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CAS No. : | 882303-63-1 | MDL No. : | |
Formula : | C16H8N2O2S3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MYFMYUMBJOVSJX-UHFFFAOYSA-N |
M.W : | 356.44 | Pubchem ID : | 86234384 |
Synonyms : |
|
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 19 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 94.82 |
TPSA : | 144.64 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.58 cm/s |
Log Po/w (iLOGP) : | 2.52 |
Log Po/w (XLOGP3) : | 4.07 |
Log Po/w (WLOGP) : | 4.77 |
Log Po/w (MLOGP) : | 1.29 |
Log Po/w (SILICOS-IT) : | 7.28 |
Consensus Log Po/w : | 3.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.96 |
Solubility : | 0.0039 mg/ml ; 0.0000109 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.81 |
Solubility : | 0.0000549 mg/ml ; 0.000000154 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -6.02 |
Solubility : | 0.000338 mg/ml ; 0.000000948 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.86 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
90% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous sodium carbonate In ethanol; benzene at 50℃; for 5h; Inert atmosphere; | |
79% | Stage #1: 4,7-dibromobenzo[c][1,2,5]thiadiazole; 5-formylthiophen-2-yl-2-boronic acid With potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate for 0.0833333h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butylphosphonium tetrafluoroborate In tetrahydrofuran; lithium hydroxide monohydrate at 90℃; for 24h; Inert atmosphere; | 2.2.3. Synthesis of BT-Th-CHO [25] Under a nitrogen atmosphere, 4,7-dibromo-2,1,3- benzothiadiazole (147 mg, 0.5 mmol, 1.0 eq.), 5-formyl-2- thiopheneboronic acid (202 mg, 1.3 mmol, 2.6 eq.) and K 2 CO 3 (1.0 g, 7.25 mmol, 14.5 eq.) were dissolved in a mixture of THF (8 mL)/H 2 O (2 mL) and stirred for 5 min. Then, Pd 2 (dba) 3 (23 mg, 0.025 mmol, 0.05 eq.) and (t-Bu) 3 PBF 4 (21 mg, 0.1 mmol, 0.2 eq.) were added, and the mixture was vigorously stirred at 90 C for 24 h. After cooling to room temperature, the reaction mixture was filtered and then washed with water, CH 2 Cl 2 and ethanol to yield BT-Th-CHO (140 mg, 79%) as an orange-red solid. 1 H NMR (400 MHz, CDCl 3 ) δ10.00 (s, 2H), 8.26 (d, J = 3.3 Hz, 2H), 8.06 (s, 2H), 7.87 (d, J = 4.1 Hz, 2H) ppm. |
64% | With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; benzene at 50℃; for 4h; |
60% | With tetrakis-(triphenylphosphine)-palladium In ethanol; lithium hydroxide monohydrate; toluene at 50℃; for 4h; Inert atmosphere; Alkaline conditions; | 2.2.1. Synthesis of 5,5'-(benzo[c]thiophene-4,7-diyl) bis(thiophene-2-carbaldehyde) (1) Compound 1 was synthesized with modification of the publishedprocedure [30]. To a solution of 4,7-dibromobenzo[c]thiophene (294 g,1.0 mmol) and tetrakis(triphenylphosphine)palladium (115.53 mg0.1 mmol) in toluene (12 mL), an ethanol (4 mL) solution of 5-formylthiophene-2-ylbronic acid (400 mg, 2.5 mmol) and aqueous 2Msodium carbonate solution (5 mL) were added at room temperatureunder argon. After the mixture was heated at 50 °C for 4 h, the reactionmixture was cooled, and the formed precipitate was filtered off, thenwashed with water, methanol, and methylene chloride. The precipitatewas further dried and collected as orange solid. The solid was purifiedby recrystallization with chloroform to give compound 1 with yield60%.FT-IR: 1641.32 cm-1 (-CHO stretch); ESI mass spectrum:C16H8N2O2S3 [M+H] + Theo. M/Z = 356.698 [M+H] +, Found. M/Z 356.981.086, Error = -1.132 ppm. |
40% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); Cs2CO3 In ethanol; lithium hydroxide monohydrate; toluene Inert atmosphere; Reflux; | |
With Pd(PPh<SUB>3</SUB>)Cl<SUB>2</SUB>; potassium carbonate In tetrahydrofuran; ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium hydroxide In dimethyl sulfoxide at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium hydroxide In dimethyl sulfoxide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium tetrahydroborate In tetrahydrofuran for 5h; Reflux; | |
With sodium tetrahydroborate In tetrahydrofuran at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran / 50 °C 2: thionyl chloride / toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / tetrahydrofuran / 50 °C 2: thionyl chloride / toluene 3: 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With toluene-4-sulfonic acid In chloroform at 60℃; Inert atmosphere; | |
