A
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With Shvo's Catalyst In acetone at 35℃; for 20h; Air; | A n/a B 95% |
3-hydroxy-2,3-dihydro-1H-inden-1-one
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With Jones reagent In acetone at 20℃; for 2h; | 95% |
2,3-dihydro-1H-indene-1,3-diol
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1,4-dioxane at 20℃; for 0.333333h; | 92% |
Conditions | Yield |
---|---|
With aluminium trichloride In nitrobenzene at 80℃; for 5h; Mechanism; other aromatic acyl chlorides; | 90% |
With aluminium trichloride In nitrobenzene at 80℃; for 5h; | 90% |
3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
In acetonitrile for 1h; Heating; | 90% |
Conditions | Yield |
---|---|
Stage #1: phthalic acid dimethyl ester; ethyl acetate With sodium methylate at 12 - 80℃; Large scale; Stage #2: With hydrogenchloride In water at 45 - 55℃; for 5h; Large scale; | 83.2% |
Conditions | Yield |
---|---|
With manganese(III) Schiff-base; dihydrogen peroxide at 20℃; for 5h; | A 14% B 83% |
With C26H30F6MnN6O6S2; dihydrogen peroxide; acetic acid In acetonitrile at 20℃; for 1h; chemoselective reaction; | A 9% B 61% |
Conditions | Yield |
---|---|
Stage #1: phthalic acid dimethyl ester; acetic acid With sodium methylate at 12 - 80℃; Stage #2: With hydrogenchloride In water at 45 - 55℃; for 5h; | 82.7% |
dimethyl 2,2-di(but-2-yn-1-yl)malonate
A
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With calcium hydride; 1,5-hexadienerhodium(I)-chloride dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; for 15h; Schlenk technique; Inert atmosphere; | A 10% B 76% |
Conditions | Yield |
---|---|
With sodium percarbonate; adogen 464; bis-(tributyltin oxide) dioxochromium(VI); toluene-4-sulfonic acid In acetonitrile at 80 - 83℃; for 20h; | A 4% B 5% C 70% |
With sodium percarbonate; adogen 464; bis-(tributyltin oxide) dioxochromium(VI) In acetonitrile at 80 - 83℃; for 20h; Product distribution; benzylic oxidation with various reagents, solvent dependence; | A 2% B 10% C 60% |
With dipyridinium dichromate; sodium percarbonate; adogen 464 In 1,2-dichloro-ethane at 80 - 83℃; for 20h; | A 6% B 7% C 30% |
Conditions | Yield |
---|---|
With tert.-butylnitrite; N-hydroxyphthalimide In acetonitrile at 80℃; for 24h; Schlenk technique; | 61% |
With tert.-butylnitrite; N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; under 760.051 Torr; for 24h; Schlenk technique; | 61% |
2-(9-xanthylidene)indane-1,3-dione
A
1H-indene-1,3(2H)-dione
B
2-(9-xanthyl)indane-1,3-dione
Conditions | Yield |
---|---|
With thiophenol at 100℃; for 10h; Product distribution; other reagent; | A 12% B 55% |
dimethyl 2,2-di(but-2-yn-1-yl)malonate
A
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With silver tetrafluoroborate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; calcium hydride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; Schlenk technique; Inert atmosphere; | A 27% B 14% C 45% |
With calcium hydride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 27% B 32% C 40% |
With calcium hydride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; Schlenk technique; Inert atmosphere; | A 10% B 39% C 12% |
Conditions | Yield |
---|---|
With dipyridinium dichromate; adogen 464; dihydrogen peroxide; sodium carbonate In various solvent(s) for 24h; Oxidation; Heating; | A 18% B 38% |
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere; | 35% |
2-propylindan-1,3-dione
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
In acetonitrile for 4h; UV-irradiation; | 28% |
INDANE
A
1H-indene-1,3(2H)-dione
B
3-hydroxy-2,3-dihydro-1H-inden-1-one
C
inden-1-one
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; [(pymox-Me2)2RuCl2]+BF4- In water at 20℃; for 2h; | A 5% B n/a C n/a |
Conditions | Yield |
---|---|
With hydrogenchloride |
2-bromo-indan-1,3-dione
A
1H-indene-1,3(2H)-dione
B
2,2-dibromo-indan-1,3-dione
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
With dihydrogen peroxide Uebersaettigen der Loesung mit Schwefelsaeure; |
2,2-bis-(1,3-dioxo-indan-2-yl)-acenaphthen-1-one
A
1H-indene-1,3(2H)-dione
B
2-(2-oxo-acenaphthen-1-ylidene)-indan-1,3-dione
Conditions | Yield |
---|---|
With sulfuric acid |
