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CAS No. : | 583-60-8 | MDL No. : | MFCD00001635 |
Formula : | C7H12O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LFSAPCRASZRSKS-UHFFFAOYSA-N |
M.W : | 112.17 | Pubchem ID : | 11419 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 33.85 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.91 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 1.51 |
Log Po/w (WLOGP) : | 1.77 |
Log Po/w (MLOGP) : | 1.35 |
Log Po/w (SILICOS-IT) : | 2.15 |
Consensus Log Po/w : | 1.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.49 |
Solubility : | 3.66 mg/ml ; 0.0326 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.48 |
Solubility : | 3.74 mg/ml ; 0.0334 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.53 |
Solubility : | 3.3 mg/ml ; 0.0294 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.87 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210 | UN#: | 1224 |
Hazard Statements: | H225-H332 | 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 |
---|---|---|
98% | With oxygen; acetic acid In water at 60℃; for 8h; | |
97% | With oxygen In water at 60℃; for 8h; | |
97% | With oxygen In methanol at 60℃; for 24h; |
97% | With oxygen In water at 60℃; for 8h; | |
90% | With hexaaquaruthenium(II) tosylate; oxygen; acetic acid In water at 55℃; for 24h; | |
87% | With aurin; water; copper(II) bis(trifluoromethanesulfonate) In acetonitrile for 48h; Schlenk technique; Irradiation; | |
86% | With water; oxygen In benzene at 60℃; for 20h; | |
86% | With oxygen; copper dichloride In acetic acid at 80℃; for 5h; | |
77% | With sulfuric acid; K-10 montmorillonite; oxygen In acetic acid at 70℃; for 30h; | 2.4 Catalytic tests General procedure: All catalytic tests were carried out using Schlenk techniques (20 mL) which was attached to a vacuum line with a manometer and a gas inlet. Prior to each catalytic test, the clay was dried at 373 K for 2 h. In a typical experiment, the Schlenk was charged with the solvent (5.0 mL; solvent: CH3CN, H2O, CH3OH, CH3COOH or a mixture of CH3COOH and H2O) and K-10MT (0.20 g). In some tests H2SO4 (0-0.37 mmol) was also added. The substrate (5.0 mmol) was then added and the vessel was immersed in an oil bath preheated at 70 °C. O2 was introduced at atmospheric pressure and the mixture was stirred magnetically for 24 h. Three parallel catalytic experiments were carried out for each test. |
75% | With oxygen In water; acetic acid at 60℃; for 1h; | |
70% | With oxygen; acetic acid In water at 60℃; for 4h; variation of time and AcOH concn.; other cycloalkanones; | |
70% | With oxygen; acetic acid In water at 60℃; for 4h; | |
53% | With 1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate; hydroquinone In chlorobenzene at 60℃; for 48h; | |
44% | With hydrogenchloride; sodium nitrite In tetrahydrofuran; water at -5 - 20℃; for 10h; | |
25% | With oxygen In acetic acid at 65℃; for 69h; | |
With chromium(VI) oxide; sulfuric acid | ||
With potassium permanganate; water | ||
With Adipic acid; air; manganese(II) nitrate at 65℃; | ||
With sulfuric acid; chromic acid Oxydation; | ||
With water; oxygen im Licht; | ||
With oxygen; sodium methylate In methanol; 1,2-dimethoxyethane | ||
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium <i>tert</i>-butylate; oxygen In <i>tert</i>-butyl alcohol | ||
35 %Chromat. | With dihydrogen peroxide In water; <i>tert</i>-butyl alcohol at 80℃; for 24h; | |
With iron(III) chloride; oxygen; dimethyl sulfoxide at 55℃; for 24h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium methylate In toluene at 20℃; Cooling with ice; | 27.27a 2-(hydroxymethylene)-6-methylcyclohexanone To an ice cold suspension of powdered sodium methoxide (24.5 g, 454 mmol) in toluene (450 mL) was added 2-methylcyclohexanone (60 g, 178 mmol) and ethyl formate (79.2 g, 1069 mmol). The mixture was stirred at room temperature overnight. Ice water and toluene were added and the phases were separated. The organic phase was washed with 10% sodium hydroxide (100 mL x 2). The aqueous layer was acidified with dilute hydrochloric acid to pH ~3 and then extracted with diethyl ether (200 mL x 3). The combined organic layer was washed with water (100 mL x 2) and brine (100 mL x 2) and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave the title compound as a light orange oil (50 g, Yield: 66%). |
With sodium In diethyl ether | ||
With sodium methylate 1.) toluene; 2.) H2O; Multistep reaction; |
With potassium <i>tert</i>-butylate In tetrahydrofuran at -10 - 20℃; | ||
Stage #1: formic acid ethyl ester With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 2-Methylcyclohexanone In tetrahydrofuran at -10 - 20℃; for 12.75h; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; Inert atmosphere; | ||
With sodium hydride In methanol; toluene; mineral oil at 0 - 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 51 % Chromat. 2: 4 % Chromat. 3: 35 % Chromat. | With sulfuric acid at 150 - 155℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With oxygen; deuterium at 37.5℃; Irradiation; gas-phase, add of Me3N, var. pressure; further reag: CH4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 1.7% 2: 0.8% 3: 94% | With manganese(II) bromide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane In tetrahydrofuran for 4h; Ambient temperature; | |
1: 94% 2: 0.8% 3: 1.7% | With manganese(II) bromide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane In tetrahydrofuran at 22℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol for 1.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | |
81% | With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | |
78% | With lithium diisopropyl amide In 1,2-dimethoxyethane 1) -78 deg C, 2 hr, 2) 0 deg C, 9 h; |
53% | Stage #1: 2-Methylcyclohexanone With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; toluene at -78 - 20℃; for 6h; Inert atmosphere; | |
53% | With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere; | |