80% | With toluene-4-sulfonic acid In chloroform at 60℃; Inert atmosphere; | EXAMPLES In a study inventors have synthesized two azomethine- based small molecules via a simple condensation reaction (Fig FontWeight="Bold" FontSize="10" ure 1) . 4-Aminotriphenylamine (TPA, 1) was reacted with two conjugated dialdehydes. 2 , 5-Thiophenedicarbaldehyde (Th, 2a) was used since thiophenes have been studied extensively and possess good charge transport properties. Besides that, both materials are readily available from commercial sources. 4,7- Bis ( 5-formylthiophen-2yl ) -2 , 1 , 3-benzothiadiazole (TBT, 2b) was used because it is found to have a large overlap with the so FontWeight="Bold" FontSize="10" lar spectrum, high mobilities and good film-forming abilities. The reaction was performed in chloroform and p-toluene sul FontWeight="Bold" FontSize="10" fonic acid was used as a catalyst. The products (3a-b) were precipitated, and treated with diluted triethylamine to neu FontWeight="Bold" FontSize="10" tralize the azomethine bond. The small molecules were obtained in good yields (>80%) and characterized using 1H and 13C NMR, FTIR, and mass spectrometry where possible. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: 5-bromo-2-thiophencarboxaldehyde; 4,7-bis-pinacolato-diborane-2,1,3-benzothiadiazole With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) at 80℃; for 24h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.18 g | With piperidine In ethanol; dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 18-crown-6 ether; potassium carbonate / 8 h / 70 °C / Inert atmosphere 2: ammonium acetate; acetic acid / 3 h / 118 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 18-crown-6 ether; potassium carbonate / 8 h / 70 °C / Inert atmosphere 2: ammonium acetate; acetic acid / 12 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 18-crown-6 ether; potassium carbonate at 70℃; for 8h; Inert atmosphere; | 2.2.4. Synthesis of (E)-5-(7-(5-(2,4,6-trimethoxystyryl) thiophen-2-yl)benzo[c]thiophen-4-yl) thiophene-2-carbaldehyde (4) The mixture of compound 1 (0.354 g, 1 mmol), 18-crown-6 (15 mg,0.05 mmol), K2CO3 (276 mg, 2 mmol) was charged sequentially in athree-necked flask and then dried in vacuo for 30 min. A mixture ofadduct 3 (0.523 g, 1.00 mmol) in dried DMSO (30 mL) was addeddropwise to the mixture of over 3 h at 70 °C under Argon atmosphere.The reaction mixture was stirred for a further 5 h at 70 °C, then wasquenched with water and extracted with CH2Cl2. The organic layer wasdried with anhydrous MgSO4. Silica gel chromatography with CH2Cl2gave aldehyde 4. 1H NMR: (400 MHz, DMSO-d6) δ 10.05 (s, 1H), 7.98 (d, 1H), 7.90(d, 1H), 7.75 (d, 1H), 7.65 (d, 1H), 7.25 (d, 1H), 7.08 (d, 1H), 6.79 (d,1H), 6.25 (s, 2H), 3.95 (s, 6H), 3.80 (s, 3H). FT-IR: 2960.25, 2927.73.13cm-1 (-CH3 stretch), 1660.78 cm-1 (-CHO stretch); ESI mass spectrum:C24H20O4S3 [M+H] +Theo. M/Z =521.0658 [M+H] +, Found. M/Z521.0652, Error = - 0.987 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium-t-butoxide In tetrahydrofuran at 90℃; for 24h; Inert atmosphere; | 2.2.5. Synthesis of BT-Th-TPE Under a nitrogen atmosphere BT-Th-CHO (125 mg, 0.35 mmol, 1.0 eq.), TPE-CN (273 mg, 0.74 mmol, 2.1 eq.) and KO t Bu (100 mg, 0.9 mmol, 2.5 eq.) were dissolved in THF (6 mL) and dry ethanol (6 mL), and the mixture was vigorously stirred at 90 C for 24 h. After cooling to room temperature, the reaction mixture was filtered and washed with ethanol. The residue was further recrystallized in a mixture of CHCl 3 and hexane to yield BT-Th-TPE (520 mg, 87%) as a dark-red solid. Melting point: 290 °C. 1 H NMR (400 MHz, CDCl 3 ) δ8.22 (d, J = 4.0 Hz, 2H), 7.98 (s, 2H), 7.71 (d, J = 4.3 Hz, 2H), 7.61 (s, 2H), 7.42 (d, J = 8.5 Hz, 4H), 7.22 -6.95 (m, 34H) ppm. 13 C NMR (100 MHz, CDCl 3 ) δ152.4, 144.9, 143.4, 143.3, 143.2, 142.1, 139.9, 139.2, 133.4, 133.0, 132.1, 131.7, 131.4, 131.3, 131.3, 128.6, 127.9, 127.9, 127.7, 126.9, 126.7, 126.7, 126.3, 125.9, 125.0, 118.2, 108.4 ppm. MS (FTMS + p) m/z: calcd for C 72 H 46 N 4 S 3 1063.2957; found 1063.2935 [M + H] + . |