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CAS No. : | 17496-14-9 | MDL No. : | MFCD00192303 |
Formula : | C10H10O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BEKNOGMQVKBMQN-UHFFFAOYSA-N |
M.W : | 146.19 | Pubchem ID : | 249262 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.3 |
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) : | -5.6 cm/s |
Log Po/w (iLOGP) : | 1.93 |
Log Po/w (XLOGP3) : | 2.24 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 2.01 |
Log Po/w (SILICOS-IT) : | 2.83 |
Consensus Log Po/w : | 2.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.56 |
Solubility : | 0.402 mg/ml ; 0.00275 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.23 |
Solubility : | 0.853 mg/ml ; 0.00583 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.25 |
Solubility : | 0.0822 mg/ml ; 0.000562 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.89 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium tetrahydroborate In toluene | EXAMPLE G 2-Methylindene (6) Analogously to Example D, 5.0 g (34 mmol) of 2-methyl-1-indanone (5) were reduced with 1.94 g (51 mmol) of NaBH4. The alcohol, which was not purified further, was then further reacted in the presence of 0.2 g of p-toluene-sulfonic acid in 100 ml of toluene at 80° C. Chromatography on 100 g of silica gel (hexane/methylene chloride 9:1) gave 3.68 g (82percent) of 2-methylindene (6). 1 H-NMR spectrum (100 MHz, CDCl3): 7.2 (4,m), 6.45 (1,m), 3.25 (2,m), 2.1 (3,m). Mass spectrum: 130 M+, correct disintegration pattern. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With MeMgBr; toluene-4-sulfonic acid; hydroquinone In toluene | Part 1 2-methylindene To an ether solution of MeMgBr (260 ml, 3M) diluted with ether (300 ml) and cooled to 03 C., 2-methylindanone (99.16 g) was added dropwise as an ether solution over 2.5 hours. After stirring 2.0 hours, the reaction mixture was hydrolyzed with aqueous HCl. The water phase was separated and extracted twice with ether (300 ml). The combined organic phases were dried over sodium sulfate. Evaporation of the solvent gave a crude brown product (107 g) which was distilled under reduced pressure to give 2-methyl-2-indanol (66.2 g) as a white crystalline solid. 2-Methyl-2-indanol (66.2 g) was dissolved in toluene (500 ml) in a 1 liter flask equipped with a Dean-Stark trap. To this solution p-toluene sulfonic acid (2 g) and a small amount of hydroquinone were added, and the mixture was refluxed for 2.5 hours. After 8 ml of H2 O was generated, the reaction mixture was cooled to 0° C. and H2 O (1 liter), also cooled to 03 C., was added. The organic phase was separated and washed three times with water (500 ml). The toluene was evaporated and the residue (with trace of hydroquinone added) was distilled at reduced pressure to give 2-methylindene (47.2 g, 48percent) as clear slightly green liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrogenchloride; amalgamated zinc for 18h; Heating; | |
With hydrogenchloride; amalgamated zinc | ||
With hydrogen |
With amalgamated zinc | ||
Multi-step reaction with 3 steps 1: NaBH4 / tetrahydrofuran; methanol / 4 h / 25 °C 2: p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 3: 95 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 - 1551.4 Torr | ||
Multi-step reaction with 2 steps 1: sodium; alcohol 2: fuming hydriodic acid / 210 °C / im Rohr | ||
With hydrogenchloride In ethanol | 8.d 2-methyl-5-indanacetic acid (d) A solution of 28.7 g of 2-methyl-1-indanone in 500 cc of ethanol is hydrogenated for 4 hours at room temperature under pressure with the addition of 2.5 g of palladium charcoal (10%) and 20 cc of concentrated hydrochloric acid. The solution is concentrated to approximately 100 cc, is diluted with water and extracted with petroleum ether. The extract is washed with water, dried over sodium sulphate and concentrated by evaporation. The resulting 2-methyl-indan is purified by chromatography on 200 g of aluminum oxide with petroleum ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux; | |
81% | With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 60℃; for 1.5h; Heating / reflux; | A3.a Example A3; 2-Amino-4-[(1R,2S)-2-methyl-1-indanylamino]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine (Table 2, Compound number 2.1); a. 2-methyl-indan-1-one oxime a. 2-methyl-indan-1-one oxime A mixture of 2-methyl-1-indanone (10 g, 0.0684 mol) and hydroxylamine hydrochloride (9.5 g, 0.1368 mol) in ethanol was stirred at 60° C., and a solution of sodium acetate (16.8 g, 0.2052 mol) in water added.The resulting mixture was then heated at reflux for 90 minutes, then cooled and the solid filtered.The crude product was washed with water and filtered to give 2-methyl-indan-1-one oxime (9.9 g, yield 81%), mp. 82-91° C., in 90% purity. |
With methanol; hydroxylamine hydrochloride; potassium carbonate oxime of/the/ <i>dl</i>-form; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With methanol; sodium tetrahydroborate In tetrahydrofuran at 20℃; Cooling; | |
With ethanol; sodium | ||
With sodium tetrahydroborate |
With sodium tetrahydroborate In tetrahydrofuran; methanol at 25℃; for 4h; | ||
With sodium tetrahydroborate In isopropyl alcohol at 25℃; for 2h; | ||
With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; | ||
With sodium tetrahydroborate In methanol at 20℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine at 100℃; | ||
With chloroform; bromine | ||
With tetrachloromethane; bromine |
With bromine In tetrachloromethane | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 90 °C 2: copper(ll) bromide / acetonitrile / Reflux | ||
With bromine; acetic acid In dichloromethane at 20℃; for 12h; | ||
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With PPA | |
83% | With terbium(III) trifluoromethanesulfonate In chlorobenzene at 250℃; for 8h; | |
83% | With polyphosphoric acid at 80℃; for 12h; | 5.1.6 General procedure C: the synthesis of indenone from propanoic acid derivative by F-C acylation General procedure: A mixture of the crude propanoic acid derivative (42.0 mmol, 1.0 equiv) and polyphosphoric acid (400 mmol, 9.5 equiv) was stirred at 80 °C for 12 h. The resulting mixture was poured into ice water and extracted with EtOAc (30 mL × 3). The combined extracts were washed with a saturated aqueous NaHCO3 (10 mL × 3) to remove the starting acids, and then washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography to afford indenone |