52% | Stage #1: 2-Methylcyclohexanone With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.333333h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; n-heptane; ethylbenzene at -78 - 20℃; for 0.666667h; | 4.3.1 6-Methylcyclohex-1-en-1-yl trifluoromethanesulfonate (13f) A flame-dried two-necked 50-mL flask equipped with a Teflon-coated magnetic stirring bar and a rubber septum was charged with THF (3.0mL). After the flask was cooled to-78°C, LDA (1.5M in THF/heptane/ethylbenzene, 3.7mL, 5.6mmol) was added. To the resulting solution was added 2-methylcyclohexanone (0.61mL, 5.0mmol) in THF (1.0mL) dropwise over 3min, and the resulting solution was stirred at-78°C for 20min. N-Phenyl-bis(trifluoromethanesulfonimide) (1.89g, 5.3mmol) in THF (6.0mL) was added, and the reaction mixture was allowed to warm to room temperature for 40min. After the solution was treated with water and diethyl ether, the resulting mixture was extracted twice with diethyl ether (10mL). The combined organic extracts were washed with 1M aqueous sodium hydroxide and brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a crude material, which was purified by silica gel column chromatography (hexane) to afford the corresponding cyclohexenyl triflate 13f (0.638g, 2.61mmol, 52%) as a colorless oil. Rf=0.26 (hexane); The spectroscopic data were corresponding with those reported in the literature [25]. 1H NMR (400MHz, CDCl3): δ 5.73 (td, 1H, J=4.0, 1.2Hz), 2.60-2.48 (m, 1H), 2.20-2.13 (m, 2H), 1.98-1.88 (m, 1H), 1.72-1.51 (m, 2H), 1.51-1.41 (m, 1H), 1.14 (d, 3H, J=6.8Hz); 13C NMR (100MHz, CDCl3): δ 135.5, 118.7 (q, 1JC-F=318 Ηz), 118.4, 32.5, 31.6, 24.6, 19.3, 17.9; 19F NMR (376MHz, CDCl3): δ-77.3. |
With lithium diisopropyl amide 1) THF, -78 deg C, 2h, 2a) 0 deg C, 3h, 2b) RT, overnight; Yield given. Multistep reaction; | ||
With lithium diisopropyl amide Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium 1.) THF, hexane, -70 deg C, 15 min, 2.) THF, hexane, -70 deg C, 15 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In glacial acetic acid at 60℃; for 8h; Reflux; | 1 Synthesis Example 1 Synthesis of Compound 38 Synthesis of Intermediate 1-a Synthesis Example 1 Synthesis of Compound 38 Synthesis of Intermediate 1-a[0131] Intermediate 1-a was synthesized according to Reaction Scheme 1 below: [0132] 50 g (0.462 mol) of phenylhydrazine and 170 ml of acetic acid were put into a 500 ml round-bottom flask, and the temperature was raised to 60° C. 51.9 g (0.462 mol) of 2-methylcyclohexanone was dropped into the heated flask, and the mixture was refluxed for about 8 hours. After the reaction was completed, 100 ml of water was added to the mixture, and the resultant mixture was made alkaline with sodium hydroxide. Then, the resultant solution was extracted with water and ethyl acetate to separate an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Thereafter, the resulting product was purified by column chromatography using hexane and ethyl acetate as eluents. As a result, 72 g of Intermediate 1-a was obtained (yield: 84%). |
84% | With glacial acetic acid at 60℃; for 8h; Reflux; | 3 Synthesis of Compound 33-1 In 500ml of round bottom flask, a heating phenylhydrazine 50g ( 462mmol ) and 170ml of acetic acid up to 60°C . Heated To the flask was added dropwise 2-methylcyclohexanone 51.9g ( 462mmol ) . When the addition was complete, then reflux for 8 hours . When this reactionis completed after the addition of 100ml of water was basified with sodium hydroxide . Extracted with water and ethyl acetate and the organic layerAfter anhydrous magnesium sulfate and concentrated under reduced pressure treatment , column chromatography using hexane and ethyl acetate as eluant Separated by chromatography , to obtain the compound 33-1 ( 72g , 388.08mmol , 84% yield ) |
84% | With glacial acetic acid at 60℃; for 8h; | 6-1 Synthesis of intermediate 6-a phenylhydrazines (44.3 g, 0.41 mol) were put intothe acetic acid 170 mL and it heated to 60 °C . 2-methylcyclichexanone (45.9 g, 0.41 mol) were dipped as the slowly and it refluxed for 8 hours. After the water 100 mL was added if reaction was concluded it basified with the NaOH. It separated according to the column chromatography after doing the extraction [intermediate 6a]and 63.8 g (yield84%) was obtained from the ethyl acetate |
84% | With glacial acetic acid for 5h; Reflux; | 4 Synthesis Example 4. Synthesis of Compound Represented by [Formula 93] 50 g (0.462 mole) of phenyl hydrazine and 150 mL of acetic acid were added to a 500 mL three-necked round bottom flask and refluxed. 51.9 g (0.462 mole) of 2-methyl cyclohexanone was added dropwise thereto and refluxed for 5 hours. After the reaction was completed by adding 100 mL of water and an aqueous NaOH solution, the organic layer was separated and separated by column chromatography to obtain 4-(1) (72 g, 84%) |
84% | Stage #1: phenylhydrazine With glacial acetic acid at 60℃; Stage #2: 2-Methylcyclohexanone In glacial acetic acid for 8h; Reflux; | 11.11-3 [Reaction 11-3] Synthesis of Intermediate 11-c Phenylhydrazine (44.3 g, 0.41 mol) was added to 170 mL of acetic acid. The mixture was heated to 60° C. To the mixture was slowly added dropwise 2-methylcyclohexanone (45.9 g, 0.41 mol). The resulting mixture was refluxed for 8 h. After completion of the reaction, to the reaction mixture was added 100 mL of distilled water. The mixture was basified with sodium hydroxide and extracted with ethyl acetate. Purification by column chromatography afforded 63.8 g (yield 84%) of Intermediate 11-c. |
84% | With glacial acetic acid at 60℃; for 8h; | 1.1-2 Synthesis Example 1-2-1: Synthesis of Intermediate 1-2-a Intermediate 1-2-a was synthesized according to Scheme 14 below. 50 g (0.462 mol) of phenylhydrazine and 170 ml of acetic acid were added to the reactor and heated to 60 ° C. 51.9 g (0.462 mol) of 2-methylcyclohexanone was added dropwise to the heated flask, followed by reflux for 8 hours.After completion of the reaction, 100 ml of water was added and basified with sodium hydroxide,The organic layer obtained by extraction with water and ethyl acetate was concentrated under reduced pressure by anhydrous treatment with magnesium sulfate,Hexane and ethyl acetate were used as the developing solvent to separate column chromatography to give intermediate 1-2-a (72g, 84% yield). |
84% | With glacial acetic acid for 8h; Reflux; | 7 Synthesis of [Intermediate 7-e] Phenylhydrazine (44.3 g, 0.41 mol) was added to 150 mL of acetic acid and heated to 60°C.2-methylcyclic hexanone (45.9 g, 0.41 mol) was slowly added dropwise and refluxed for 8 hours. When the reaction was completed, 100 mL of distilled water was added and then basified with sodium hydroxide. After extraction with ethyl acetate and separation by column chromatography, 63.8 g (yield 84%) of [Intermediate 7-e] was obtained. |
84% | With glacial acetic acid for 6h; Reflux; | 23-5 Synthesis Example 23-5) Synthesis of [Intermediate 23-e] In a round bottom flask, 40 g (0.3699 mol) of phenylhydrazine, 41.5 g (0.3699 mol) of 2-methylcyclohexanone,After adding 240 ml of acetic acid, the mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was basified with sodium hydroxide. After neutralization by extraction with water and ethyl acetate, the organic layer was anhydrous treated with magnesium sulfate, concentrated under reduced pressure, and then separated by column chromatography using hexane and dichloromethane to give 57.5g of [Intermediate 23-e] obtained (yield 84). %) |
