.,2014,vol. 50,p. 1900 - 1907,8.

10
[ 19156-54-8 ]
6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-c]pyridin-1(2H)-one [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1748 - 1755.
Khim. Geterotsikl. Soedin.,2014,vol. 50,p. 1900 - 1907,8.

11
ethyl 2-diazo-4,5,6,7-tetrahydrobenzo[b]thiophene 3-carboxylate [ No CAS ]
[ 19156-54-8 ]

References: [1]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1748 - 1755.
Khim. Geterotsikl. Soedin.,2014,vol. 50,p. 1900 - 1907,8.

12
[ 578-66-5 ]
[ 19156-54-8 ]
C₂₄H₁₈N₂OS [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 1764 - 1767.

13
[ 578-66-5 ]
[ 19156-54-8 ]
C₁₈H₁₆N₂OS [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 1764 - 1767.

14
[ 19156-54-8 ]
2-(4,5,6,7-tetrahydrobenzo[b]thiophene-3-yl)acetonitrile [ No CAS ]