74% | With polyphosphoric acid at 80℃; for 4h; | |
With sulfuric acid <i>dl</i>-β-methyl-hydrindone; | ||
With sulfuric acid at 100℃; | ||
(i) PCl5, PE, (ii) AlCl3; Multistep reaction; | ||
Multi-step reaction with 2 steps 1: 100 percent / SOCl2 / 3 h / 80 °C 2: 89 percent / AlCl3 / benzene / 1.5 h / Heating | ||
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1 h / 35 - 40 °C 2: aluminum (III) chloride / dichloromethane / 3 h / 0 - 10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With oxygen; copper(l) chloride; 2-hydroxy-4,5,6,7-tetraphenylisoindoline-1,3-dione In acetonitrile at 35℃; for 27h; atmospheric pressure; | |
With sodium acetate; acetic acid (electrolysis); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; | To a solution of 176 g (1.21 mol) of 2-methylindan-1 -one and 205 g (1.44 mol, 1.2 eq.) of Mel in 200 ml of THF cooled to0°C., a solution of 176 g (1.57 mol, 1.3 eq.) ofl3uOK in 1200 ml of THF was added dropwise for 4 h. The reaction mixture was stirred overnight at room temperature and then poured into 2 liters ofwatet Crude product was extracted with 300 ml of hexane and then 2x300 ml of dichloromethane. The combined organic extract was dried over K2C03, passed through a short pad of silica gel 60 (40-63 um), and the eluent was evaporated to dryness to give red oil. This oil was then distilled in vacuum to give 185 g (96%) of 2,2-dimethylindan- 1-one as yellowish oil which crystallizes at room temperature, b.p. 76-78° C/S mm Hg.10351] Anal. calc. for C,,H,20: C, 82.46; H, 7.55. Found:C, 82.24; H, 7.61.j0352] ‘H NMR (CDC13): ö 7.76 (d, 1H, J=7.6 Hz), 7.59 (dt, 1H, J=7.6, 1.2 Hz), 7.44-7.35 (m, 2H), 3.00 (s, 2H), 1.24 (s, 6H). ‘3C{’H} NMR (CDC13): ö 211.38, 152.18, 135.30, 134.77, 127.37, 126.59, 124.40, 45.43, 42.81, 25.22. |
With potassium <i>tert</i>-butylate | ||
With n-butyllithium 1.) THF; Yield given. Multistep reaction; |
Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With sodium tert-pentoxide In tetrahydrofuran at 20℃; for 0.25h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With hydrogenchloride In ethanol for 2h; Heating; | |
39% | With hydrogenchloride In ethanol | 50 cis-9b,10-Dihydro-8,9b-dimethylindeno[1,2-b]indole EXAMPLE 50 cis-9b,10-Dihydro-8,9b-dimethylindeno[1,2-b]indole To a solution of 4-methylphenylhydrazine hydrochloride, (9.73 g, 0.06 mmol) in a absolute ethanol (240 cm3) was added dropwise 2-methyl-1-indanone, (8.14 g, 0.056 mmol), followed by conc. hydrochloric acid (3 cm3). The mixture was boiled for 2 hours, the solvents removed, and the residue portioned between diethyl ether and water, and the layers separated. The aqueous phase was extracted with diethyl ether (3*50 cm3). The combined organic phases were washed sequentially with saturated sodium bicarbonate solution and brine, dried (Na2 SO4), and evaporated. The crude material thus obtained was purified by flash chromatography on silica gel, eluding with 7-12% ethyl acetate/60°-80° petrol to yield a solid (5.05 g, 39%) 1 H NMR (CDCl3) δ: 7.87 (1H, m) 7.51 (1H, d, J=7.9 Hz) 7.39 (3H, m) 7.25 (1H, s) 7.15 (1H, d, J=8.0 Hz) 3.07 (1H, d, J=14.7 Hz) 2.81 (1H, d, J=14.7 Hz) 2.41 (3H, s) 7.37 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; In water; toluene; | Preparation of 2-methylindene: Diisobutylaluminium hydride (6 g, 42 mmoles) was added dropwise to 2-methyl-1-indanone (5.0 g, 34 mmoles) dissolved in 50 ml of anhydrous toluene, while the reaction temperature was kept at room temperature. The reaction mixture was stirred for 0.5 h after the addition. The reaction mixture was hydrolyzed by being added dropwise to sulfuric acid (aqueous 25 wt %, 50 ml) at 70 C. After the addition the aqueous layer was discarded, and the organic layer was washed twice with sulfuric acid (aqueous 5 wt %, 50 ml) and once with water (50 ml). p-Toluenesulfonic acid (50 mg) was added to the organic layer, and the reaction mixture was heated under reflux with water separation for 1 h. After cooling to room temperature the organic layer was washed with sodium bicarbonate (aqueous 2 wt %, 50 ml), dried over magnesium sulfate, and carefully concentrated under reduced pressure. The yield of 2-methylindene was 4.2 g or 94%. 1H-NMR spectrum (400 MHz, CDCl3): 2.13 (s, 3H), 3.27 (s, 2H), 6.47 (s, 1H), 7.08 (d, 1H), 7.09-7.17 (m, 2H), 7.33 (d, 1H). | |
3.68 g (82%) | With sodium tetrahydroborate;toluene-4-sulfonic acid; In toluene; | EXAMPLE G 2-Methylindene (6) Analogously to Example D, 5.0 g (34 mmol) of 2-methyl-1-indanone (5) were reduced with 1.94 g (51 mmol) of NaBH4. The alcohol, which was not purified further, was then further reacted in the presence of 0.2 g of p-toluene-sulfonic acid in 100 ml of toluene at 80 C. Chromatography on 100 g of silica gel (hexane/methylene chloride 9:1) gave 3.68 g (82%) of 2-methylindene (6). 1 H-NMR spectrum (100 MHz, CDCl3): 7.2 (4,m), 6.45 (1,m), 3.25 (2,m), 2.1 (3,m). Mass spectrum: 130 M+, correct disintegration pattern. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; | 2-Methyl-2,3-dihydro-1H-inden-1-one (20a) To a solution of 19a (1.44 g, 10 mmol) in EtOAc (20 mL),10% Pd/C (20% weight of compound 19a) was added. The mixture was stirred overnight undera hydrogen atmosphere at room temperature. Insoluble materials were removed by filtration andwashed with EtOAc. The filtrate was evaporated to dryness under reduced pressure to give 20a (1.43 g,98%) as a colorless transparent liquid. 1H-NMR: δ 7.76 (d, J = 7.7 Hz, 1H), 7.59 (d, J = 7.6, 1H), 7.45 (d,J = 7.7 Hz, 1H), 7.37 (t, J = 7.4 Hz, 1H), 3.45-3.36 (m, 1H), 2.79-2.68 (m, 2H), 1.35-1.30 (m, 3H); ESI-MS:m/z [M + H]+ 147. |
50% | With ephedrine; hydrogen In acetonitrile at 20℃; for 0.75h; | |
With carbon monoxide In dichloromethane at 22℃; various amount of catalyst, reagent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethyl borane; potassium hydride | |
76% | Stage #1: inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran for 12h; Further stages.; | |
65% | Stage #1: inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 14h; Further stages.; |
