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CAS No. : | 40133-06-0 | MDL No. : | MFCD01860021 |
Formula : | C8H8O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XSFUFVBXPLWNBK-UHFFFAOYSA-N |
M.W : | 168.21 | Pubchem ID : | 770980 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
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th. Decarboxylierung m. Cu; |
Yield | Reaction Conditions | Operation in experiment |
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4a, methanol.KOH; |
Yield | Reaction Conditions | Operation in experiment |
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With oxalyl dichloride In dichloromethane at 20℃; for 2h; | 137.A Step A:; Oxalyl chloride (0.11 mL, 1.31 mmol) was added to a suspension of 5,6-dihydro-4H-cyclopent[b]thiophene-2-carboxylic acid (200 mg, 1.19 mmol) in methylene chloride (2 mL) at room temperature and the mixture was stirred under nitrogen for 2 h. 3-Hydroxyanthranilic acid hydrobromide (278 mg, 1.19 mmol) was added, followed by triethylamine (0.83 mL, 5.95 mmol) and methylene chloride (3 mL). The resulting mixture was stirred under nitrogen overnight, and then quenched with 1 N HCl. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the crude product (340 mg, 94%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 11.75 (br s, 1H), 10.28 (br s, 1H), 7.73 (dd, J=8.0, 1.5 Hz, 1H), 7.57 (s, 1H), 7.33 (dd, J=8.0, 1.5 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H), 2.98 (t, J=7.5 Hz, 2H), 2.81 (t, J=7.5 Hz, 2H), 2.53-2.47 (m, 2H); MS (ESI+) m/z 304 (M+H). | |
With thionyl chloride | S.3.1 Synthesis of N'-t-butyl-N'-3,5-dimethylbenzoyl-N-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carbohydrazide (Compound No. 34 as described hereinafter) (1) 1.0 g of 5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylic acid was reacted with 4 ml of thionyl chloride for 3.5 hours under reflux. Then, excess thionyl chloride was distilled off under reduced pressure to obtain 5,6-dihydro-4H-cyclopenta[b]thiophene-2-carbonyl chloride. |
Yield | Reaction Conditions | Operation in experiment |
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80% | With tetrabutyl-ammonium chloride; caesium carbonate In N,N-dimethyl-formamide at 170℃; for 0.133333h; Microwave irradiation; | 45 Example 45: Synthesis of a compound 1074 via decarboxylative biaryl cross coupling reactions The decarboxylative cross coupling reactions are used to prepare a variety of inhibitors; the details of the synthetic methodology can be found in the literature reference: J. Am. Chem. Soc. 2006, 128, 11350-11351. An example is shown below:In a vial suitable for microwave reactions is added 5,6-dihydro-4H- cyclopenta[b]thiophene-2-carboxylic acid (73 mg, 0.44 mmol), 4-iodoquinoline 1i (100 mg, 0.24 mmol), tetrabutylammonium chloride hydrate (67 mg, 0.24 mmol), cesium carbonate (118 mg, 0.36 mmol), and the catalyst Pd[(PtBu)3]2 (12.4 mg, 0.02 mmol) in DMF (3 ml_). The vial is then capped and submitted directly to the microwave conditions: 1700C for 8 min. After cooling, the reaction is diluted with EtOAc (100 ml_) and the mixture is washed with brine (3x), water (1x), before being dried (MgSO4), filtered and concentrated. The residue is purified by CombiFlash Companion (hexanes/EtOAc) to afford the methyl ester of the desired product (79 mg, 80% yield) as a foamy solid. The final compound 1074 is obtained after a saponification step followed by HPLC purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With lithium hydroxide In tetrahydrofuran; ethanol; water at 50℃; for 3h; | 1.1.4 Synthesis of compound 1.4 To a solution of methyl 4H,5H,6H- cyclopenta[b]thiophene-2-carboxylate (1 g, 5.49 mmol, 1.00 equiv) in a THF/ EtOH / water (10/10/10 mL) mixture was added LiOH (660 mg) at room temperature. The resulting solution was stirred for 3 h at 50 °C in an oil bath and then diluted with 20 mL of water. The pH value of the solution was adjusted to 5 with 2 M aqueous hydrochloric acid. The precipitate was collected by filtration and dried in an oven under reduced pressure to give the desired 4H,5H,6H- cyclopenta[b]thiophene-2-carboxylic acid (0.84 g, 91%) as