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CAS No. : | 3839-48-3 | MDL No. : | MFCD00182497 |
Formula : | C7H5ClO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MTHNMAUDCHXFMM-UHFFFAOYSA-N |
M.W : | 140.57 | Pubchem ID : | 19691 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 7 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 37.72 |
TPSA : | 17.07 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) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | 1.51 |
Log Po/w (WLOGP) : | 1.7 |
Log Po/w (MLOGP) : | 1.61 |
Log Po/w (SILICOS-IT) : | 2.62 |
Consensus Log Po/w : | 1.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.24 |
Solubility : | 0.812 mg/ml ; 0.00578 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.48 |
Solubility : | 4.69 mg/ml ; 0.0334 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.31 |
Solubility : | 0.0688 mg/ml ; 0.00049 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.39 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H302-H314-H317-H334 | Packing Group: | Ⅲ |
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 |
---|---|---|
94% | With thionyl chloride In benzene for 1.5h; Heating; | |
94% | With thionyl chloride In benzene at 95℃; for 2.5h; Inert atmosphere; | |
93% | With thionyl chloride In toluene at 120℃; for 1.5h; | 1 The specific synthesis steps are as follows: (1) tropolone ring S1 (10g, 81.9mmol) was dissolved in 250mL of toluene,Then add thionyl chloride (10.7 g, 90 mmol),A white solid precipitated.The reaction temperature was raised to 120 ° C and refluxed for 1.5 h.The white solid disappeared and the solution turned red.Excessive dichlorosulfoxide and toluene were distilled off under reduced pressure.Obtained as a brown solid, which was obtained by column chromatography [V ( petroleum ether): V (ethyl acetate) = 5:1]Then add petroleum ether reflux,The petroleum ether was distilled off under reduced pressure to give a white solid S 210.5 g.The yield was 93%. |
91% | With thionyl chloride In benzene Reflux; | |
86% | Stage #1: 2-hydroxy-2,4,6-cycloheptatrien-1-one With thionyl chloride In toluene Stage #2: In toluene at 120℃; for 1.5h; | |
81% | With thionyl chloride In benzene at 80℃; for 3h; | |
73% | With thionyl chloride for 1.5h; Reflux; | Preparation of 2-chlorotropone VI Tropolone (1.01 g, 8.27 mmol) was dissolved in benzene (25 mL), and then thionyl chloride (0.7 mL, 9.64 mmol) was added and refluxed for 1.5 h. The solution was evaporated; the solid was washing with hexane. The solid was purified by silica gel column chromatography (with AcOEt: hexane = 3: 7 v/v) followed by recrystallization with hexane. The white needles were obtained (0.84 g, 73%). VI: white needles, yield: 73 %, m.p. 64.3-65.0°C (lit.8): yield: 94 %, m.p. 64.0-65.0°C) 1H NMR (300 MHz, CDCl3) d 7.04-7.25 (m, 3H), 7.34-7.41(m, 1H), 7.93 (d, J = 9.3 Hz, 1H) |
With thionyl chloride | ||
With phosphorus trichloride | ||
With trichlorophosphate In N,N-dimethyl-formamide | ||
With thionyl chloride In benzene | 1.15 (15) (15) 2-Thiocyanatotropone STR7 To a solution of tropolone (1,680 mg) dissolved in benzene (36 ml) is added thionyl chloride (1.12 ml). The mixture is stirred for 1.5 hr with refluxing. After concentrating the reaction mixture under reduced pressure, the resulting residue is purified by silica gel chromatography and recrystallized from cyclohexane to give 1.08 g of 2-chlorotropone as yellow needles. | |
With thionyl chloride | ||
With thionyl chloride In benzene for 1.5h; Reflux; | ||
With thionyl chloride In benzene at 80℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium In ethanol at 5 - 10℃; for 4h; | |
With ethanol; sodium ethanolate | ||
With sodium ethanolate In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With triethylamine In tetrahydrofuran at 100℃; for 20h; | |
36% | With triethylamine In tetrahydrofuran at 100 - 110℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With triethylamine In tetrahydrofuran at 120℃; for 18h; | |