61% | Stage #1: inden-1-one With lithium hexamethyldisilazane In tetrahydrofuran at -40℃; for 2h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at -40 - 20℃; Inert atmosphere; | |
32% | Stage #1: inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | |
30% | Stage #1: inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 12h; | |
With lithium diisopropyl amide 1) THF, -78 deg C, 1.5 h, 2) 4 h, -78 deg C; Yield given. Multistep reaction; | ||
With lithium hexamethyldisilazane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 0.5h; | |
81% | With azobisisobutyronitrile; tri-n-butyl-tin hydride In benzene for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.8% | With aluminum (III) chloride In dichloromethane at 0 - 10℃; for 3h; | 1.C C. 136.3 g of the organic phase obtained in step B was added to 200 g of dichloromethane, and then 148.1 g of thionyl chloride (1.24 mol) was added dropwise at 35-40 ° C. After the completion of the dropwise addition, the mixture was kept for 1 h. At the end point, the concentrated solution of the acid chloride was desolved; another reaction flask was added, 166.1 g of aluminum trichloride (1.24 mol) and 300 g of dichloromethane were respectively added, the internal temperature was lowered to 0 ° C, and then the acid chloride concentrate was added dropwise, within 3 hours. After the completion of the dropwise addition, the internal temperature was controlled at 0-10 ° C, and the GC control showed that the end point was reached. 200 g of 5% aqueous HCl solution was added dropwise to quench the reaction, and the mixture was allowed to stand for separation. The separated organic layer was desolvated and rectified to obtain a pale yellow color. Liquid 117.9g, GC purity 98.7%, yield 95.8% |
89% | With aluminium trichloride In benzene for 1.5h; Heating; | |
With aluminium trichloride In tetrachloromethane |
2.64 g | With aluminum (III) chloride In toluene for 1.5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With toluene-4-sulfonic acid at 90℃; | 1 General procedure for acetylation of ketones/aldehydes General procedure: For a typical 10.0 mmol scale reaction, the starting material was dissolved in isopropenyl acetate (2.2mL, 20 mmol, 2 equiv) and para-toluene sulfonic acid (0.20 g, 1 mmol, 10 mol%) was added. The resulting mixture was stirred at 90°C until full conversion was achieved (TLC). Saturated aqueous NaHCO3 (15mL) and Et2O (20mL) were added and the products were extracted using further Et2O (2×20 mL). After drying over Na2SO4 and concentration in vacuo, crude products were purified using SiO2 column chromatography (hexane/EtOAc) where necessary. |
With toluene-4-sulfonic acid Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With palladium; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium hexamethyldisilazane In tetrahydrofuran at -78 - -20℃; Stage #2: With N-fluorosultam In tetrahydrofuran | |
77% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: With 2-fluoro-2H-1λ6-benzo[e][1,2]thiazine 1,1-dioxide In tetrahydrofuran at -40℃; | |
72% | With toluene-4-sulfonic acid; Selectfluor In dichloromethane; acetonitrile at 25℃; for 40h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | |
91% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; Further stages.; | |
79% | With lithium diisopropyl amide In tetrahydrofuran cooling; |
70% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran for 3h; Further stages.; | |
Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium diisopropyl amide In tetrahydrofuran Stage #2: chloro-trimethyl-silane With triethylamine | ||
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃; | ||
Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78℃; for 1h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexanes at -78 - 20℃; | ||
Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With sodium iodide In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: chloro-trimethyl-silane With triethylamine In acetonitrile at 20℃; Inert atmosphere; | ||
With triethylamine; sodium iodide In acetonitrile at 0 - 23℃; for 16h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; Stage #2: Nitrosobenzene In tetrahydrofuran at -78℃; for 0.0833333h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 80% 2: 4% | With tetraethylammonium tosylate In N,N-dimethyl-formamide at 60℃; Electrolysis; | |
1: 46% 2: 11% | With 1,4,8,11-tetraazacyclotetradecane based Ni(II); tetraethylammonium tosylate; diphenylphosphane In N,N-dimethyl-formamide at 60℃; Electrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: diethyl chlorophosphate In tetrahydrofuran at -78 - 20℃; | |
87% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium diisopropyl amide at -78℃; Stage #2: diethyl chlorophosphate at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: chlorotriethoxysilane In tetrahydrofuran; hexane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With oxygen; caesium carbonate; triethyl phosphite In dimethyl sulfoxide at 25℃; for 24h; Schlenk technique; | |
94.1% | With oxygen; sodium hydroxide; sodium sulfite In ethanol at 15℃; for 6h; | 20 Example 20 Synthesis of 2-hydroxy-2-methyl-2,3-dihydro-1-indanone At 15 ° C,To a 250 ml three-necked flask was added sodium hydroxide (8 g, 0.2 mol) and ethanol (150 ml)Stir0.5h.Followed by the addition of sodium sulfite(25.21 g, 0.2 mol), 2-methyl-2,3-dihydro-1-indanone (29.24 g, 0.2 mol) followed by a 1000 ml size oxygen ball and stirred for 6 h.After completion of the reaction, the pH of the reaction solution was adjusted to 7 with 2M hydrochloric acid, and ethanol was distilled off under reduced pressure. Add 50 ml of water to(30 ml x 3), the combined organic phase was dried over anhydrous Na2SO4, and the mixture was partitioned with toluene. The solvent was evaporated to dryness to give 31.15 g of a pale yellow solid, 98% purity and 94.10% yield. |
88% | With 10% Pd on charcoal; oxygen; triethylamine In ethanol at 20℃; for 38h; |
88% | With Pd2hpp4; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen In tetrahydrofuran at 6℃; for 12h; regioselective reaction; | |
88% | With triphenylphosphine hydrobromide; dimethyl sulfoxide at 50℃; for 48h; Inert atmosphere; chemoselective reaction; | |