84% | With glacial acetic acid for 8h; Reflux; | 8 Synthesis of [Intermediate 8-a] phenylhydrazine (44.3 g, 0.41 mol) was added to 150 mL of acetic acid and heated to 60 °C. 2-Methylcyclohexanone (45.9 g, 0.41 mol) was slowly added dropwise and refluxed for 8 hours. Upon completion of the reaction, 100 mL of distilled water was added and then basified with sodium hydroxide. After extraction with ethyl acetate and separation by column chromatography, 63.8 g (yield 84%) of [Intermediate 8-a] was obtained. |
84% | With glacial acetic acid for 6h; Reflux; | 1-4 Phenylhydrazine 40g (0.3699mol), 2-methylcyclohexanone 41.5g (0.3699mol), and 240ml of acetic acid were added to a round bottom flask, followed by reflux stirring for 6 hours. After the reaction was completed, the reaction solution was basified with sodium hydroxide. After neutralization by extraction with water and ethyl acetate, the organic layer was anhydrous treated with magnesium sulfate, concentrated under reduced pressure, and then separated by column chromatography using hexane and dichloromethane to obtain 57.5g of [Intermediate 1-d] (yield 84). %) |
84% | With glacial acetic acid at 60℃; for 8h; | 8 Synthesis of [Intermediate 8-a] Phenylhydrazine (44.3 g, 0.41 mol) was added to 150 mL of acetic acid and heated to 60 °C.2-Methylcyclic hexanone (45.9 g, 0.41 mol) was slowly added dropwise and refluxed for 8 hours.When the reaction was completed, 100 mL of distilled water was added, followed by basification with sodium hydroxide.After extraction with ethyl acetate, it was separated by column chromatography to obtain 63.8 g of [Intermediate 8-a] (yield 84%). |
84% | With glacial acetic acid for 6h; Reflux; | 4.4-2 Synthesis of Intermediate 4-c In a 500-ml round-bottom flask, phenylhydrazine (40 g, 0.3699 mol), 2-methylcyclohexanone (41.5 g, 0.3699 mol), and acetic acid (240 ml) were refluxed for 6 hours. After completion of the reaction, the reaction mixture was alkalinized with sodium hydroxide, extracted with water and ethylene acetate, and neutralized. The organic layer was dehydrated over magnesium sulfate, concentrated, and isolated by column chromatography to afford Intermediate 4-c. (57.5 g, 84%) |
81.7% | With glacial acetic acid at 40 - 60℃; | 8.1 (1) Synthesis of Compound Represented by [Formula 182-a] Into a 500 ml round bottom flask, 31 g (277 mmol) of 2-methylcyclohexanone and 170 ml of acetic acid were added.After stirring at 40-60 ° C., 30 g (277 mmol) of phenylhydrazine was added dropwise to the reaction solution.After the addition was completed, the mixture was stirred under reflux and the reaction was completed by TLC. When the reaction was completed, 100 ml of water was added.Sodium hydroxide was added and basified.The reaction solution was extracted with ethyl acetate and hexane, the organic layer was separated, anhydrous treated with magnesium sulfate, concentrated under reduced pressure, separated by column and purified.Obtained compound 42g (yield: 81.7%). |
76% | With glacial acetic acid at 60℃; for 8h; | 9.9-2 Synthesis Example 9-(2): Synthesis of <Intermediate 9-b> 100 g (0.924 mol) of phenyl hydrazine and 500 mL of acetic acid were stirred in the reactor, and then heated to 60°C. 103.6 g (0.924 mol) of 2-methyl cyclohexanone was slowly added dropwise, followed by refluxing for 8 hours. After completion of the reaction, the mixture was extracted with water and ethyl acetate, concentrated, and separated by column chromatography to obtain 130 g of . (Yield 76%) |
76% | With glacial acetic acid at 60℃; for 8h; | 1.1-1 Synthesis Example 1- (1): Synthesis of Intermediate 1-a In a round bottom flask, 100 g (0.924 mol) of phenyl hydrazine and 500 ml of acetic acid were stirred and then heated to 60°C. 103.6 g (0.924 mol) of 2-methyl cyclohexanone was slowly added dropwise, followed by refluxing for 8 hours. After completion of the reaction, extraction was performed with water and ethyl acetate, concentrated, and separated by column chromatography to obtain 130 g of [Intermediate 1-a]. (Yield 76%) |
76% | With glacial acetic acid at 60℃; for 8h; Reflux; | 12-(1) Synthesis Example 12-(1): Synthesis of Intermediate 12- In a round-bottom flask, phenylhydrazine (100 g, 0.924 mol) was stirred together with acetic acid (500 ml) and then the mixture was heated to 60° C. and stirred under reflux while 2-methyl cyclohexanone (103.6 g, 0.924 mol) was dropwise added slowly over 8 hours. After completion of the reaction, extraction and concentration was made with water and ethyl acetate. The concentrate was isolated by column chromatography to afford (130 g, 76%) |
76% | With glacial acetic acid at 60℃; for 8h; | 1-1 Synthesis Example 1-1: Synthesis of Intermediate 1-a In a round bottom flask, 100 g (924 mmol) of phenylhydrazine and 500 mL of acetic acid were stirred and then heated to 60 °C.103.6 g (924 mmol) of 2-methylcyclohexanone was slowly added dropwise, followed by refluxing for 8 hours.After completion of the reaction, the mixture was extracted using water and ethyl acetate, concentrated, and separated by column chromatography to obtain .(130 g, 76%) |
61% | With phosphorus trichloride In benzene for 0.5h; Ambient temperature; | |
50% | ||
With glacial acetic acid Heating; | ||
With glacial acetic acid at 60℃; Yield given; | ||
With glacial acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 5% 2: 1% 3: 89% | With manganese(II) bromide; lithium hexamethyldisilazane In tetrahydrofuran for 14h; Ambient temperature; | |
1: 89% 2: 1% 3: 5% | With manganese(II) bromide; lithium hexamethyldisilazane In tetrahydrofuran at 22℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium amide In tetrahydrofuran for 2h; Heating; | |
83% | Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran; mineral oil for 1.5h; Inert atmosphere; Reflux; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; mineral oil for 0.25h; Inert atmosphere; Reflux; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0 - 25℃; for 3h; Inert atmosphere; | 4.1 In this example 4, 2,2-dimethyl-1 -ethynyl-1 -cyclohexanol was prepared as follows. In a first step, to a 1 L two-neck flask equipped with a water-cooled condenser, was added NaH (60% in mineral oil, 16 gram) and 350 mL anhydrous THF under N2. To this suspension, was added 2-methylcyclohexanone (44 ml). The 2- methylcyclohexanone and the other starting materials were commercially available from Sigma Aldrich. The mixture was heated to reflux for 1 .5 hours. H gas was released in the first 20 minutes), then HMDS (hexamethyldisilazane, 1 1 .4 mL) was added, and the mixture was refluxed for another 15 minutes. After cooling to 0°C, methyl iodide (30 mL) was slowly added to the flask, and the resulting reaction was highly exothermic. The flask was allowed to warm up to room temperature and stirred for 3 hours. THF was removed with a rotary evaporator. To the residue, was added diethyl ether (150 mL). The mixture was filtered, and ether was removed with the rotary evaporate to give the crude, which was further purified by vacuum distillation to give 2,2- dimethylcyclohexanone as a colorless liquid (37.6 gram, 83% yield). |
79% | Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran for 0.25h; Inert atmosphere; Reflux; Stage #3: methyl iodide In tetrahydrofuran at 0 - 23℃; for 3h; Inert atmosphere; |
75% | With potassium hydride | |
55% | Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran; mineral oil for 1h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; mineral oil for 0.25h; Schlenk technique; Inert atmosphere; Reflux; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 2.16667h; Schlenk technique; Inert atmosphere; | |
33% | With sodium amide In tetrahydrofuran Reflux; | |
With triethyl borane; potassium hydride THF, room temp.; Yield given. Multistep reaction; | ||
With sodium hydride Yield given; | ||
With triethyl borane; potassium hydride 1.) THF, 12 h, 25 deg C; 2.) 10 h, THF; Yield given. Multistep reaction; | ||
Stage #1: 2-Methylcyclohexanone With sodium hydride In toluene at 100℃; for 2h; Stage #2: methyl iodide In toluene at 60℃; for 4h; Further stages.; | ||
Stage #1: 2-Methylcyclohexanone With potassium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With triethyl borane In tetrahydrofuran at 20℃; for 16h; Stage #3: methyl iodide In tetrahydrofuran for 8h; | 2, 2-Dimethyl-cyclohexanon (Vorprodukt für Beispiel C-26) Eine Suspension von Kaliumhydrid (5. 5 mmol) und 2- Methylcyclohexanon (5 mmol) in trockenem Tetrahydrofuran (10 ml) wird während 30 min bei Raumtemperatur gerührt. Man tropft langsam Triethylboran (6. 25 mmol) zu und rührt 16 Stunden bei Raumtemperatur. Nach Zugabe von Methyliodid wird weitere 8 Stunden gerührt, die Reaktion anschliessend mit gesättigter wässriger Ammoniumchlorid-Lösung gequencht und zweimal mit Diethylether extrahiert. Die vereinigten organischen Phasen werden über Natriumsulfat getrocknet und im Vakuum zur Trockene eingeengt und ergeben die Titelverbindung, welche ohne ohne Aufreinigung weiter umgesetzt werden kann (JACS 1985, 107, 19, 5391-5396). | |
Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere; Reflux; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 3.16667h; Inert atmosphere; | ||
Stage #1: 2-Methylcyclohexanone With sodium amide In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: methyl iodide In tetrahydrofuran at 5 - 70℃; for 1h; | 12 Example 12: 2,2-dimethylcyclohexanone synthesis Take 100mL three-necked flask, removable nitrogen three times, was added through a dropping funnel was added 42mLTHF,10.9mL2- Methyl cyclohexanone (89mmol), nitrogen, was added in portions 3.9gNaNH2 (100mmol, added six points) was stirred and heated under reflux for 2h, yellow viscous solution. Cooled to 5 ,Was slowly added 7.76mLCH3I (125mmol), the solution became white viscous loaded, heated to reflux (70 About) 1h. Filtered, washed with ether and the white residue, and the combined organic phases. The organic phase was washed with saturated NH4ClSolution, saturated NaCl, then dried with anhydrous NaSO4 rotary evaporation give crude compound 10,And then distilled under reduced pressure to give a colorless liquid 7.4258g, without further purification, direct investment next step. | |
Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | ||
Stage #1: 2-Methylcyclohexanone With sodium hydride In toluene; mineral oil at 100℃; for 2h; Stage #2: methyl iodide In toluene; mineral oil at 60℃; for 2h; | 1 Step 1. To a stirred suspension of NaH (5.12 g, 134 mmol of 60% mineral oil dispersion) in dry toluene (180 mL) was added 2-methylcyclohexan-1-one (10.00 g, 89.2 mol) dropwise during 2 h at 100 °C. To this was added CH3I (19.00 g, 134 mol) dropwise over 2 h at 60 °C. The mixture was stirred for an additional 2 h at 60 °C. After cooling, a mixture of NaOMe (10.60 g, 196 mmol) and HCO2Me (11.2 g, 152 mmol) were added to the mixture at 5°C, and the reaction mixture stirred for 12 h at room temperature before being poured into ice water (100 mL). The aqueous layer was acidified with 10% HCl aqueous and extracted with ether. The combined organic phases were washed with brine, dried over MgSO4 and concentrated to afford (E)-6-(hydroxymethylene)-2,2- dimethylcyclohexan-1-one (9.00 g, 65%) as a brown oil. LCMS: LC retention time 2.09 min. MS (ESI) m/z 155 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With bis-trimethylsilanyl peroxide; 4 A molecular sieve; tin(IV) chloride; rac-diaminocyclohexane In tetrahydrofuran; dichloromethane for 2h; Ambient temperature; Yields of byproduct given; | |
1: 73% 2: 8% | With dihydrogen peroxide; trityl tetrakis(pentafluorophenyl)borate In water; 1,2-dichloro-ethane at 70℃; for 1.5h; | 24 In Examples 24 to 30, as shown in Chem. 1, lactones were synthesized from various cyclic ketones by a Baeyer-Villiger oxidation reaction using hydrogen peroxide. In Example 24, when 2-methylcyclohexanone, which was an asymmetric cyclic ketone, was used, a corresponding ε-caprolactone was obtained at a high yield with normal regioselectivity. In Example 25, when 4-isopropenylcyclohexanone, which was a cyclic ketone having a substituent with an olefinic bond, was used, a corresponding ε-caprolactone was obtained at a yield of 56%, and no epoxidation of the olefin was observed. In Example 26, when 4-hydroxycyclohexanone was used, a five-membered lactone having a hydroxyethyl group was obtained. In this case, it is construed that after a corresponding ε-caprolactone was formed, this lactone was obtained by rearrangement therefrom into a five-membered ring having a smaller ring strain. In Examples 27 to 29, when a five-membered ring ketone and a four-membered ring ketone were used, corresponding six-membered ring lactone and five-membered ring lactone were obtained at a high yield. In Example 30, when a condensed ring ketone having an olefinic bond inside the ring was used, a corresponding condensed ring lactone was obtained at a high yield with normal regioselectivity, and no epoxidation of the olefin was observed.In addition, commercially available products were used for 2-methylcyclohexanone of Example 24 and cyclopentanone of Example 27, and starting raw materials of the other Examples were synthesized in accordance with the methods described in the literatures (*1 to 5 shown in Chem. 1). |