an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C 3: dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C 3: dichloromethane 4: diphenylether / 0.5 h / 220 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C 3: dichloromethane 4: diphenylether / 0.5 h / 220 °C / Inert atmosphere 5: trichlorophosphate / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C 3: dichloromethane 4: diphenylether / 0.5 h / 220 °C / Inert atmosphere 5: trichlorophosphate / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 6: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / toluene / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C 3.1: dichloromethane 4.1: diphenylether / 0.5 h / 220 °C / Inert atmosphere 5.1: trichlorophosphate / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 6.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 6.2: 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C 3: dichloromethane 4: diphenylether / 0.5 h / 220 °C / Inert atmosphere 5: trichlorophosphate / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 6: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / toluene / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: diphenylphosphoranyl azide; triethylamine / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C 3.1: dichloromethane 4.1: diphenylether / 0.5 h / 220 °C / Inert atmosphere 5.1: trichlorophosphate / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 6.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 6.2: 3 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With diphenylphosphoranyl azide; triethylamine Inert atmosphere; Reflux; | 1.1.5 Synthesis of compound 1.5 To a solution of 4H,5H,6H-cyclopenta[b]thiophene-2- carboxylic acid (1.68 g, 9.99 mmol, 1.00 equiv) in tert-butanol (25 mL) was added DPPA (4.95 g, 17.99 mmol, 1.80 equiv) and triethylamine (3.03 g, 29.94 mmol, 3.00 equiv) at room temperature under nitrogen. The resulting solution was heated to reflux overnight in an oil bath and concentrated in vacuo. The residue was diluted with 100 mL of ethyl acetate and washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 10) to provide 1.6 g (67%)) of tert-butyl N-[4H,5H,6H-cyclopenta[b]thiophen-2-yl]carbamate as a white solid. MS (ES): m/z 240 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate / toluene / 2 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / pyridine / 1 h / 0 - 20 °C 3: lithium hydroxide / tetrahydrofuran; ethanol; water / 3 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: triethylamine / pyridine / 1 h / 0 - 20 °C 2: lithium hydroxide / tetrahydrofuran; ethanol; water / 3 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 25 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -75 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 25 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -75 - 25 °C 3: trifluoroacetic acid / acetonitrile / 6 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 25 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -75 - 25 °C 3: trifluoroacetic acid / acetonitrile / 6 h / 25 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 25 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -75 - 25 °C 3: trifluoroacetic acid / acetonitrile / 6 h / 25 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Reflux 5: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 25 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -75 - 25 °C 3: trifluoroacetic acid / acetonitrile / 6 h / 25 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Reflux 5: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 0.15 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.2% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; | 38.1 Step 1 To a mixture of 28a (3.0 g, 20.0 mmol), compound Ν,Ο- dimethyldroxylamine hydrochloride (2.0 g, 20.6 mmol) and DIPEA (20.6 mmoL) inDMF (15 mL) was added HATU (7.6 g, 20.0 mmol). The resulting mixture was stirred at 25 °C. LCMS judged the starting material was consumed up. The crude product was purified using Si02 chromatography (petroleum ether: ethyl acetate = 8: 1 to 5: 1) to provide compound 28b (3.0 g, 80.2% yield) |