79% | With lithium hydroxide; oxygen; triethyl phosphite In ethanol at 80℃; for 13h; | |
74% | With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; dimethyl sulfoxide at 25℃; for 24h; Schlenk technique; | |
67% | With N-Bromosuccinimide; dimethyl sulfoxide at 80℃; for 24h; | |
67% | With N-Bromosuccinimide; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; | 35 Embodiment 352 - hydroxy -2 - methyl - 2, 3 - dihydro -1 - indenone preparation Taking a 25 ml Schlenk reaction tube, adding N - bromo succimide (NBS) 18 mg (0.1mmol) as catalyst, 2 - methyl - 2, 3 - dihydro -1 - indenone 74 mg (0.5mmol), dimethyl sulfoxide (DMSO) 1 ml as the oxidizing agent, carbonylating and solvent, for 80 °C stirring for 24 hours. After the reaction by adding ethyl acetate 15 ml, salt water 3 ml, ethyl acetate 3 times, the combined organic phase, column chromatography separation to obtain 2 - hydroxy -2 - methyl - 2, 3 - dihydro -1 - indenone pure product 54 mg, yield 67%. |
64% | With Nitrosobenzene; trichloroacetic acid In toluene at 20℃; Inert atmosphere; | Exemplary Procedure In a GC vial 2-phenylcyclohexanone (1a, 43.6 mg, 0.25 mmol,1.0 equiv) was dissolved in a solution of trichloroacetic acid(0.75 mmol, 3.0 equiv) in dry PhMe (2.5 mL) and nitrosobenzene(0.625 mmol, 2.5 equiv) was added. The vial was closedwith a screw cap, and the resulting mixture was stirred at r.t. for16 h. The crude reaction mixture was directly purified by flashcolumn chromatography (SiO2, hexanes/EtOAc = 100:0 then10:1) to give 2-hydroxy-2-phenylcyclohexan-1-one (2a) as anorange oil (28.7 mg, 60%). |
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran / 1 h / -78 °C 1.2: 87 percent / tetrahydrofuran / -78 - 20 °C 2.1: m-chloroperbenzoic acid / CH2Cl2 / -20 °C 3.1: 65 percent / trifluoroacetic acid / diethyl ether; H2O / 5 °C | ||
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: Et3N 2.1: O2 / [Cu(bpy)(BF4)2(H2O)2(bpy)]n / ethanol; H2O / 5 h / 0 °C / 760 Torr 2.2: 68 percent / triethyl phosphite / ethanol; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium hexamethyldisilazane In toluene at 20℃; for 0.0833333h; Stage #2: 2-bromo-3,3,3-trifluoropropene In toluene at 80℃; for 24h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium hexamethyldisilazane In toluene at 20℃; for 0.0833333h; Stage #2: cyclohex-1-en-1-yl trifluoromethane sulfonate In toluene at 80℃; for 24h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium hexamethyldisilazane In toluene at 20℃; for 0.0833333h; Stage #2: 2-[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-enecarboxylic acid methyl ester In toluene at 80℃; for 24h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium hexamethyldisilazane In toluene at 20℃; for 0.0833333h; Stage #2: 2-bromoprop-1-ene In toluene at 80℃; for 24h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With potassium <i>tert</i>-butylate In tetrahydrofuran at -78℃; for 0.5h; Stage #2: cyclohex-2-en-1-yl 1H-imidazole-1-carboxylate With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With C46H52N4O2(2+)*2Br(1-); oxygen; sodium hydroxide; triethyl phosphite In water; benzene at 23℃; for 18h; enantioselective reaction; | |
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran / 1 h / -78 °C 1.2: 68 percent / tetrahydrofuran / -78 - 20 °C 2.1: NaOCl; phosphate buffer; 4-phenylpyridine N-oxide / (salen) Mn(III) Jacobsen's catalyst / CH2Cl2 / 18 h / -10 - 0 °C / pH 11 2.2: trifluoroacetic acid / diethyl ether; H2O / 0 °C | ||
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 - 20 °C / Inert atmosphere 2.1: potassium hexacyanoferrate (III); potassium carbonate; osmium(VIII) oxide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; methanesulfonamide / <i>tert</i>-butyl alcohol; water / 20 h / 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In N,N-dimethyl-formamide; toluene Irradiation; | |
Multi-step reaction with 2 steps 1.1: diethyl cyanophosphonate / dimethylformamide / 0.5 h / 0 °C 1.2: 39 percent / Et3N / dimethylformamide / 2 h / 0 °C 2.1: 4 percent / tetraethylammonium tosylate / dimethylformamide / 60 °C / Electrolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With n-butyllithium In tetrahydrofuran | 9 9.1 Preparation of 1-(8-quinolyl)-2-methylindene EXAMPLE 9 9.1 Preparation of 1-(8-quinolyl)-2-methylindene 6.70 ml of n-BuLi (16.8 mmol) were added dropwise at 100° C. to 3.50 g of o-bromoquinoline (16.8 mmol) dissolved in 50 ml of THF, and the mixture was subsequently stirred at 80° C. for 15 minutes. A solution of 50 ml of THF and 2.45 g of 2-methyl-1-indanone (16.8 mmol) was then added to the lithiated bromoquinoline over the course of 10 minutes. The mixture was allowed to cool to room temperature, and the solution was then refluxed for three hours, cooled to room temperature, acidified to pH 1 using ice and hydrochloric acid and subsequently refluxed for three hours. The reaction mixture was adjusted to pH 9 using ammonia solution, and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried, and the solvent was removed. The crude product was purified by distillation under reduced pressure at 150-160° C./10-2 mbar, giving 1.5 g of 1-(8-quinolyl)-2-methylindene (45%) as a yellow, viscous resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; methyllithium; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; ethanol; hexane; ethyl acetate; | EXAMPLE 15 cis-4b,5,9b,10-Tetrahydro-4b,6,8,9b-tetramethylindeno[1,2-b]indole A mixture of 5.1 g (0.03 mol) of <strong>[60480-83-3]2,4-dimethylphenylhydrazine hydrochloride</strong>, 5,4 g (0.03 mol) of 2-methyl-1-indanon, 100 ml of ethanol (99, 5%) and 2.5 ml of conc. hydrochloric acid was refluxed for 2 hours. The resulting mixture was filtered, the filtrate was evaporated and the residue partioned between ether and water. The organic phase was washed with aqueous sodium carbonate, dried (MgSO4), filtered and evaporated. The residue was subjected to flash chromatography on 60 A silica. After elution of non-polar impurities with dichloromethane/isooctane (1/1), a mixture of methanol/ethyl acetate/hexane (1/4/5) eluted 5 g of crude 9b,10-dihydro-6,8,9b-trimethylindeno[1,2-b]indole. Without further purification this material was dissolved in 100 ml of dry tetrahydrofurane. In an argon atmosphere, 50 ml of 1.6M methyl lithium in ether was added at -65 to -55 C. The resulting mixture was kept at -78 C. for 1 hour, and was then poured into a cold aqueous ammonium chloride solution. The mixture was extracted with ether and the combined organic phases were evaporated to yield 5 g of a green oil. Chromatography on 60 A silica using 7.5% ethyl acetate in isooctane gave 1 g of the title compound. 