1: 71% 2: 8% | With calcium tetrakis(pentafluorophenyl)borate undecahydrate; dihydrogen peroxide; oxalic acid In 1,2-dichloro-ethane at 70℃; for 4h; regioselective reaction; |
1: 66% 2: 34% | With bis-trimethylsilanyl peroxide; 1-hexyl-3-methylimidazolium chloroaluminate(III) at 0 - 20℃; for 24h; Acidic conditions; Inert atmosphere; | General procedure for cyclic ketones oxidation General procedure: The ketone (1.5 mmol) and silyl peroxide (2.25 mmol for reactions with bis(silyl) peroxides and 3 mmol for reactions with t-butyl silyl peroxides) were added dropwise at 0 °C into the freshly synthesised [hmim][AlxCly] (2 mmol for reactions with bis(silyl) peroxides and 3 mmol for reactions with t-butyl silyl peroxides). Next, the solution was stirred under a nitrogen atmosphere at room temperature for 1-24 h (depending on the reaction rate). After this time, 5 ml of water was added to the post-reaction mixture, and the water phase was extracted with methylene chloride or diethyl ether (10× 5 ml). The organic layer was washed with 5 ml of water, dried over anhydrous MgSO4, filtered, concentrated in a vacuum (50 °C, 100 mbar) and purified by column chromatography (hexane:ethyl acetate (4:1)) when necessary. All products were characterised by comparison of their NMR spectra (see Supplementary data) with authentic samples [20]. |
1: 22% 2: 56% | With bis-trimethylsilanyl peroxide; tin(IV) chloride In dichloromethane at 25℃; for 4h; | |
5% | ||
With oxygen; benzaldehyde In 1,2-dichloro-ethane for 21h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | ||
With bentonite clay; magnesium monoperoxyphthalate hexahydrate In acetonitrile at 59.9℃; for 2h; Yield given. Yields of byproduct given; | ||
With magnesium monoperoxyphthalate hexahydrate In acetonitrile at 70℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | ||
With cyclohexanyl peroxycarboxylic acid In hexane at 20 - 40℃; for 3h; Yield given. Yields of byproduct given; | ||
With 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) In dichloromethane for 0.2h; Ambient temperature; Yield given; Yields of byproduct given. Title compound not separated from byproducts; | ||
With Sn-Beta-2 zeolite; dihydrogen peroxide In 1,4-dioxane at 80℃; for 4h; Title compound not separated from byproducts; | ||
With Mg0779Al0.211(OH)2(C(01)O3)10*O.60H2O; dihydrogen peroxide; benzonitrile at 70℃; for 6h; | ||
With dihydrogen peroxide In various solvent(s) at 20℃; for 5h; Title compound not separated from byproducts.; | ||
1: 93 %Chromat. 2: 1 %Chromat. | With water; difluoro[4-(trifluoromethyl)phenyl]-λ3-bromane In dichloromethane at 0℃; for 1h; Inert atmosphere; | |
With AFL210 recombinant BVMO from Aspergillus flavus NRRL3357 In methanol at 20℃; for 2h; Enzymatic reaction; chemoselective reaction; | 2.3 Biotransformations General procedure: Whole-cell biotransformations were performed in 40mL amber glass vials using 1mL reaction volumes. The biotransformation reaction mixture (BRM) consisted of 0.1g wet weight/mL in 200mM Tris-HCl (pH 8), 100mM glucose and 100mM glycerol. The reactions were initiated by the addition of substrate (10mM) dissolved in methanol. Reactions were performed at 20°C for 2h, where after the reactions were stopped and extracted using an equal volume (2 times 0.5mL) of ethyl acetate containing 2mM 1-undecanol or 2mM 3-octanol as internal standard. GC-MS analysis was carried out on a Finnigan Trace GC ultra (ThermoScientific) equipped with a FactorFour VF-5ms column (60m×0.32mm×0.25μm, Varian). Chiral separation (Table S2) was performed using either a Chiraldex G-TA or B-TA column (30m×0.25mm×0.12μm, Astec). | |
With oxygen; benzaldehyde In 1,2-dichloro-ethane at 20℃; for 9h; Overall yield = > 99 %; | 2.3 Catalytic B-V Oxidation General procedure: The catalytic oxidation of ketone was carried out in a roundbottomflask of 25 mL volume equipped with magnetic stirrer.In the typical experiment, the flask was charged withsubstrate (2 mmol), CuPcTs-Zn2Al-LDH (8.0 mg), dichloroethane(10 mL), benzaldehyde (5 mmol), naphthalene(inert internal standard, 0.3 mmol) and then the mixture wasstirred at room temperature. Dioxygen was bubbled throughthe solution (10 mL min-1). We sampled during the reactionand the products were analyzed by GC-FID and GC-MSanalysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium tris(2,6-diphenylphenoxide); lithium diisopropyl amide In tetrahydrofuran; toluene at -78℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 45% 2: 43% | With boron trifluoride diethyl etherate In chloroform | |
With bismuth oxide perchlorate In dichloromethane at 20℃; for 1h; | ||
With bismuth(lll) trifluoromethanesulfonate In dichloromethane for 0.0833333h; |
With bismuth(lll) trifluoromethanesulfonate In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.9% | With morpholine; sulfur In ethanol at 20 - 45℃; for 29h; | 6.1. Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (9) A mixture of sulfur (1.1 g, 36 mmol), 2-methylcyclohexanone (4.04 g, 36 mmol), ethyl cyanoactetate (4.07 g, 36 mmol) and EtOH (150 mL) were placed in a round bottom flask and warmed to 45 °C and treated dropwise with morpholine (3.1 g, 36 mmol) over 15 min. The mixture was stirred for 5 h at 45 °C and 24 h at room temperature. Unreacted sulfur was removed by filtration, and the filtrate was concentrated under reduced pressure to afford an orange solid. The residue was loaded on a silica gel column packed with silica gel and eluted with 10% ethyl acetate in hexane. The fractions containing the desired product (TLC) were pooled and evaporated to afford 9 (6.97 g, 80.9%) as an orange solid; mp 69.9-71 °C; Rf 0.44 (hexane/EtOAc 3:1); 1H NMR (DMSO-d6): δ 1.08-1.10 (d, 3H, J = 6.6 Hz, 4-CH3), 1.25-1.28 (t, 3H, J = 6.8 Hz, COOCH2CH3), 1.57-1.78 (m, 4H), 2.39-2.43 (m, 2H), 3.15-3.17 (m, 1H), 4.10-4.24 (q, 2H, J = 6.8 Hz, COOCH2CH3), 7.23 (s, 2H, NH2 exch). Titled compound was used directly for next step without further characterization. |
43% | With morpholine; sulfur In ethanol at 45℃; for 5h; | |
42% | With morpholine; sulfur at 20℃; for 48h; | 4.1. Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (2a) A mixture of 2-methylcyclohexanone (33.6 g, 0.3 mol), ethyl 2-cyanoacetate (33.9 g, 0.3 mol), sulfur (9.6 g, 0.3 mol) and morpholine(26.1 g, 0.3 mol) were stirred at room temperature for 48 h.The mixture was directly purified with silica chromatography (5%EtOAc in hexane) to give a pale yellow solid (30.1 g, 42%). 1H NMR(400 MHz, CDCl3) δ 4.37e4.19 (m, 2H), 3.30e3.19 (m, 1H), 2.52e2.45(m, 2H), 1.94e1.70 (m, 3H), 1.67e1.58 (m, 1H), 1.35 (t, J 7.1 Hz, 3H),1.15 (d, J 6.8 Hz, 3H). LC-MS (ESI) m/z 240.1 [M H]. |