3-methoxy-1-oxo-indene-2-carboxylic acid ethyl ester
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
at 100℃; |
2-bromo-1,3-dioxo-indan-2-carboxylic acid ethyl ester
A
1H-indene-1,3(2H)-dione
B
2,2-dibromo-indan-1,3-dione
Conditions | Yield |
---|---|
With water |
1H-indene-1,3(2H)-dione
1-(1,3-dioxo-indan-2-yl)-4-(1,3-dioxo-indan-2-ylidene)-3,4-dihydro-2H-pyrrolium betaine
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
at 210 - 220℃; under 0.1 Torr; |
2‑(2‑hydroxybenzylidene)‑1H‑indene‑1,3(2H)‑dione
phenylhydrazine
A
1H-indene-1,3(2H)-dione
B
salicylaldehyde
Conditions | Yield |
---|---|
With aluminium trichloride |
Conditions | Yield |
---|---|
at 1100℃; Mechanism; lower temperature; | |
at 1100℃; flash thermolysis; Yield given; | |
With potassium tert-butylate In tetrahydrofuran |
2-diazo-3-hydroxy-1-indanone
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
tin(ll) chloride In dichloromethane Ambient temperature; |
1,3-indandione anion
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With 4-chlorobenzylmalononitrile; potassium chloride In water; dimethyl sulfoxide at 20℃; Rate constant; var. phenyl-substituted benzylmalononitriles; |
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide; potassium bromide In toluene at 20℃; for 0.5h; | 100% |
With hydroxy(tosyloxy)iodobenzene; copper(ll) bromide In acetonitrile at 0℃; for 0.0833333h; | 90% |
With bromomalononitrile In N,N-dimethyl-formamide at 20℃; for 0.5h; Reagent/catalyst; | 90% |
1H-indene-1,3(2H)-dione
2-aminoacetophenone
10-methyl-11H-indeno[1,2-b]quinolin-11-one
Conditions | Yield |
---|---|
With acetic acid at 130℃; for 4h; | 100% |
With malic acid In neat (no solvent) at 70℃; for 2.4h; Friedlaender Quinoline Synthesis; Green chemistry; | 81% |
With water; acetic acid at 130℃; for 4h; | 50% |
1H-indene-1,3(2H)-dione
3,5-di-t-butyl-4-hydroxybenzaldehyde
(Z)-2-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform for 21h; Knoevenagel reaction; Heating; | 100% |
With sulfuric acid In acetic acid for 51h; Ambient temperature; | 75% |
With piperidine In ethanol for 8h; Knoevenagel Condensation; Reflux; | 51.5% |
With piperidine In acetic acid |
1H-indene-1,3(2H)-dione
(Z)-5a,6,7,9a-Tetrahydro-5a,6-tetramethylene-11-[ethoxycarbonyl(nitro)methylene]naphtho[1',2':4,5]imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; methylene exchange; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1H-indene-1,3(2H)-dione; 4-chlorobenzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1H-indene-1,3(2H)-dione; 1-naphthaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1H-indene-1,3(2H)-dione; 4-hydroxy-benzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1H-indene-1,3(2H)-dione; 4-cyanobenzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1H-indene-1,3(2H)-dione; methyl 4-formylbenzoate With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction; | 100% |
1H-indene-1,3(2H)-dione
3-nitro-benzaldehyde
3′-(3-nitrophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone
Conditions | Yield |
---|---|
With bromocyane; triethylamine In methanol at 0 - 20℃; for 0.00416667h; Sealed tube; | 100% |
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; sodium acetate In ethanol at 20℃; for 0.0333333h; Reagent/catalyst; | 96% |
With dmap; iodine at 20℃; for 1h; Neat (no solvent); Mechanical ball-milling; chemospecific reaction; | 88% |
1H-indene-1,3(2H)-dione
4-nitrobenzaldehdye
3'-(4-nitrophenyl)-dispiro[indan-2,1'-cyclopropane-2',2''-indan]-1,1'',3,3''-tetrone
Conditions | Yield |
---|---|
With bromocyane; triethylamine In methanol at 0 - 20℃; for 0.00416667h; Sealed tube; | 100% |
With dmap; iodine at 20℃; for 1h; Neat (no solvent); Mechanical ball-milling; chemospecific reaction; | 89% |
1H-indene-1,3(2H)-dione
2,4-dichlorobenzaldeyhde
3′-(2,4-dichlorophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone
Conditions | Yield |
---|---|
With bromocyane; triethylamine In methanol at 0 - 20℃; for 0.00416667h; Sealed tube; | 100% |
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; sodium acetate In ethanol at 20℃; for 0.166667h; Reagent/catalyst; | 96% |
formaldehyd
1H-indene-1,3(2H)-dione
dispiro[indene-2,1'-cyclopropane-2',2''-indene]-1,1'',3,3''-tetraone