1 H NMR (CDCl3) delta; 1.37 (3H,s), 1.48 (3H,s), 2.07 (3H,s), 2.20 (3H, s),3.00-3.35 (2H, AB-system, J 15 Hz), 3.9 (1H,bs) 6.60 (1H,s) 6.88 (1H,s), 7.08-7.28 (4H,m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With MeMgBr; toluene-4-sulfonic acid; hydroquinone; In toluene; | Part 1 2-methylindene To an ether solution of MeMgBr (260 ml, 3M) diluted with ether (300 ml) and cooled to 03 C., 2-methylindanone (99.16 g) was added dropwise as an ether solution over 2.5 hours. After stirring 2.0 hours, the reaction mixture was hydrolyzed with aqueous HCl. The water phase was separated and extracted twice with ether (300 ml). The combined organic phases were dried over sodium sulfate. Evaporation of the solvent gave a crude brown product (107 g) which was distilled under reduced pressure to give 2-methyl-2-indanol (66.2 g) as a white crystalline solid. 2-Methyl-2-indanol (66.2 g) was dissolved in toluene (500 ml) in a 1 liter flask equipped with a Dean-Stark trap. To this solution p-toluene sulfonic acid (2 g) and a small amount of hydroquinone were added, and the mixture was refluxed for 2.5 hours. After 8 ml of H2 O was generated, the reaction mixture was cooled to 0 C. and H2 O (1 liter), also cooled to 03 C., was added. The organic phase was separated and washed three times with water (500 ml). The toluene was evaporated and the residue (with trace of hydroquinone added) was distilled at reduced pressure to give 2-methylindene (47.2 g, 48%) as clear slightly green liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 46% 2: 8% | With sulfuric acid; potassium nitrate In water at -5 - 20℃; | |
1: 44% 2: 8% | With nitric acid at -10℃; for 1h; | |
1: 8% 2: 44% | With nitric acid at -10℃; for 1.16667h; | 83 2-Methyl-6-nitro-1-indanone (89). 2-Methyl-1-indanone (88) (18.74 g, 128 mmol) was added dropwise to stirred fuming HNO3 (100 mL) at -10 0C over 1 h. The mixture was stirred at -10 0C for 10 min then poured into ice/water (1 L) and the mixture stirred for 1 h. The precipitate was filtered and the filtrate extracted with DCM (4 x 80 mL). The combined organic fraction was dried and the solvent evaporated. The combined residue was purified by chromatography, eluting with a gradient (10-20%) of EtOAc/pet. ether, to give (i) 2- methyl-4-nitro-1-indanone (89) (1.89 g, 8%) as a tan solid: mp 61-63 0C [lit. Murray, R. J. & Cromwell, N. H., J. Org. Chem. 1976, 41, 3540) mp (Et2O/pet. ether) 74-75 0C]; 1H NMR δ 8.46 (dd, J = 8.0, 1.1 Hz, 1 H, H-5), 8.08 (br d, J = 7.5 Hz, 1 H, H-7), 7.60 (br dd, J = 8.0, 7.5 Hz, 1 H, H-6), 3.93 (dd, J = 19.2, 8.0 Hz, 1 H, H-3), 3.20 (dd, J = 19.2, 4.0 Hz, 1 H, H-3), 2.76-2.85 (m, 1 H, H-2), 1.37 (d, J = 7.5 Hz, 3 H, CH3); and (ii) 2-methyl-6-nitro- 1-indanone (90) (10.76 g, 44%) as a tan solid: mp 60-61 0C; 1H NMR δ 8.56 (d, J = 2.0 Hz, 1 H, H-7), 8.44 (dd, J = 8.4, 2.2 Hz, 1 H, H-5), 7.63 (d, J = 8.4 Hz, 1 H, H-4), 3.48- 3.54 (m, 1 H, H-2), 2.81-2.90 (m, 2 H1 H-3), 1.36 (d, J = 7.3 Hz, 3 H, CH3). Anal, calcd for C10H9NO3: C, 62.8; H, 4.7; N, 7.3. Found: C, 62.7; H, 4.8; N, 7.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 82 % ee 2: 39 % ee | With sodium hydroxide; hydrogen In water; toluene at 25℃; for 18h; | D3 Example D3: Hydrogenation of 2-methyl-1-indanone2-Methyl-1-indanone (racemic): 0.14 ml (1.0 mmol); catalyst: 4.90 mg (5.02 μmol) of K2; S/C: 200; base: 1.0 ml (1.0 mmol) of 1 M aqueous NaOH; solvent: toluene 3 ml; 80 bar of H2/25°C; 18 hours. 93% conversion, diastereomer ratio: 95:5; 82% or 39% ee, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate In toluene at 80℃; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate In toluene at 60℃; for 40h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate In toluene at 60℃; for 40h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate In toluene at 80℃; for 70h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate In toluene at 60℃; for 50h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate In toluene at 60℃; for 40h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: methyl cyanoformate In tetrahydrofuran at -78 - -20℃; for 0.666667h; | 1 Step 1: Methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate Preparation To a flask cooled at 0 degrees Centigrade containing diisopropylamine (2.06 mL, 14.58 mmol) in tetrahydrofuran (14 mL) was added dropwise over 15 minutes a solution of n-butyl lithium (5.55 mL of 2.5 M in hexanes, 14.58 mmol). This mixture was stirred for 30 min. A second flask containing the 2-methyl-1-indanone (2.03 g, 13.89 mmol) in tetrahydrofuran (10 mL) was cooled to -78 degrees Centigrade under N2. The freshly prepared lithium diisopropylethylamide was cooled to -78 degrees centigrade and added drop wise via cannula. The orangish mixture became somewhat heterogeneous over 30 minutes and then neat methyl cyanoformate (1.32 mL, 16.66 mmol) was added and the reaction mixture stirred an additional 40 minutes while allowing the reaction to warm to -20 degrees centigrade. The reaction was quenched with saturated aqueous NH4Cl solution and the organics extracted 2*25 mL diethyl ether, washed one time in brine, then dried (Na2SO4), filtered and concentrated to give methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate. No further purification was necessary. 1H NMR (400 MHz, CDCl3) delta ppm 1.52 (s, 3H) 3.00 (d, J=17.32 Hz, 1H) 3.67-3.73 (m, 4H) 7.41 (t, J=7.57 Hz, 1H) 7.47 (m, 1H) 7.63 (m, 1H) 7.79 (d, J=7.57 Hz, 1H) | |
Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl cyanoformate In tetrahydrofuran; hexane for 0.666667h; | III-16.1 methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate To a solution of diisopropylamine (2.06 mL, 14.6 mmol) in THF (14 mL) at 0° C. was a solution of n-butyl lithium (5.55 mL of a 2.5 M in solution in hexanes; 14.6 mmol), dropwise over 15 min. Meanwhile, a solution of 2-methyl-1-indanone (2.03 g, 13.9 mmol) in THF (10 mL) was prepared and cooled to -78° C. under N2. After 30 minutes the above solution of LDA was cooled to -78° C. and added to the above solution of indanone, dropwise over 15 min via double-ended needle. The mixture was stirred 30 min and methyl cyanoformate (1.32 mL, 16.7 mmol) was added. The mixture was stirred 40 minutes, gradually warming ca. to -20° C., quenched with satd NH4Cl and extracted with Et2O (2×25 mL). Combined organics were washed (brine), dried over Na2SO4and concentrated in vacuo, affording the title compound which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: pyrrole-1-carboxylic acid cyclohex-2-enyl ester With boron trifluoride diethyl etherate In 1,2-dimethoxyethane at -78℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With sodium hexamethyldisilazane In 1,2-dimethoxyethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 1-Pyrrolcarbonsaeure-2-propenylester With boron trifluoride diethyl etherate In 1,2-dimethoxyethane at -78℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.5h; Stage #2: 2-(3-bromopropyl)isoindole-1,3-dione In tetrahydrofuran at -70℃; for 1h; | 71 To a solution of 2-methylindan-1-one (1.02 g) in tetrahydrofuran (15 ml) was added a solution of 1 M lithium hexamethyl disilazide in tetrahydrofuran (8.4 ml) at -70°C, followed by stirring at the same temperature for 30 minutes. Subsequently, 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione (2.23 g) was added thereto, followed by further stirring at the same temperature for 1 hour. The reaction solution was warmed to 0°C, and a saturated aqueous ammonium chloride solution was then added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=10:1-1:1) to obtain the compound of Preparative Example 71 (422 mg) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tetrahydroxydiboron; trans-[NiIICl2(H2O)4]·2H2O; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; cyclo-octa-1,5-diene; sodium t-butanolate In methanol; toluene at 60℃; for 24h; Glovebox; Inert atmosphere; Sealed tube; | |
80% | With bis(1,5-cyclooctadiene)nickel (0); (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; sodium t-butanolate In toluene at 60℃; for 36h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | General procedure: To a suspension of benzyltriphenylphosphonium bromide (1.63 g, 3.76 mmol) in THF (40 mL) was dropwise added n-BuLi (2.35 mL, 1.6 M in hexanes). After the system was stirred at room temperature for 2 h, indanone (7a, 0.25 g, 1.89 mmol) or its derivative (8a-17a, 1.89 mmol) in THF (10 mL) was added. The reaction mixture was stirred at reflux for 24 h, then, cooled to room temperature, quenched with water (20 mL), and extracted with n-hexane (3 × 30 mL). The organic layers were combined, washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (n-hexane) to give the corresponding products (7b-17b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tert.-butylhydroperoxide; copper(II) oxide; In toluene; at 110℃; for 5h;Schlenk technique; Inert atmosphere; | In a dry Schlenk tube equipped with a magnetron, the copper-oxide catalyst were added different amounts of the oxidizing agent tert-butylhydroperoxide (450.00mg, 1.50mmol), replaced with argon three times, and then weighed <strong>[62708-42-3]2-allylbenzaldehyde</strong> (73.00mg, 0.50mmol), toluene solvent (2ml) placed in a schlenk tube, again replaced with argon three times, the reaction is carried out under argon, the reaction temperature 110 C, reaction time 5 hours. After completion of the reaction the reaction was stopped, cooled to room temperature, filtered, washed with brine three times, the aqueous phase was back-extracted twice with ethyl acetate, the combined organic phase was dried over anhydrous sodium sulfate, and spin dry. Separated by thin layer chromatography, to give the desired product 2-methyl-1-indanone, and the isolated yield is calculated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With dmap; magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 42h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dmap; magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 27h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: ethyl acetate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2,3-dihydro-2-methyl-1H-inden-1-one In tetrahydrofuran at -78℃; for 4h; | 5.1.8 General procedure D: the synthesis of inden-3-yl acetate from indenone General procedure: To a solution of LDA or LHMDS (48.0 mmol, 2.0 equiv) in anhydrous THF (100 mL) was added EtOAc (61.0 mmol, 2.5 equiv) at -78 °C. The mixture was stirred at -78 °C for 30 min. To the resulting mixture was added dropwise a solution of indenone (24.0 mmol, 1.0 equiv) in anhydrous THF (20 mL). The mixture was stirred at -78 °C for another 4 h and then quenched with a saturated aqueous NH4Cl. The mixture was extracted with EtOAc (20 mL × 3). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. To the residue was added HOAc/ H2SO4 (10/1, 40 mL). After stirring for 4 h at room temperature, the mixture was extracted with EtOAc (15 mL × 3). The combined extracts were washed successively with water, saturated NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford inden-3-yl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With (2-hydroxyethyl)(methyl)amine; 5%-palladium/activated carbon; hydrogen In acetonitrile at 20℃; for 1h; | Hydrogenolysis of optically active 2-methyl-2-benzyloxycarbonyl-1-indanone To a solution, at room temperature, of KE* (30% e.e., 50 mg, 0.178 mmol) and 2-(methylamino)ethanol (4 mg, 0.053 mmol) in MeCN (4 mL) was added 5% Pd/C (20 mg). A slow stream of hydrogen was immediately bubbled into the stirred mixture. After 1 h, the solvent was evaporated under reduced pressure. Purification of the residue by flash-chromatographyeluted with petroleum ether/ethyl acetate (9:1) afforded 2-methyl-1-indanone (24 mg), which was racemic according to its analysis using a Chiralcel OB-H column (flow rate: 0.7 mL/min,retention times: 13.3 and 19.4 min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; bis[2-(diphenylphosphino)phenyl] ether; lithium tert-butoxide at 110℃; for 24h; Inert atmosphere; regioselective reaction; | |
