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inquiryThe 2, 6-dimethyl-1-indanone is an important raw material of triazinyl indene amine, and the main synthetic route at present is to prepare the triazinyl indene amine by using p-methyl benzyl chloride as a raw material through four steps of condensati
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inquiry2-methyl-3-p-tolyl-propionyl chloride
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 10℃; for 3h; | 94.6% |
With aluminum (III) chloride In dichloromethane at 0℃; for 4h; Heating / reflux; | 89% |
α-methyl-β-(4-methylphenyl)propionic acid
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
With polyphosphoric acid at 80℃; for 12h; Friedel-Crafts Acylation; | 87% |
With PPA at 100℃; for 3h; | 1.12 g |
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 View Scheme |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In 1,2-dichloro-ethane at 80℃; for 4h; | 82% |
2,5-dimethyl-α-chloropropiophenone
A
1-(2,5-dimethylphenyl)propan-1-one
B
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
In tert-butyl alcohol for 16h; Quantum yield; Irradiation; other solvent; | A 6% B 81% |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
With methanol; sodium hydroxide at 20℃; for 24h; | 81% |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; 1-Phenylethanol; potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In toluene at 100℃; for 16h; Inert atmosphere; Sealed tube; | 71% |
Conditions | Yield |
---|---|
aluminium trichloride In toluene Heating; | 67% |
methanol
2,5-dimethyl-α-chloropropiophenone
A
1-(2,5-dimethylphenyl)propan-1-one
B
2,6-dimethylindan-1-one
C
2-(2,5-Dimethyl-phenyl)-propionic acid methyl ester
D
1-(2-Methoxymethyl-5-methyl-phenyl)-propan-1-one
Conditions | Yield |
---|---|
for 16h; Irradiation; | A 4% B 42% C 24% D 28% |
for 16h; Quantum yield; Rate constant; Irradiation; | A 4% B 42% C 24% D 28% |
2,5-dimethyl-α-chloropropiophenone
A
1-(2,5-dimethylphenyl)propan-1-one
B
2,6-dimethylindan-1-one
C
2-(2,5-Dimethyl-phenyl)-propionic acid methyl ester
D
1-(2-Methoxymethyl-5-methyl-phenyl)-propan-1-one
Conditions | Yield |
---|---|
In methanol for 16h; Irradiation; | A 4% B 42% C 24% D 28% |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
With aluminium trichloride; Petroleum ether anschliessendes Erwaermen; |
para-xylene
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / AlCl3 / 0 - 20 °C 2: 42 percent / methanol / 16 h / Irradiation View Scheme |
diethyl 2-methyl-2-(4-methylbenzyl)malonate
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: concd. HCl / acetic acid / 24 h / Heating 2: 1.12 g / polyphosphoric acid / 3 h / 100 °C View Scheme |
4-Methylbenzyl bromide
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: K2CO3 / dimethylformamide / 10 h / 150 °C 2: concd. HCl / acetic acid / 24 h / Heating 3: 1.12 g / polyphosphoric acid / 3 h / 100 °C View Scheme |
2-methyl-3-p-tolylacrylic acid
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 7600.51 Torr 2: polyphosphoric acid / 12 h / 80 °C View Scheme |
4-methyl-benzaldehyde
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / 0.08 h / 0 °C 1.2: 12 h / 160 - 180 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 7600.51 Torr 3.1: polyphosphoric acid / 12 h / 80 °C View Scheme |
4-Methylbenzyl chloride
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium methylate / tetrahydrofuran / 2 h / 50 - 60 °C 1.2: 3 h / 55 - 60 °C 2.1: sodium hydroxide / 3 h / 60 - 65 °C 3.1: thionyl chloride / dichloromethane / 1 h / 35 - 40 °C 4.1: aluminum (III) chloride / dichloromethane / 3 h / 0 - 10 °C View Scheme |
methyl 2-methyl-3-(4-methylphenyl)propanoate
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / 3 h / 60 - 65 °C 2: thionyl chloride / dichloromethane / 1 h / 35 - 40 °C 3: aluminum (III) chloride / dichloromethane / 3 h / 0 - 10 °C View Scheme |
2,3-dihydro-6-methyl-1H-inden-1-one