Conditions | Yield |
---|---|
With bromocyane; sodium ethanolate In methanol at 0 - 20℃; for 0.00416667h; Sealed tube; | 100% |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In water at 20℃; Inert atmosphere; | 99.8% |
1H-indene-1,3(2H)-dione
4-nitrobenzaldehdye
2-(p-nitrobenzylidene)indan-1,3-dione
Conditions | Yield |
---|---|
With L-proline In methanol at 25℃; for 12h; organocatalytic Knoevenagel condensation; | 99% |
In water at 20 - 80℃; Knoevenagel condensation; | 97.5% |
With magnesium oxide at 20℃; for 0.333333h; Knoevenagel condensation; | 94% |
1H-indene-1,3(2H)-dione
2,5-dimethoxybenzaldehyde
2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In ethanol; water at 50 - 60℃; Reagent/catalyst; Solvent; | 99% |
Stage #1: 1H-indene-1,3(2H)-dione With pyridine Stage #2: 2,5-dimethoxybenzaldehyde at 100℃; for 1h; | 75% |
With ethanol |
1H-indene-1,3(2H)-dione
2,4-Dihydroxybenzaldehyde
2-(2,4-dihydroxybenzylidene)-1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With pyridine In ethanol Reflux; | 99% |
In ethanol for 3h; Heating; | 72% |
With hydrogenchloride; acetic acid In water at 20℃; Inert atmosphere; | 43.1% |
With piperidine; ethanol | |
With potassium hydroxide bei der Kondensation; |
1H-indene-1,3(2H)-dione
propargyl bromide
2,2-di(prop-2-yn-1-yl)-1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With caesium carbonate In acetone; toluene at 20℃; for 16h; | 99% |
With potassium hydroxide In water; acetone at 2440℃; for 16h; Reflux; | 93% |
With potassium hydroxide In water at 40℃; for 24h; | 93% |
1H-indene-1,3(2H)-dione
poly{oxy[(E)-but-2-enylene](1,3-indandione-2,2-diyl)[(E)-but-2-enylene]}, Mn=14000; monomer(s): (2Z,7Z)-non-2,7-diene-5-oxa-1,9-ol dibenzoic acid ester; 1,3-indane-2,4-diene
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide; tris(dibenzylideneacetone)dipalladium (0); 1,4-di(diphenylphosphino)-butane In dichloromethane; N,N-dimethyl-formamide Tsuji-Trost reaction; | 99% |
1H-indene-1,3(2H)-dione
allyl alcohol
2,2-diallyl-1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In water; ethyl acetate at 20℃; for 18h; Tsuji-Trost reaction; | 99% |
With Ru(Cp*)(η3-C3H5)(p-CH3C6H5SO3)2 In dichloromethane; acetonitrile at 50℃; for 3h; regioselective reaction; | 89% |
Conditions | Yield |
---|---|
With 1,2-diamino-benzene; rac-Pro-OH In ethanol at 25℃; for 1h; | 99% |
With 2,6-dimethyl-1,4-dihydropyrimidine-3,5-dicarboxylic acid diethyl ester; L-proline In ethanol at 25℃; Knoevenagel/hydrogenation reaction; | 88% |
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In ethanol at 25℃; for 26h; cascade Knoevenagel olefination/hydrogenation reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction; | 88% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 20℃; for 24h; | 99% |
3-(4-bromophenylamino)-5,5-dimethylcyclohex-2-enone
1H-indene-1,3(2H)-dione
2-chloro-benzaldehyde
10-(4-bromophenyl)-5-(2-chlorophenyl)-7,8-dihydro-7,7-dimethyl-5H-indeno[1,2-b]quinolin-9,11(6H,10H)-dione
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 8h; | 99% |
1H-indene-1,3(2H)-dione
5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one
2-nitro-benzaldehyde
7,8-dihydro-7,7-dimethyl-5-(2-nitrophenyl)-10-phenyl-5H-indeno[1,2-b]quinolin-9,11(6H,10H)-dione
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 6h; | 99% |
(5-methyl-pyridin-2-yl)amine
1H-indene-1,3(2H)-dione
pyrimidine-2,4,5,6(1H,3H)-tetraone
5-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-5-hydroxypyrimidine-2,4,6(1H,3H,5H)-trione 2-amino-5-methylpyridinium salt
Conditions | Yield |
---|---|
In chloroform for 1h; Reflux; | 99% |
Conditions | Yield |
---|---|
With aluminum oxide In dichloromethane at 25℃; for 12h; Knoevenagel Condensation; | 99% |
Conditions | Yield |
---|---|
With aluminum oxide In dichloromethane at 25℃; for 12h; Knoevenagel Condensation; | 99% |
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 12h; Solvent; Molecular sieve; diastereoselective reaction; | 99% |
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 12h; Molecular sieve; diastereoselective reaction; | 99% |
1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; | 99% |
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