66% | With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; potassium <i>tert</i>-butylate at 80℃; for 24h; | |
62% | With trimethylamine-N-oxide; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3; sodium hydroxide at 130℃; for 24h; |
46% | With [(N,N′-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)3][Br]; sodium t-butanolate In toluene at 120℃; for 20h; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sulfuric acid; potassium nitrate at -5℃; for 4h; | 6-Nitro-2,3-dihydro-1H-inden-1-one (10) General procedure: To a solution of 2,3-dihydro-1H-inden-1-one (9, 1.32 g,10.0 mmol) in concentrated sulfuric acid (10 mL), KNO3 (1.21 g, 12.0 mmol) in concentrated sulfuricacid (10 mL) was added dropwise at 5°C in 30 min. The mixture was stirred at 5 C for 4 h.After adding ice water slowly, the mixture was partitioned between water and CH2Cl2. The organiclayer was washed with a saturated aqueous solution of NaHCO3 and brine, dried over anhydrousNa2SO4, and concentrated under vacuum. The residue was purified by column chromatographyon silica gel (eluent: hexane/EtOAc = 7/1) to give 10 (1.10 g, 62%) as a beige solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With pyrrolidine; samarium diiodide In tetrahydrofuran; water at 20℃; for 0.5h; Inert atmosphere; | 2-Methylindan-1-one (5a); Typical Procedure To a solution of SmI2 (0.13 M in THF; 16 mL, 2.1 mmol) wasadded 3a (0.52 mmol, 155.6 mg) followed by H2O (15.6 mmol,0.28 mL) and pyrrolidine (10.4 mmol, 0.86 mL) under an argonatmosphere. The mixture immediately turned white upon additionof pyrrolidine. The mixture was then stirred for 0.5 h at r.t.,then diluted with EtOAc (6 mL) and treated with 0.5 M aq HCl (4mL). The aqueous phase was extracted with EtOAc (2 ×), and theorganic phases were combined, washed with brine, dried (Na2-SO4), filtered, and concentrated. The crude product was purifiedby column chromatography [silica gel, PE-EtOAc (20:1)] to givea yellow oil; yield: 69 mg (91%). 1H NMR (600 MHz, CDCl3):δ = 7.76 (d, J = 7.7 Hz, 1 H), 7.61-7.56 (m, 1 H), 7.45 (d, J = 7.7Hz, 1 H), 7.37 (t, J = 7.4 Hz, 1 H), 3.44-3.36 (m, 1 H), 2.79-2.66(m, 2 H), 1.32 (t, J = 7.0 Hz, 3 H). 13C NMR (151 MHz, CDCl3):δ = 209.4, 153.4, 136.4, 134.6, 127.3, 126.5, 124.0, 42.0, 35.0,16.3. HRMS (EI): m/z [M+] calcd for C10H10O: 146.0726; found:146.0725. |
91% | With pyrrolidine; samarium diiodide; water In tetrahydrofuran at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.3 g | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: ethyl cyanoformate In tetrahydrofuran at -20℃; for 3h; | T-68 Example T-68: Condensation: To a solution of 2-methyl-2,3-dihydro-1H-inden-1-one (1 g, 6.84 mmol) in THF (10 mL) was added sodium bis(trimethylsilyl)amide (1.25 g, 6.84 mmol) slowly. The reaction was stirred at - 78 °C for 1 h. And then ethyl carbonocyanidate (0.68 g, 6.84 mmol) was added slowly. The reaction was stirred at - 20 °C for 3 h. Saturated aqueous NH4Cl (30 mL) and EtOAc (10 mL) was added to the reaction vessel and the resulting biphasic mixture was transferred to a separatory funnel. The layers were separated and the aqueous phase was extracted with EtOAc (2 x 20 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography with an isocratic elution of petroleum ether (95%) and EtOAc (5%) to provide ethyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate (0.3 g, 1.37 mmol) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.2% | With magnesium In diethyl ether at 20℃; for 3h; | 1.1 Synthesis of substituted indenyl In1 0.67 g of magnesium bar was placed in a three-necked flask, 30 mL of anhydrous ethyl ether was added, and 4.10 g of bromobenzene in 30 mL of ethyl ether was added dropwise. 3.20 g of 2-methyl-2,3-dihydro-1-indanone in 40 mL of ethyl ether was added dropwise at room temperature, and the reaction was stirred at room temperature for 3 h. The reaction was quenched with 30 mL of saturated aqueous NH4Cl under ice-water bath and the aqueous phase was extracted with 120 mL of ethyl ether, the organic phase was dried over anhydrous MgS04, spin-dried and dissolved with 70 mL of toluene, 0.50g of hydrated p-toluenesulfonic acid was added , refluxed for 4 h, 30 mL of saturated NaHC03 was added, and the aqueous phase was extracted with 100 mL of petroleum ether, the organic phase was dried over anhydrous MgS04, and the solvent was spin dried, and separated through a column to obtain 3.83 g of pale yellow liquid, yield 85.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With 2,2,6,6-tetramethyl-piperidine; trifluorormethanesulfonic acid; oxygen In m-xylene at 130℃; for 6h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With 2,2,6,6-tetramethyl-piperidine; trifluorormethanesulfonic acid; oxygen In m-xylene at 130℃; for 8h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Diisopropyl chlorophosphate In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; | Phosphoric acid diisopropyl ester 2-methyl-3H-inden-1-yl ester (9b) To a solution of freshly prepared LDA (21 mmol) in THF (50 mL) at -78 °C was added 2-methyl-1-indanone (2.92 g, 20 mmol) in THF solution (10 mL) and the mixture was stirred under an Ar atmosphere for 1h, then the solution of diisopropyl phosphorochloridate (6.0 g, 30 mmol) in THF (5 mL) was dropped at the same temperature. The mixture was stirred and allowed to warm slowly to room temperature. After 1h of stirring at ambient temperature the solvent was evaporated, the residue was dissolved in diethyl ether, washed with saturated NH4Cl and water and dried (MgSO4). Evaporation of solvent afforded the crude reaction mixture. Pure enol phosphate 9b was obtained from column chromatography with petroleum ether/EtOAc (5:1 v/v) as yellow oil (5.21 g, 84 % yield). Rf 0.30 (1:1 hexane/EtOAc); IR (neat, cm-1) νmax=3026, 2977, 2950, 1610, 1510, 1415, 1050, 913; 1H NMR (200 MHz, CDCl3): δ 7.89 - 6.89 (m, 4H), 4.73 (sept, J 6.2Hz, 2H), 3.37 - 3.07 (m, 2H), 2.09 (d, J 2.8Hz, 3H), 1.35 (d, J 6.2Hz, 6H), 1.27 (d, J 6.2Hz, 6H); 13C NMR (50 MHz, CDCl3): δ 142.2 (d, J 9.1Hz), 138.7 (d, J 4.5Hz), 134.2 (s, 1H), 125.2 (d, J 6.5Hz), 124.8 (s), 123.27 (s), 122.1 (s), 116.72 (s), 72.1 (d, J 6.2Hz), 37.4 (s), 22.3 (d, J 5.7Hz), 22.2 (d, J 5.7Hz) 11.0 (s); 31P NMR (81 MHz, CDCl3): δ -6.70 (s). MS (EI): m/z ( %) 310 (20), 225 (33), 145 (20), 128 (100); HRMS m/z calcd for C16H23PO4 [M]+: 310.1334; found [M]+ 310.1329 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With formic acid; ((R,R)-Ts-DENEB)RuCl; triethylamine at 60℃; for 9h; Inert atmosphere; enantioselective reaction; | |