80.2% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; | 38.1 Step 1 To a mixture of 28a (3.0 g, 20.0 mmol), compound Ν,Ο- dimethyldroxylamine hydrochloride (2.0 g, 20.6 mmol) and DIPEA (20.6 mmoL) in DMF (15 mL) was added HATU (7.6 g, 20.0 mmol). The resulting mixture was allowed to stir at 25 °C. LCMS judged the starting material was consumed up. The crude product was purified using Flash column chromatography on silica gel (petroleum ether: ethyl acetate = 8: 1 to 5: 1) to provide compound 28b (3.0 g, 80.2% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 2h; | 21 Example 21. Preparation of Compound N-[2-oxo-2-[(4-phenylthiazol-2-yl)amino]ethyl]-5,6-dihydro- 4H-cyclopenta[b]thiophene-2-carboxamide (compound 79) To a solution of 5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylic acid (30.0 mg, 178.35 pmol), HATU (67.81 mg, 178.35 pmol) and DIPEA (83.82 mg, 648.53 pmol, 1 12.96 pL) in DCM (0.5 mL) was added 2-amino-N-(4-phenylthiazol-2-yl)acetamide (56.31 mg, 162.13 pmol, TFA salt). The mixture was stirred at 20 °C for 2 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was triturated with MeOH (1 0.0 mL), the solid was collected by filtration and dried in vacuum to give compound 79 as a white solid 1 H NMR (400MHz, DMSO-de) d = 12.41 (s, 1 H), 8.79-8.76 (m, 1 H), 7.91 (d, J= 7.2 Hz, 2H), 7.64-7.58 (m, 2H), 7.46-7.42 (m, 2H), 7.37-7.30 (m, 1 H), 4.15 (d, J= 6.0 Hz, 2H), 2.90-2.87 (m, 2H), 2.78-2.69 (m, 2H), 2.41 -2.37 (m, 2H) ppm. LCMS (ESI) m/z: [M+H]+ = 384.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -25 °C / Inert atmosphere 1.2: -25 - 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylic acid With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -25℃; for 1h; Inert atmosphere; Stage #2: Diethyl disulfide In tetrahydrofuran; hexane at -25 - 20℃; | 3-(Ethylsulfanyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylic acid 3-(Ethylsulfanyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylic acid Under an atmosphere of argon, 2,2,6,6-tetramethylpiperidine (1.847 g, 13.0 mmol) was dissolved in 20 ml of dry THF and cooled to -25° C. n-Butyllithium (2.5 M in hexane, 13.0 mmol) was slowly added dropwise and the mixture was stirred for 30 min. 5,6-Dihydro-4H-cyclopenta[b]thiophene-2-carboxylic acid (1.00 g, 5.94 mmol) dissolved in 5 ml of THF was added dropwise to the reaction solution. After 30 min of stirring at -25° C., diethyl disulfide (1.816 g, 14.8 mmol) was added dropwise and the mixture was stirred for a further 30 min. The mixture was slowly warmed to room temperature and then concentrated on a rotary evaporator. The residue was taken up in cyclohexane and the resulting precipitate was isolated by filtration. The organic phase was washed twice with 1N hydrochloric acid solution, dried over sodium sulfate and freed of the solvent. The crude product was used in the subsequent reaction without further purification. MH+:229; 1H-NMR (400 MHz, CDCl3) δ ppm: 3.06-3.01 (q, 2H), 2.90-2.68 (m, 6H), 1.17-1.14 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -25 °C / Inert atmosphere 1.2: -25 - 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h / 20 °C 3.1: dihydrogen peroxide; formic acid / dichloromethane; water / 12 h / 20 °C 4.1: dipotassium peroxodisulfate; Selectfluor / water; acetonitrile / 3 h / 80 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -25 °C / Inert atmosphere 1.2: -25 - 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h / 20 °C 3.1: dihydrogen peroxide; formic acid / dichloromethane; water / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 23 °C 2: hydrogenchloride / methanol / 4 h / 23 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 23 °C 2.1: hydrogenchloride / methanol / 4 h / 23 °C / Cooling with ice 3.1: triethylamine / dichloromethane / 0.08 h / Cooling with ice 3.2: 12 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 23 °C 2.1: hydrogenchloride / methanol / 4 h / 23 °C / Cooling with ice 3.1: triethylamine / dichloromethane / 0.08 h / Cooling with ice 3.2: 12 h / 23 °C 4.1: 3,3-dimethyldioxirane / dichloromethane / 18 h / 23 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 23℃; for 16h; |
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