25% | With triethylamine In tetrahydrofuran at 100℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With triethylamine In tetrahydrofuran at 100℃; for 20h; | |
49% | With triethylamine In tetrahydrofuran at 100 - 110℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium hydroxide In methanol at -5 - 0℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium In ethanol at 20℃; for 72h; | |
36% | With ethanol; sodium at 20℃; for 72.15h; | Preparation of diethyl 2-Hydroxyazulene-1,3-dicarboxylate VII After preparation of sodium ethoxide, that sodium (1.10 g, 47.8 mmol) was added to ethanol (75 mL) and stirring for 30 min at room temperature, VI (1.05 g, 7.47 mmol) and diethyl malonate (3.8 mL, 24.9 mmol) was added and stirring for 10 min at room temperature, followed by standing for 72 h. After water added, the precipitation was filtration. The solid was dissolved in acetic acid and added water followed by extraction of chloroform. The organic layer was washing with water (3 times) and dried over MgSO4. The solution was filtration and evaporation. The solid was recrystallization with ethanol; the orange crystals were obtained (0.772 g, 36%). VII: orange crystal, yield: 36 %, m.p. 94.5-95.2°C (lit.8): yield: 50 %, m.p. 95.0°C) 1H NMR (300 MHz, CDCl3) d 1.49 (t, J = 7.2 Hz, 6H), 4.52 (q, J = 7.2 Hz, 4H), 7.67-7.74 (m, 3H), 9.37-9.39 (m, 2H), 11.78 (s, 1H). |
With sodium ethanolate |
With sodium ethanolate In ethanol at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate; triethylamine In 1,4-dioxane at 90℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium carbonate; triethylamine In 1,4-dioxane at 90℃; for 20h; | |
83% | With <i>tert</i>-butylamine In ethanol at 20℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With <i>tert</i>-butylamine In ethanol at 20℃; for 40h; | |
85% | With potassium carbonate; triethylamine In 1,4-dioxane at 90℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With <i>tert</i>-butylamine In ethanol at 20℃; for 40h; | |
49% | With potassium carbonate; triethylamine In 1,4-dioxane at 90℃; for 28h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; triethylamine In 1,4-dioxane at 90℃; for 1h; | |
71% | With <i>tert</i>-butylamine In ethanol at 20℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate; triethylamine In 1,4-dioxane at 90℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With <i>tert</i>-butylamine In methanol at 20℃; for 24h; | |
With <i>tert</i>-butylamine In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With <i>tert</i>-butylamine In methanol at 20℃; for 24h; | |
With <i>tert</i>-butylamine In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With <i>tert</i>-butylamine In ethanol at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaN3 / dimethylsulfoxide 2: H2 / Pd-C / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: 2-chlorotropone With (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one palladium(II) complex; phosphoramidite ligand L5 In toluene Inert atmosphere; Stage #2: 3-acetoxy-3-cyano-2-trimethylsilylmethylpropene In toluene at 0 - 4℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran; water at 75℃; for 16h; Inert atmosphere; | |
99% | With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran; water at 75℃; for 16h; Inert atmosphere; | E MO-R-PHE General procedure: MO-R-PHE Rf (0.5, 1 : 1 EtOAc:Hexanes), Mp (77.9-79.2 °C), >99 % yield. IR (KBr): v: 3101, 3022, 1895, 1808, 1625, 1547, 1441, 1261, 784, 698. H1 NMR (500 MHz, CDC13) δ 7.51- 7.49 (m, 2H), 7.43-7.36 (m, 4H), 7.20 (d, J = 12.2 Hz, 1H), 7.14 (ddd, J = 19.8, 1.3, 1.3, 1.3, 1.4 Hz, 1H), 7.07-7.03 (m, 1H), 6.99-6.95 (m, 1H). C13 NMR (126 MHz, CDC13) δ 186.4, 152.4, 142.2, 139.9, 136.5, 135.2, 133.7, 133.2, 129.0, 128.3, 128.0. HRMS (ESI) calcd for Ci3HuO [M+H]+: 183.0810; found: 183.0788. General Procedure E - Suzuki Coupling 2-Chloro-2,4,6-cycloheptatrien-l-one (1.0 eq), aryl boronic acid (2.0 eq), and cesium carbonate (4.0 eq) were added to 10: 1 THF/H2O (0.2 M) and the mixture was thoroughly degassed by bubbling argon through solution (10 min). Bis(triphenylphosphine)palladium(II) dichloride (0.1 eq) was added and the mixture was again degassed with argon. The homogenous solution was heated at 75 °C for 16 h before being cooled to room temperature. Water was added and the mixture was extracted with EtOAc (3 x 15 mL). The combined organic layers were washed with brine (25 mL), dried over Na2S04, filtered and concentrated in vacuo. Flash chromatography of the crude residue (S1O2, EtOAc in hexanes) provided the nes. |
95% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 75℃; |
95% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 75℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran; water at 75℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran; water at 75℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran; water at 75℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tin(IV) chloride In dichloromethane at 20℃; for 16h; Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With trifluoroacetic acid In para-xylene at 20℃; for 24h; diastereoselective reaction; | |
87% | With trifluoroacetic acid In para-xylene at 20℃; for 24h; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With trifluoroacetic acid In para-xylene at 20℃; for 24h; diastereoselective reaction; | |
97% | With trifluoroacetic acid In para-xylene at 20℃; for 24h; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With trifluoroacetic acid In para-xylene at 20℃; for 24h; diastereoselective reaction; | |
97% | With trifluoroacetic acid In para-xylene at 20℃; for 24h; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With sodium ethanolate In ethanol at 20℃; | |
53% | With sodium In ethanol at 20℃; Inert atmosphere; | |
49% | With sodium In ethanol at 20℃; for 12h; | 2 (2) Dissolving sodium (4.0 g, 174 mmol) in 120 mL of absolute ethanol,Further compound diethyl 1,3-acetone dicarboxylate (4.34 g, 21.5 mmol) was added.A milky white solution was obtained.A solution of S2 (2.0 g, 14.3 mmol) dissolved in 10 mL of absolute ethanol was quickly added to the above system.The system turns into a brick red solution.After stirring the reaction for 12 h at room temperature,Add 200 mL of water, precipitate with an orange solid, then filter.Obtained an orange solid, which was then dissolved in 30 mL of glacial acetic acid and diluted with 100 mL of water.Extract three times with dichloromethane, combine the organic phases, and concentrate.Column chromatography [V (petroleum ether): V (ethyl acetate) = 5: 1] to give an orange-yellow solid was isolated S3 2.03g,The yield was 49%. |
38% | Stage #1: diethyl 1,3-acetonedicarboxylate With ethanol; sodium Stage #2: 2-chlorotropone at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With triethylamine In ethanol for 5h; Reflux; | 3 2.3. Preparation of 2,2'-[{1,3-phenylenebis(methylene)}bis(azanediyl)]ditropone (2) 2.3 Preparation of 2,2'-[{1,3-phenylenebis(methylene)}bis(azanediyl)]ditropone (2) A mixture of 2-chlorotropone (0.843 g, 6.00 mmol), 3-(aminomethyl)benzylamine (0.409 g, 3.00 mmol) and triethylamine (1.0 mL, 7.2 mmol) was refluxed in boiling ethanol for 5 h. The reaction mixture was subsequently separated by column chromatography (NH silica, ethyl acetate) to give 2 (0.379 g, 37%) as a yellow solid. Characterization of the product generated the following data: mp 165.5-166.5 °C; IR (KBr): 3257, 3044, 3006, 2923, 2863, 1591, 1548, 1508, 1452, 1403, 1354, 1259, 1215, 1111, 1029, 954, 876, 723, 687 cm-1; 1H NMR (CDCl3, 500 MHz): δ 4.54 (d, J = 5.9 Hz, 4H, -CH2-), 6.49 (d, J = 10.3 Hz, 2H, H7), 6.68 (dd, J = 9.4, 9.4 Hz, 2H, H5), 7.15 (ddd, J = 10.3, 9.4, 1.0 Hz, 2H, H6), 7.18 (d, J = 11.7 Hz, 2H, H3), 7.24 (s, 1H, H2 in benzene ring), 7.26 (d, J = 7.8 Hz, 2H, H4, H6 in benzene ring), 7.27 (ddd, J = 11.7, 9.4, 1.0 Hz, 2H, H4), 7.34 (dd, J = 7.8, 7.8 Hz, 1H, H5 in benzene ring), 7.59 (br-s, 2H, NH); 13C NMR (CDCl3, 125 MHz): δ 176.9 (C1), 155.2 (C2), 137.32 (C4), 137.25 (C1, C3 in benzene ring), 136.1 (C6), 129.5 (C5 in benzene ring), 129.2 (C3), 126.6 (C4, C6 in