25% | With sulfur; diethylamine In ethanol at 20 - 50℃; for 25h; | Ethyl 2-amino-4-methyl-4,5,6,7-tetrahvdrobenzothiophene-3-carboxylate To a solution of 2-methylcyclohexanone [583-60-8] (1 g, 8.83 mmol) in EtOH (4 mL) was added ethyl cyanoacetate [105-56-6] (1.10 g, 9.71 mmol), sulphur [7704-34-9] (0.31 g, 9.71 mmol) and diethylamine [109-89-7] (0.973 g, 13.24 mmol). The reaction mixture was stirred at r.t. for 18 h, followed by heating at 50 °C for 7 h and then left at r.t. overnight. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica (gradient elution with 0 - 10% EtOAc in hexane) to afford the title compound (520 mg, 25%) as a yellow solid. 6H (400 MHz, DMSO -d6) 7.23 (s, 2H), 4.27 - 4.07 (m, 2H), 3.22 - 3.10 (m, 1H), 2.47 - 2.32 (m, 2H), 1.87 - 1.62 (m, 3H), 1.61 - 1.47 (m, 1H), 1.26 (t, J 7.1 Hz, 3H), 1.09 (d, J 6.7 Hz, 3H). |
With morpholine; sulfur In ethanol at 50℃; | ||
With morpholine; sulfur In ethanol at 50℃; | ||
With morpholine; sulfur In neat (no solvent) at 75℃; for 1h; | General procedure: A mixture of cyclohexanone (0.196 g,2.0 mmol), methyl cyanoacetate (0.198 g, 2.0 mmol),elemental sulfur (0.064 g, 2.0 mmol) and morpholine (0.174g, 2.0 mmol) was heated at 75 °C for 1 h. After nearlycomplete conversion to the corresponding 2-aminothiophene, as was indicated by TLC monitoring, thereaction mixture was cooled to r.t. and the solid residue wasrecrystallized from EtOH to afford methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (6a). Then asolution of 6a (0.211 g, 1 mmol) in benzonitrile (2 mL) washeated within a flask equipped with an air-filled balloon at200 °C for 24 h in a silicone oil bath. Progress of the reactionwas monitored by TLC. After completion of the reaction, the mixture was cooled to r.t. and the excess of benzonitrile wasremoved under the reduced pressure. The crude product waspurified by column chromatography using n-hexane-EtOAc(8:1) as eluent. The solvent was evaporated under thereduced pressure and the residue was crystallized from nhexane-EtOAc (5:1) to afford the pure product 7a as paleyellow crystals. Yield: 0.188 g, 91% | |
With morpholine; sulfur In ethanol at 70℃; for 5h; | Tetrahydrobenzothiophene amino esters intermediates (3) General procedure: Respective cyclohexanones (2a-2h, 1.0 eq) were dissolved in ethanol. To this solution elemental sulfur (1.1 eq) was added. Then ethyl cyanoacetate (1.1 eq) and morpholine (1.6 eq) were added and the reaction mass was stirred for 5 h at 70 0C. Then ethanol was evaporated to get the crude which was purified over silica gel column chromatography to obtain the desired product 3a-3h respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 27% 2: 28% 3: 24% | With 2,4,6-trimethyl-pyridine; iodine; silver perchlorate In dichloromethane at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With dihydrogen peroxide In water; acetonitrile at 20℃; for 24h; | |
93% | With dihydrogen peroxide In water; acetonitrile at 20℃; for 1.66667h; | |
90% | With aminosulfonic acid; dihydrogen peroxide In water; acetonitrile at 20℃; for 0.25h; Green chemistry; | General procedure for synthesis of gem-dihyroperoxides General procedure: To a mixture of carbonyl compound (1 mmol) and SA(0.0097 g, 0.1 mmol) in MeCN (2 ml) 30 % aqueous H2O2was added (3 ml), and the mixture was stirred at room temperaturefor an appropriate time (Tables 2, 3, 4). After completionof reaction as monitored by thin-layer chromatography(TLC), the mixture was diluted with water (5 ml) and extracted with CH2Cl2 (3 × 5 ml). Aqueous layer whichcontains SA and organic layer that contains products, wasseparated, dried over anhydrous Mg2SO4, and evaporatedunder reduced pressure. The residue was purified by silicapackedcolumn chromatography (hexane-EtOAc) to affordpure gem-dihydroperoxides (Tables 2, 3, 4). Products werecharacterized on the basis of their melting points, elementalanalysis and IR, 1H NMR, and 13C NMR spectral analysisand amount of peroxide in products has been determinedby iodometric titration. |
90% | With dihydrogen peroxide In water; acetonitrile at 20℃; for 0.216667h; Green chemistry; | Synthesis of gem-dihydroperoxides; general procedure General procedure: To a solution of carbonyl compound (1 mmol) and HPA/NaY (0.01 g) in CH3CN (3 mL), 30% aqueous H2O2 (1 mL, 9.8 mmol) was added and the mixture was stirred at room temperature for an appropriate time (Tables 2-4). After completion of the reaction, as monitored by TLC, the catalyst was separated by centrifuge and the solvent was evaporated under reduced pressure. The residue was purified by silica-packed column chromatography (hexane-EtOAc) to afford pure gem-dihydroperoxides (Tables 2-4, 60-97% yields). The products were characterised on the basis of their melting points, elemental analysis and IR, 1H NMR and 13C NMR spectral analyses. Also, the amount of peroxide in the products was determined by iodometric titration. |
88% | With water; dihydrogen peroxide; rhenium(VII) oxide In acetonitrile at 20℃; for 0.5h; | |
82% | With ammonium cerium(IV) nitrate; dihydrogen peroxide In water; acetonitrile at 20℃; for 2.5h; | |
80% | With dihydrogen peroxide; iodine In acetonitrile at 20℃; for 5h; | |
80% | With dihydrogen peroxide; iodine In acetonitrile at 22℃; for 5h; | |
67% | With anthracene; oxygen; isopropyl alcohol UV-irradiation; | |
65% | With dihydrogen peroxide In 1,2-dimethoxyethane at 20℃; for 15h; | |
58% | With oxygen; 9,10-phenanthrenequinone; isopropyl alcohol for 20h; visible light irradiation; | |
28.12% | With hydrogenchloride; dihydrogen peroxide In dichloromethane; water; acetonitrile at 20℃; for 2h; | Synthesis of dihydroproxides (8a-8e) General procedure: Cyclic or alicyclicketone (6a-6e) (1 ml, 10 mmol) was taken in a mixture ofCH2Cl2/CH3CN (20 ml, 1:3 v/v) at room temperature followedby addition of 30% H2O2 (10.4 ml, 0.1 mol) andconcentrated HCl (3 ml). The resulting mixture was furtherstirred for 2 h at room temperature and then quenched withsaturated NaHCO3 and CH2Cl2. The organic layer thusobtained was separated out, and the water layer was filteredto collect the precipitate and dried to obtain the desiredproduct |
Multi-step reaction with 2 steps 1: 70 percent / hydrogen peroxide; boron trifluoride diethyl etherate / diethyl ether / 1 h / 20 °C | ||
Multi-step reaction with 3 steps 1: 71 percent / hydrogen peroxide; boron trifluoride diethyl etherate / diethyl ether / 1 h / 20 °C | ||
