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CAS No. : | 2510-03-4 | MDL No. : | MFCD00089254 |
Formula : | C13H10N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZEJZIWLBVDFZEK-UHFFFAOYSA-N |
M.W : | 194.23 g/mol | Pubchem ID : | 3586445 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.23 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 58.11 |
TPSA : | 47.58 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.75 cm/s |
Log Po/w (iLOGP) : | 2.07 |
Log Po/w (XLOGP3) : | 2.45 |
Log Po/w (WLOGP) : | 2.82 |
Log Po/w (MLOGP) : | 1.76 |
Log Po/w (SILICOS-IT) : | 3.02 |
Consensus Log Po/w : | 2.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.88 |
Solubility : | 0.254 mg/ml ; 0.00131 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.09 |
Solubility : | 0.157 mg/ml ; 0.000808 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.71 |
Solubility : | 0.0377 mg/ml ; 0.000194 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.4 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
100% | With aluminum oxide Inert atmosphere; Neat (no solvent); | |
93% | With ammonium acetate; acetic acid In toluene for 10h; Reflux; Dean-Stark; | |
89% | With 1-butyl-3-methylimidazolium hydroxide at 25 - 30℃; for 0.666667h; |
88% | With ammonium acetate; acetic acid In toluene Heating; | |
87% | With ammonium acetate; acetic acid In toluene for 6h; Dean-Stark; Reflux; | Synthesis of α,α-dicyanoolefins 2a-c In a 50 mL two-way flask were added toluene (30 mL), malonitrile (1.72 g, 26 mmol), α-tetralone (2.66 mL, 20 mmol), ammonium acetate (0.33 g, 4,28 mmol) and glacial acetic acid (2 mL). With the aid of a Dean-Stark apparatus for water removal, the reaction was refluxed for 6 hours. The solvent was then evaporated. 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile (2a): The product was obtained as a green solid after purification by washing with ice-cold ethanol in 87% yield (3.39 g, 17.45 mmol). 1H NMR (400 MHz, CDCl3) δ: 8.14 (dd, J = 8.0, 0.7 Hz, 1H), 7.43 (td, J = 7.5, 1.3 Hz, 1H), 7.32-7.25 (m, 1H), 7.24-7.19 (m, 1H), 3.04-2.91 (m, 2H), 2.82 (t, J = 6.3, 2H), 2.00-1.88 (m, 2H). 13C NMR (100 MHz, CDCl3) δ: 172.6; 142.0; 133.7; 130.0; 129.5; 128.0; 126.9; 114.0; 113.4; 79.8; 33.1; 29.7, 22.2. |
76% | With ammonium acetate; acetic acid In toluene for 4h; Reflux; Dean-Stark; Inert atmosphere; | |
71% | With ammonium acetate; acetic acid In benzene at 130℃; Dean-Stark; | |
65% | ||
45% | With ammonium acetate; acetic acid In toluene for 24h; Reflux; | |
42% | With ammonium acetate; acetic acid In toluene Reflux; Dean-Stark; | |
With ammonium acetate; acetic acid; benzene unter Entfernen des entstehenden Wassers; | ||
With ammonium acetate; acetic acid | ||
With ammonium acetate; acetic acid In benzene for 24h; Heating; | ||
With ammonium acetate; acetic acid In benzene for 18h; Heating; | ||
With aluminum oxide | ||
With ammonium acetate; acetic acid In toluene Heating; | ||
With ammonium acetate; acetic acid In toluene Reflux; | ||
With [BmIm]OH In ethanol Reflux; | ||
Alkaline conditions; Inert atmosphere; Glovebox; | ||
With ammonium acetate; acetic acid In toluene for 24h; Reflux; | ||
With ammonium acetate; acetic acid In toluene Dean-Stark; Reflux; | 1. General procedures for the preparation of vinyl malononitrile General procedure: In a 100 mL round-bottomflask wasplaced with 40 mL toluene containing ammonium acetate (1000 mg) and glacialacetic acid (3 mL). Then malononitrile (30 mmol) and the ketone (33 mmol) wereadded and the reaction was refluxed and stirred vigorously, the water formed inthe reaction was removed by a Dean and Stark trap placed under the refluxcondenser. After the completion of the reaction, the mixture was cooled toambient temperature and diluted with EtOAc, then washed with brine. The organicphase was dried over Na2SO4 and the solvent wasevaporated under reduced pressure. The residue was recrystallized from ethanolcrystallization or chromatography to give pure products. | |
With ammonium acetate; acetic acid In toluene Reflux; Dean-Stark; | ||