benzene ring), 126.1 (C2 in benzene ring), 122.8 (C5), 109.1 (C7), 46.8 (CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tris-(dibenzylideneacetone)dipalladium(0); 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl; caesium carbonate In 1,4-dioxane at 100℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With BF4(1-)*C21H22N3O(1+); triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 72h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With BF4(1-)*C21H22N3O(1+); triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 72h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With BF4(1-)*C21H22N3O(1+); triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 72h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With BF4(1-)*C21H22N3O(1+); triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 72h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With BF4(1-)*C21H22N3O(1+); triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 72h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With BF4(1-)*C21H22N3O(1+); triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 72h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With BF4(1-)*C21H22N3O(1+); triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 72h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 54 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 75 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 64 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 61 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 58 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 56 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 85 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 67 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 85 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84 % ee | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-SITCP In toluene at 50℃; for 48h; Inert atmosphere; Overall yield = 70 percent; stereoselective reaction; | General procedure for higher-order cycloaddition of tropone with γ-methylidene-δ-valerolactone. General procedure: To an oven-dried Schlenk tube was added Pd2(dba)3*CHCl3 (0.0025 mmol; 2.6 mg; 2.5 mol%), ligand (5-10 mol%) and 1 ml toluene under an argon atmosphere. The solution was stirred at 24 °C for 30 min, followed by the addition of tropone 1a (0.1 mmol; 10 μl; 1.0 equiv.) and γ-methylidene-δ-valerolactone 2a (0.15 mmol; 37 mg; 1.5 equiv.). Then, the reaction mixture was stirred at 24 °C for 48 h and directly purified by silica gel chromatography (hexane:ethyl acetate = 40:1-20:1) to yield the products in pure form. The optimized conditions for three cycloadducts 3a, 4a and 5a are shown in Extended Data Fig. 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; Inert atmosphere; | 1 Example 1 Under an inert atmosphere (nitrogen), 2,6-dibromo-4-methylaniline (2.8 g, 7.1 mmol), 2-chloro-2,4,6-cycloheptatrien-1-one (1.0 g, 7.1 mmol), cesium carbonate (3.2 g, 10.0 mmol) and 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (44.2 mg, 7.1 umol), tris(dibenzylideneacetone)dipalladium ( 36.8 mg, 3.55 umol) was dissolved in toluene (50 mL), then stirred at 90°C for more than 24 hours.After the reaction was completed, dichloromethane (50 mL) was poured into the black-red liquid mixture, and the insolubles were filtered off.The organic layer was washed with water, separated and dried over anhydrous sodium sulfate.After filtering the solid, the organic phase was concentrated by rotary evaporation in vacuo.The resulting residue was purified by flash column chromatography (silica gel; petroleum ether/ethyl acetate = 3:1) to give 1.8 g (70% yield) of product A as a brown powder. |
Tags: 3839-48-3 synthesis path| 3839-48-3 SDS| 3839-48-3 COA| 3839-48-3 purity| 3839-48-3 application| 3839-48-3 NMR| 3839-48-3 COA| 3839-48-3 structure
[ 695-99-8 ]
2-Chlorocyclohexa-2,5-diene-1,4-dione
Similarity: 0.83
[ 695-99-8 ]
2-Chlorocyclohexa-2,5-diene-1,4-dione
Similarity: 0.83
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