Multi-step reaction with 3 steps 1: 79 percent / hydrogen peroxide; boron trifluoride diethyl etherate / diethyl ether / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With iodine In methanol for 5h; Heating; | |
85% | With N-Bromosuccinimide In acetonitrile at 20℃; for 5h; | General procedure: Method A: To a stirred solution of ammonium thiocyanate (1 mmol, 0.076 g) and NBS (1 mmol, 0.178 g) in acetonitrile (10 mL) was added acetophenone (1 mmol, 0.12 g) at 0 °C and the resulting mixture was stirred at room temperature for the appropriate time (Table 1). After complete conversion as indicated by TLC, the reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (2 × 10 mL). The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting product was purified by column chromatography on silica gel (Merck, 60-120 mesh, ethyl acetate/hexane, 2:8) to afford the pure thiocyanatoketone derivative. |
78% | With iron(III) chloride In dichloromethane at 20℃; for 0.5h; |
68% | With phosphomolybdic acid; copper dichloride In 1,2-dichloro-ethane at 20℃; for 0.583333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: 2.) DDQ / 1.) chlorobenzene, heating; 2.) chlorobenzene 3: potassium permanganate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 18 percent / aq. H2SO4 / 10 h / Heating 2: 41 percent / 10percent Pd on charcoal / various solvent(s) / 5.5 h / Heating | ||
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: palladium/charcoal |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; sodium methylate; sodium; iron(III) chloride In diethyl ether; water | B.i i. i. 2,2-Dimethylcyclohexanone To a suspension of 13.5 g. (0.25 mole) sodium methoxide in 500 ml. of ethyl ether was added 30.8 g. (0.28 mole) 2-methylcyclohexanone and 20.3 g. (0.28 mole) ethyl formate. The mixture was stirred at room temperature for 12 hours, filtered under a nitrogen atmosphere, the solids washed with ethyl ether and dried in the vacuum oven at 75° C. The dried cake was ground in a mortar and pestle to a fine powder to obtain 17.5 g. (43%) of sodium 2-formyl-6-methylcyclohexanone which was used in the next step. The above product, 17.5 g. (0.11 mole) was added to a mixture of 2.88 g. (0.13 mole) sodium shot, 500 ml. anhydrous ammonia and about 0.1 g. ferric chloride. The resulting gray suspension was cooled to -45° C. and stirred for one hour at the reflux temperature of the system. To this was added 20.86 g. (0.15 mole) methyl iodide, the mixture stirred three hours at reflux and allowed to evaporate while warming to room temperature overnight. The residue was suspended in 300 ml. ethyl ether, refluxed to expell traces of ammonia and water added to dissolve the solids. The ether was extracted with water (3*100 ml.), the combined aqueous layers treated with 6 g. of solid sodium hydroxide and heated to steam distill the ketone. The steam distillate was extracted with ethyl ether, the extracts washed with brine, dried and ether evaporated to provide 2,2-dimethylcyclohexanone as a colorless liquid, 2.0 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: trans-3-phenylprop-2-enyl chloride With chloro-trimethyl-silane; lithium chloride; zinc In tetrahydrofuran at 25℃; for 1h; Stage #2: 2-Methylcyclohexanone In tetrahydrofuran at -78℃; for 1h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 2-(2-fluoropyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide In dichloromethane at -78 - 0℃; for 4h; Inert atmosphere; | |
95% | With (E)-(4,4-bis((trifluoromethyl)sulfonyl)but-1-enyl)benzene In dichloromethane at 0℃; for 3h; | 15 Mukaiyama aldol reaction of 2-methylcyclohexanone using (E) - (4,4-bis (trifluoromethylsulfonyl) but-1-enyl) benzene as an acid catalyst After dissolving 110.9 mg of 2-methylcyclohexanone in 1.5 ml of dichloromethane, 19.1 mg of (E) - (4,4-bis (trifluoromethylsulfonyl) but-1-enyl) benzene was added at 0 ° C. . Subsequently, a solution of 303.0 mg of tert-butyl (1-ethoxyvinyloxy) dimethylsilane in 0.5 ml of dichloromethane was added at 0 ° C. over 1 hour using a syringe pump. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with a developing solvent of hexane / ethyl acetate = 50: 1 to give the desired ethyl 2-((1S*,2S*)-1-(tert-butyldimethylsiloxy)-2-methylcyclohexyl)acetate 293.8 mg was obtained in a yield of 95%. |
94% | With 1,1,3,3-tetrakis(perfluoromethylsulfonyl)propane In dichloromethane at -78℃; for 2.5h; Inert atmosphere; diastereoselective reaction; |
85% | With C16H21F6NO4S2 In dichloromethane at 20℃; for 0.5h; Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In dodecane at 225℃; Autoclave; | 34 Examples 34-37 were carried out in a single step using the method described in method B above. Example 34 was carried out using a mixture of the B38 zeolite with commercial nickel/alumina catalyst as described in Example 21. Examples 35-37 were carried out using a precious metal supported on the B38 solid acid, made as described in A above. These examples show that using the catalyst comprising metal on B38 or a metal catalyst mixed with B38, the amount of unidentified heavy by-product is considerably greater than that obtained using the two-stage method of Examples 30-32 in which the hydrogenation is carried out with Pd at 225° C. and then the deoxygenation over the solid acid catalyst is carried out at a lower temperature. These examples demonstrate that the presence of the solid acid deoxygenation catalyst during hydrogenation reaction is less desirable when the hydrogenation is carried out at relatively high temperature. Example 34 appears to produce significantly more methylcyclohexanone than Example 33 using the same materials. Methylcyclohexanone is an intermediate hydrogenation product and it is likely that it would have been converted to methylcyclohexanol and then deoxygenated if the reaction had been continued. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With titanium(IV) tetrabutoxide; triethylsilyl chloride In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With iodine; oxygen; toluene-4-sulfonamide In dimethyl sulfoxide at 70℃; for 24h; Green chemistry; | 1 Example 1: Will 49.0 mg (0.5 mmol) 2-methyl-cyclohexane-1-one, 2 ml dimethyl sulfoxide, 38.1 mg (0.5 mmol) thiourea, 38.1 mg (0.15 mmol) iodine, 475.6 mg (2.5 mmol) The p-toluenesulfonamide was placed in the reactor in turn and the reaction was in air and refluxed at 70 oC for 24 h. After the reaction was completed, 20 ml of water was added to the system and the mixture was extracted 3 times with 20 ml of ethyl acetate. The organic phase was collected and combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the target product after column chromatography. Yield: 84%. |