With triethylamine In ethanol at 20℃; for 2h; | General procedure for synthesis of methylenemalononitriles General procedure: Malononitrile (9.5 mmol) and the aldehyde (9.5 mmol) were dissolved in 5 mL of EtOH in a 50 mL flask, followed by adding one drop of triethylamine. After stirring at room temperature for 2 h, filtrate the solid to give the crude products. Further purification was completed by flash chromatography. | |
With ammonium acetate; acetic acid In toluene Reflux; Dean-Stark; | ||
With ammonium acetate; acetic acid In toluene at 110℃; | 1 step 1: Compound 1-tetralone C1 (2.9 g, 20 mmol)And malononitrile (2.6 g, 40 mmol) was added to the reaction unit with a water separator.Toluene (10 ml) was added to the device as a solvent.Ammonium acetate (3.8 g, 50 mmol) was dissolved in acetic acid (5.5 ml, 100 mmol), added to the reaction apparatus, heated to reflux (110 ° C), and then cooled to room temperature after completion of the reaction.Extract with diethyl ether and dry the organic phase with Na2SO4.The crude compound S1 was obtained by spin-drying, and the next step was carried out without purification; | |
With ammonium acetate In acetic acid Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium fluoride; natural phosphate; trichlorophosphate at 70 - 80℃; for 3h; | |
62% | With trichlorophosphate at 20 - 80℃; for 3.5h; | General procedure for the synthesis of 2-chloro-3-cyanopyridines 4 General procedure: To a flask containing 10 mmol of a gem-dicyanoalkene 1 and 20 mmol (3.0 g) of POCl3 in DMF (10 mL), 0.1 g of phosphate catalyst (KF/NP) was added, and the mixture was stirred at room temperature for 30 min. Then the bath temperature was slowly raised to 70 - 80 °C. The reaction mixture was heated for 3 h and after cooling poured into cold water. The formed solid was filtered and recrystallized or purified by column chromatography. |
With trichlorophosphate at 80℃; for 3h; |
With trichlorophosphate at 70 - 80℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In acetone at -40℃; for 38h; | |
83% | With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea In toluene at 5℃; for 60h; enantioselective reaction; | II. General procedure for asymmetric vinylogous Michael addition of vinyl malononitriles to nitrostyrene General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium phosphate In toluene at -25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: dimethyl acetylenedicarboxylate; malononitrile With triethylamine In ethanol at 20℃; for 0.333333h; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In ethanol | Dialkyl 5-Amino-4,6,6-tricyano-1-(2-methoxy-2-oxoethyl)cyclohexa-2,4-diene-1-carboxylates (3); General Procedure General procedure: A mixture of malononitrile (1.0 mmol), dialkylacetylenedicarboxylate 2 (1.0 mmol), and Et3N (one drop) in EtOH (5 mL) was stirred at r.t. for 20 min. A solution of α,α-dicyanoolefin 1 (1.0 mmol) and Et3N (1 mmol) in EtOH (3 mL) was then added. When the reaction was complete, the solvent was removed under reduced pressure and the residue was purified by column chromatography [silica gel,hexane/EtOAc, (1:8)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | General procedure: To a solution of α,α-dicyanoolefin 1 (1 mmol) and ketenedithioacetal 2 (1 mmol) in EtOH (3 mL) was added Et3N (1mmol), and the solution was stirred for 30 min at r.t. Then,excess hydrazine was added to mixture. Upon completion(2 h, monitoring by TLC), the mixture was filtered and theprecipitate washed with EtOH (2 × 4 mL) to afford the pureproducts 3a,b,e,f and 4a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In ethanol at 20℃; for 10h; | General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With triethylamine In ethanol at 20℃; for 10h; | General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine In ethanol at 20℃; for 10h; | General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With triethylamine In ethanol at 20℃; for 10h; | General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With <i>L</i>-proline In ethanol; water at 20℃; for 4h; Green chemistry; | Experimental procedure for the synthesis of 6a-e General procedure: 3-(2-Oxo-2-phenylethylidene)indolin-2-one1 5 (1 mmol) and alkylidene malononitrile 3a-e (1 mmol) were stirred in a mixture of EtOH:H2O (2:1) in the presence of L-proline (15 mol%) at room temperature for 3 h. The solid precipitated out was filtered off and recrystallized from methanol to afford product 6a-e as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea; In toluene; at 5℃; for 60h; | General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea In toluene at 5℃; for 60h; enantioselective reaction; | II. General procedure for asymmetric vinylogous Michael addition of vinyl malononitriles to nitrostyrene General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea In toluene at 5℃; for 60h; enantioselective reaction; | II. General procedure for asymmetric vinylogous Michael addition of vinyl malononitriles to nitrostyrene General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
49% | With triethylamine In acetonitrile at 50℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 7 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: (2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 9 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: trans-4'-(trifluoromethyl)chalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 12 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 4'-bromo-4-methoxy-<i>trans</i>-chalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 13 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: (E)-1-phenyl-3-(thiophen-2-yl)-2-propen-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 16 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 1,3-diphenyl-propen-3-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 1 4.3. Synthesis of Michael adducts 4a-x In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. 4.3.1. 2-((S)-2-((R)-3-oxo-1,3-diphenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile (4a). The product was obtained as a white solid in 61% yield (122 mg, 0.3 mmol) after purification by chromatography column using 95: 5 Hexane-EtOAc as eluent. 1H NMR (400 MHz, CDCl3) δ: 8.03 (d, J = 7.4 Hz, 1H), 7.74 (dd, J = 8.3, 1.1 Hz, 2H), 7.62-7.48 (m, 2H), 7.43-7.34 (m, 3H), 7.32 (dd, J = 4.2, 3.4 Hz, 5H), 7.25-7.19 m, 1H), 3.66 (dt, J = 11.2, 3.5 Hz, 1H), 3.53 (dd, J = 16.4, 9.6 Hz, 1H), 3.40 (ddd, J = 4.14, 9.70, 11.17 Hz, 1H), 3.08 (ddd, J = 16.5, 11.9, 4.8 Hz, 2H), 2.83 (dd, J = 19.0, 6.5 Hz, 1H), 2.03-1.86 (m, 1H), 1.77 (ddd, J = 9.0, 6.5, 3.2 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ: 197.1; 177.3; 140.9; 140.1; 136.4; 134.1; 133.3; 130.0; 128.9; 128.8; 128.7; 128.6; 128.0; 127.9; 127.4; 127.0; 113.8; 113.6; 80.5; 47.5; 43.2; 41.7; 25.7; 24.4. ee: 96% measured by UPC2 on a Trefoil AMY1 column, CO2/iPrOH gradient [CO2 (1 min), CO2 at 60:40 (4 min), 60:40 (3 min)], 2 mL/min, 35 °C, 137.89 bar, λ = 250.0 nm, tmajor = 3.448 min, tminor = 3.136 min [α]D22 = -140.3 (c = 0.068, CHCl3). HRMS-ES+ m/z: [M + H]+ calcd for C24H22N2O 403.1805; found 403.1804. IR (λmax): 2233, 1687, 1546 cm-1. mp: 161.4-162.9 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: (E)-4'-nitrochalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 2 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: (E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 3 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: trans-4'-methoxychalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction; | 4 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With cetyltrimethylammonim bromide In water at 20℃; for 24h; | 1; 1-6 Example 1 Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90% |
90% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. 4.2.1. 6-Amino-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile (3aa) White solid; 27.9 mg, 90% yield; mp 182.3-183.1 °C; 1H NMR(300 MHz, DMSO-d6) δ 8.20 (d, J = 7.7 Hz, 1H), 8.07 (d, J = 7.5 Hz, 1H), 7.75 (d, J = 8.3 Hz, 1H), 7.60 (t, J = 7.8 Hz, 1H), 7.49-7.41 (m,1H), 7.41-7.29 (m, 3H), 6.36 (s, 2H), 3.17-3.06 (m, 2H), 2.89-2.78 (m,2H); 13C NMR (75 MHz, DMSO-d6) δ 156.2, 142.0, 138.5, 138.0, 132.1,131.2, 128.5, 127.9, 127.9, 126.6, 126.1, 124.8, 123.7, 123.6, 123.5, 121.8,118.7, 112.1, 88.6, 28.5, 24.3; HRMS (ESI-TOF) calcd. for C21H15N2O [M + H]+ 311.1179; found: 311.1170. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With cetyltrimethylammonim bromide In water at 20℃; for 18h; | Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90% |
90% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 18h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With cetyltrimethylammonim bromide In water at 20℃; for 20h; | Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90% |
87% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 20h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With cetyltrimethylammonim bromide In water at 20℃; for 36h; | Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90% |
87% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With cetyltrimethylammonim bromide In water at 20℃; for 30h; | Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90% |
72% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 30h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With cetyltrimethylammonim bromide In water at 20℃; for 48h; | Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90% |
62% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 48h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 30h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With cetyltrimethylammonim bromide; caesium carbonate; In water; at 20℃; for 36h; | General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 18h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 18h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; | 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sodium tetrahydroborate; oxygen; potassium carbonate In N,N-dimethyl-formamide at 50℃; Molecular sieve; | One-Pot Oxidative Decyanation of Alkylidenemalononitriles to Alcohols; General Procedures A-1 and A-2 General procedure: The corresponding alkylidenemalononitrile (procedure A-1) or alkylmalononitrile (procedure A-2) substrate (1 equiv.) was dissolved in DMF (0.1 M) in a flame-dried Schlenk flask under positive pressure N2 along with 3 Å molecular sieves (~20 mg/mL of solvent). Using an O2 balloon, O2 gas was gently bubbled though the reaction mixture using a long needle through the reaction flask septum. O2 was bubbled for 10 min. After 10 min, NaBH4 (4 equiv. for alkylidenemalononitriles and 2 equiv. for alkylmalononitriles) was then added and the reaction mixture was stirred for 2-5 min (until effervescence stopped). Then, K2CO3 (2 equiv.) was added and the reaction mixture was heated at 50 °C. O2 was bubbled through the mixture until reaction completion. Once completion was achieved (monitored by TLC), the reaction mixture was cooled to rt and the O2 balloon was removed. The excess NaBH4 was slowly quenched with H2O (1 mL) and the reaction mixture was diluted with 2 M HCl(aq) (5 times the reaction volume). The resulting aqueous mixture was extracted with EtOAc three times (2 times the aqueous phase volume). The combined organic layers were washed with 2 M HCl(aq) (equal volume as the organic phase) and brine (equal volume as the organic phase), and dried over Na2SO4. The EtOAc was removed under reduced pressure and the crude was purified via silica gel column chromatography (Hex/EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction; | 7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction; | 7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction; | 7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction; | 7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH. |
Tags: 2510-03-4 synthesis path| 2510-03-4 SDS| 2510-03-4 COA| 2510-03-4 purity| 2510-03-4 application| 2510-03-4 NMR| 2510-03-4 COA| 2510-03-4 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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