95% | With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H64FeNOP; hydrogen; sodium t-butanolate In isopropyl alcohol at 25 - 30℃; for 12h; Autoclave; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one With 2,2,6,6-tetramethylpiperidinyl-lithium In toluene at 20℃; for 0.25h; Glovebox; Stage #2: 1-Fluoro-3-iodobenzene With di-μ-iodobis(tri-t-butylphosphino)dipalladium(l) In toluene at 20℃; Glovebox; chemoselective reaction; | General procedure for the dinuclear Pd(I)-mediated enolate arylation General procedure: Inside the glovebox, lithium 2,2,6,6-tetramethylpiperidide (LiTMP, 70.7 mg, 0.48 mmol, 1.2 eq.) was dissolved in toluene (1.5 mL) and carbonyl compound (3, 0.48 mmol, 1.2 eq.) was added. After 15 min of stirring at ambient temperature a solution of Pd(I) iodo dimer (2, 3.5 mg, 0.004 mmol, 1 mol% for aryl iodides; 17.4 mg, 0.02 mmol, 5 mol% for aryl bromides) and aryl halide (4, X = I or Br, 0.4 mmol, 1.0 eq.) in toluene (0.5 mL) was added. After 4-18 h of further stirring at ambient temperature (reaction progress was monitored by GCMS), the crude was directly adsorbed onto silica (washing with diethyl ether) and purified by flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: diethyl 1-cyanomethylphosphonate With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; for 0.5h; Stage #2: 2,3-dihydro-2-methyl-1H-inden-1-one In acetonitrile at 20℃; | 5.1.16. 2-(2-methyl-1H-inden-3-yl)acetonitrile (10a) Diethyl cyanomethylphosphonate (13.409 g, 2 equiv) was dissolvedin 65 mL acetonitrile in 0 C, and was dropwise added withDBU (17.272 g, 3 equiv), stirring for 30 min. The mixture was addedwith compound 4a (5 g, 1 equiv) and stirred at room temperatureovernight. After concentrated under reduced pressure, the mixturewas extracted with EtOAc (15 mL *3) and washed with brine(15 mL). The combined organic layers were dried over anhydrousNa2SO4, filtered, and concentrated under reduced pressure. Theresidue was purified by flash chroma-tography to afford compound10a. White solid, 3.5 g, yield: 75%. 1H NMR (600 MHz,CHLOROFORM-d) d 7.39 (d, J 7.34 Hz, 1H), 7.32 (d, J 7.15 Hz, 1H),7.31 (t, J 7.52 Hz, 1H), 7.18 (dt, J 1.19, 7.20 Hz, 1H), 3.54 (s, 2H),3.35 (s, 2H), 2.15 (s, 3H); 13C NMR (151 MHz, CHLOROFORM-d)d 144.1, 143.2, 141.8, 126.6, 125.5, 124.8, 123.5, 118.0, 117.1, 42.9,14.2, 13.9. HRMS (ESI) calcd for C12H11NNa [MNa]: 192.0789;found: 192.0784. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: methyllithium lithium bromide; 2,3-dihydro-2-methyl-1H-inden-1-one In tetrahydrofuran; diethyl ether at 0 - 23℃; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In toluene Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one; ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 23℃; for 3.5h; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In toluene Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 16h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 16h; | |
60% | Stage #1: 2,3-dihydro-2-methyl-1H-inden-1-one; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 23℃; for 5h; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In toluene Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium tetrachloride In hexane at -78 - 20℃; for 2h; | 2.1 (1) (Carbazolyl)methylindene 75mmol of 2-methyl-1-indanone, 150mL of hexane, -78°C, 37.5mmol of titanium tetrachloride and 100mmol of carbazole were added dropwise, and the reaction was carried out at room temperature for 2 hours.After the reaction is over, filter, remove the solvent in the filtrate under reduced pressure and heat 120°C under reduced pressure to remove 2-methyl-1-indanone and by-products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydroxyamino hydrochloride; triethylamine In methanol at 70℃; for 15h; | 14.1 Step 1 Into a 100-mL round-bottom flask, was placed 2-methyl-2,3-dihydroinden-1-one (2.00 g, 13.68 mmol, 1.00 equiv), NH2OH.HCl (0.95 g, 13.68 mmol, 1.00 equiv), Et3N (5.7 mL, 41.04 mmol, 3.00 equiv), MeOH (30.00 mL). The resulting solution was stirred for 15 h at 70 °C in an oil bath. The reaction mixture was cooled to RT. The resulting mixture was concentrated. The residue was applied onto a silica gel column with EtOAc/hexane (1/1). This resulted in 1.8 g (82%) of N-[(1Z)-2-methyl-2,3-dihydroinden-1-ylidene] hydroxylamine as a solid. LC-MS (ES, m/z): [M+H]+=162 |
82% | With hydroxyamino hydrochloride; triethylamine In methanol at 70℃; for 15h; | 14.1 Step 1 Into a 100-mL round-bottom flask, was placed 2-methyl-2,3-dihydroinden-1-one (2.00 g, 13.68 mmol, 1.00 equiv), NH2OH.HCl (0.95 g, 13.68 mmol, 1.00 equiv), Et3N (5.7 mL, 41.04 mmol, 3.00 equiv), MeOH (30.00 mL). The resulting solution was stirred for 15 h at 70 °C in an oil bath. The reaction mixture was cooled to RT. The resulting mixture was concentrated. The residue was applied onto a silica gel column with EtOAc/hexane (1/1). This resulted in 1.8 g (82%) of N-[(1Z)-2-methyl-2,3-dihydroinden-1-ylidene] hydroxylamine as a solid. LC-MS (ES, m/z): [M+H]+=162 |
82% | With hydroxyamino hydrochloride; triethylamine In methanol at 70℃; for 15h; | 14.1 Step 1 Into a 100-mL round-bottom flask, was placed 2-methyl-2,3-dihydroinden-1-one (2.00 g, 13.68 mmol, 1.00 equiv), NH2OH.HCl (0.95 g, 13.68 mmol, 1.00 equiv), Et3N (5.7 mL, 41.04 mmol, 3.00 equiv), MeOH (30.00 mL). The resulting solution was stirred for 15 h at 70 °C in an oil bath. The reaction mixture was cooled to RT. The resulting mixture was concentrated. The residue was applied onto a silica gel column with EtOAc/hexane (1/1). This resulted in 1.8 g (82%) of N-[(1Z)-2-methyl-2,3-dihydroinden-1-ylidene] hydroxylamine as a solid. LC-MS (ES, m/z): [M+H]+=162 |
Tags: 17496-14-9 synthesis path| 17496-14-9 SDS| 17496-14-9 COA| 17496-14-9 purity| 17496-14-9 application| 17496-14-9 NMR| 17496-14-9 COA| 17496-14-9 structure
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