71% | With iodine; oxygen; toluene-4-sulfonic acid In dimethyl sulfoxide at 75℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With ammonium acetate; In ethanol; at 65℃; for 2h;Microwave irradiation; | General procedure: To a solution of the dinitropyridone 1 (50 mg, 0.25 mmol) in EtOH (5 mL), cyclohexanone 4a (26 muL, 0.25 mmol) and NH4OAc (289 mg, 3.75 mmol) were added, and the resultant mixture was heated at 65 C on an oil bath for 24 h. After removal of the solvent, the residue was washed with benzene (3 × 10 mL) to afford 5,6,7,8-tetrahydro-3-nitroquinoline (5a; 42 mg, 0.24 mmol, 95%) as a yellow powder. The reactions of dinitropyridone 1 with other ketones 4b-g were performed in a similar way. When the reaction was conducted using microwave heating, the procedure was analogous. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine In neat (no solvent) at 75℃; for 1h; | General Procedure for the Preparation of Alkyl 2-Aminobenzo[b]thiophene-3-carboxylates 7a-j. General procedure: A mixture of cyclohexanone (0.196 g,2.0 mmol), methyl cyanoacetate (0.198 g, 2.0 mmol),elemental sulfur (0.064 g, 2.0 mmol) and morpholine (0.174g, 2.0 mmol) was heated at 75 °C for 1 h. After nearlycomplete conversion to the corresponding 2-aminothiophene, as was indicated by TLC monitoring, thereaction mixture was cooled to r.t. and the solid residue was recrystallized from EtOH to afford methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (6a). Then asolution of 6a (0.211 g, 1 mmol) in benzonitrile (2 mL) was heated within a flask equipped with an air-filled balloon at 200 °C for 24 h in a silicone oil bath. Progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to r.t. and the excess of benzonitrile was removed under the reduced pressure. The crude product was purified by column chromatography using n-hexane-EtOAc(8:1) as eluent. The solvent was evaporated under the reduced pressure and the residue was crystallized from nhexane-EtOAc (5:1) to afford the pure product 7a as paleyellow crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a suspension of <strong>[273-70-1]thiazolo[5,4-c]pyridine</strong> (1.20 g, 8.82 mmol) in diethyl ether (100 mL) at -78 C, was added drop- wise, w-butyllithium (2.5 N in hexanes, 4.24 mL, 10.6 mmol) and the reaction mixture was aged at -78C for 30 minutes. A solution of 2-methylcyclohexanone (1.28 mL, 10.6 mmol) in diethyl ether (10.0 mL) was then added drop-wise and the reaction mixture was stirred at -78C for a further 60 minutes, before warming to room temperature over 60 minutes. The resultant mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc (x3). The combined organic extracts were dried (Na2S04) and concentrated under vacuum. The crude residue was purified by flash column chromatography (0-5% MeOH in DCM) and then C18 reverse phase column chromatography [10-70% MeOH (0.1% NH3) in H20 (0.1% NH3)] to afford a mixture of the title compounds as a white solid (0.82 g, 37% yield). LCMS (Method B): RT = 2.09, 2.19 min, m/z: 249 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,3-bis((R)-1-(naphthalen-1-yl)ethyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate; potassium <i>tert</i>-butylate; lithium tert-butoxide In hexane; pentan-1-ol at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol; at 60℃; for 4h;Inert atmosphere; | 2.00 g (0.01 mol) of <strong>[2243-56-3]1-naphthyl hydrazine hydrochloride</strong>, 1.07 g (0.01 mol) of 2-methyl cyclohexanone and 36 g of 1-butanol as a solvent were charged in a 50 mL four-necked flask, min), and under nitrogen flow (5 mL / min), reacted at 60 C for 4 hours while stirring using a magnetic stirrer to obtain a pyrrole ring-containing compound. After completion of the reaction, the solution containing the pyrrole ring-containing compound was cooled to room temperature and filtered, and then the obtained filtrate was transferred to a 200 mL four-necked flask. 0.55 g (0.005 mol) of squaric acid and 36 g of toluene were added thereto, and the mixture was stirred using a magnetic stirrer under a nitrogen flow (5 mL / min), and while removing the water eluted using the Dean Stark apparatus, the reaction was carried out under reflux conditions for 6 hours. After completion of the reaction, the obtained reaction solution was concentrated with an evaporator, and the obtained solid was purified by column chromatography (developing solvent: chloroform), and the purified isolate was further recrystallized in methanol, to obtain 0.4 g of Comparative Squarylium Compound 1 shown in Table 1. The yield based on squaric acid was 23.1 mol%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.6% | With acetic acid; for 2h;Inert atmosphere; Reflux; | into a 100 mL four-necked flask,2.27 g (0.01 mol) of the intermediate G1 obtained above,1.12 g (0.01 mol) of 2-methylcyclohexanone,50 g of acetic acid was charged as a solvent, and under nitrogen flow (5 mL / min)While stirring using a magnetic stirrer,The reaction was carried out under reflux conditions for 2 hours. After completion of the reaction,The reaction solution, 200 mL of ethyl acetate and 300 mL of water were added to a separating funnel, and the organic phase was extracted vigorously with stirring,Magnesium sulfate (anhydrous) was added to the extracted organic phase and dehydrated.After removing the solid matter (inorganic component) from this organic phase,The solvent was distilled off using an evaporator. After distilling off the solvent,Dried at 60 C. for 12 hours using a vacuum dryer,4a-methyl-6- (methylsulfonyl) -2,3,4,4a-tetrahydro-1 H-carbazole (Intermediate G2). The yield based on the intermediate G1 wasIt was 80.6 mol%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum (III) chloride; oxygen; Rose Bengal lactone In acetonitrile at 20℃; for 48h; Irradiation; Overall yield = 59 %; Overall yield = 51.7 mg; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With morpholine; sulfur at 20℃; for 48h; | 4.1. Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (2a) General procedure: A mixture of 2-methylcyclohexanone (33.6 g, 0.3 mol), ethyl 2-cyanoacetate (33.9 g, 0.3 mol), sulfur (9.6 g, 0.3 mol) and morpholine(26.1 g, 0.3 mol) were stirred at room temperature for 48 h.The mixture was directly purified with silica chromatography (5%EtOAc in hexane) to give a pale yellow solid (30.1 g, 42%). |
[ 23735-46-8 ]
1-(Bicyclo[2.2.2]octan-2-yl)ethanone
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[ 14073-97-3 ]
(2S,5R)-2-Isopropyl-5-methylcyclohexanone
Similarity: 1.00
[ 23735-46-8 ]
1-(Bicyclo[2.2.2]octan-2-yl)ethanone
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[ 14073-97-3 ]
(2S,5R)-2-Isopropyl-5-methylcyclohexanone
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