methyl iodide
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-6-methyl-1H-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; |
methyl 2-iodo-5-methylbenzoate
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / tetrahydrofuran / 12 h / 100 °C / Inert atmosphere; Sealed tube 2: bis(1,5-cyclooctadiene)nickel (0); potassium tert-butylate; potassium phosphate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; 1-Phenylethanol / toluene / 16 h / 100 °C / Inert atmosphere; Sealed tube View Scheme |
formaldehyd
2,6-dimethylindan-1-one
2-(hydroxymethyl)-2,6-dimethyl-2,3-dihydro-1H-inden-1-one
Conditions | Yield |
---|---|
With potassium carbonate In methanol; toluene at 50℃; | 97% |
2,6-dimethylindan-1-one
A
(1S,2S)-2,6-dimethylindan-1-ol
Conditions | Yield |
---|---|
With formic acid; triethylamine; chloro {[(1S,2S)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(mesitylene)ruthenium(II) at 20℃; for 168h; | A 71% B n/a |
2,6-dimethylindan-1-one
1-amino-2-propene
Conditions | Yield |
---|---|
With formic acid; triethylamine; (S,S)-NH2-CH(Ph)-CH(Ph)-N(Ts)-RuCl-(p-cymene) In dichloromethane at 20℃; for 144h; | 60% |
2,6-dimethylindan-1-one
A
7-Bromo-2,6-dimethyl-1-indanone
B
4,7-dibromo-2,6-dimethyl-1-indanone
C
4-bromo-2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
With aluminum (III) chloride; bromine In chloroform at 0℃; for 3h; | A n/a B 10% C n/a |
2,6-dimethylindan-1-one
benzylamine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 71 percent / HCOOH; triethylamine / (S,S)-[RuCl(TsDPEN)(p-cymene)] / 168 h / 20 °C 2.1: diphenylphosphoryl azide / toluene / 0.17 h / 0 °C 2.2: DBU / toluene / 22 h / 0 - 20 °C View Scheme |
2,6-dimethylindan-1-one
(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl-amine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 71 percent / HCOOH; triethylamine / (S,S)-[RuCl(TsDPEN)(p-cymene)] / 168 h / 20 °C 2.1: diphenylphosphoryl azide / toluene / 0.17 h / 0 °C 2.2: DBU / toluene / 22 h / 0 - 20 °C 3.1: 232 mg / Ph3P; H2O / tetrahydrofuran / Heating View Scheme |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 71 percent / HCOOH; triethylamine / (S,S)-[RuCl(TsDPEN)(p-cymene)] / 168 h / 20 °C 2.1: diphenylphosphoryl azide / toluene / 0.17 h / 0 °C 2.2: DBU / toluene / 22 h / 0 - 20 °C 3.1: 232 mg / Ph3P; H2O / tetrahydrofuran / Heating 4.1: 86 percent / triethylamine / CH2Cl2 View Scheme |
2,6-dimethylindan-1-one
(+)-(2S)-2,3-dihydro-2,5-dimethyl-1H-indene-2-methanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr 3: 6.39 g / ethanol; various solvent(s) View Scheme |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr 3: 6.15 g / ethanol; various solvent(s) View Scheme |
2,6-dimethylindan-1-one
(+/-)-2,3-dihydro-2,5-dimethyl-1H-indene-2-methanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr View Scheme |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: p-TsOH / toluene / Heating 2: HCOOH; Et3N / (S,S)-NH2-CH(Ph)-CH(Ph)-N(Ts)-RuCl-(p-cymene) complex / CH2Cl2 / 144 h / 20 °C View Scheme |
2,6-dimethylindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr 3: 6.39 g / ethanol; various solvent(s) 4: 61 percent / pyridine / 20 °C View Scheme |
2,6-dimethylindan-1-one
2-(hydroxymethyl)-2,6-dimethyl-2,3-dihydro-1H-inden-1-one
Conditions | Yield |
---|---|
With potassium carbonate In water; toluene |
formaldehyd
2,6-dimethylindan-1-one
A
(S)-2,3-dihydro-2-(hydroxymehtyl)-2,6-dimethylindane-1-one
B
(R)-2,3-dihydro-2-(hydroxymethyl)-2,6-dimethylindane-1-one
Conditions | Yield |
---|---|
With pyridine; C23H40N4O4; scandium tris(trifluoromethanesulfonate) In water at 20℃; for 24h; enantioselective reaction; |
2,6-dimethylindan-1-one
ethyl 2-(2,5-dimethyl-1H-inden-3-yl)acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 4 h / -78 °C 2.1: acetic acid; sulfuric acid / 4 h / 20 °C View Scheme |
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