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[ CAS No. 1143-38-0 ] {[proInfo.proName]}

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Chemical Structure| 1143-38-0
Chemical Structure| 1143-38-0
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Product Details of [ 1143-38-0 ]

CAS No. :1143-38-0 MDL No. :MFCD00053409
Formula : C14H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 226.23 Pubchem ID :-
Synonyms :
Anthralin;1,8,9-Anthracenetriol;Batridol;NSC 629313;NSC 43970

Safety of [ 1143-38-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1143-38-0 ]

* 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.

  • Downstream synthetic route of [ 1143-38-0 ]

[ 1143-38-0 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 930-88-1 ]
  • [ 1143-38-0 ]
  • [ 125250-08-0 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In tetrahydrofuran for 0.5h;
  • 3
  • [ 1143-38-0 ]
  • [ 15893-42-2 ]
  • [ 151562-49-1 ]
  • 4
  • [ 1143-38-0 ]
  • [ 35364-99-9 ]
  • [ 151562-79-7 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Yield given;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
  • 5
  • [ 1143-38-0 ]
  • [ 56377-72-1 ]
  • [ 151562-82-2 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Yield given;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
  • 6
  • [ 1143-38-0 ]
  • [ 39188-62-0 ]
  • [ 151562-44-6 ]
YieldReaction ConditionsOperation in experiment
40% With pyridine In toluene for 3h; Ambient temperature;
  • 7
  • [ 1143-38-0 ]
  • [ 51842-87-6 ]
  • 1,8-Dihydroxy-10-[3-(3,4-dimethoxyphenyl)-1-oxopropyl]-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With pyridine In toluene at 80℃; for 3h;
  • 8
  • [ 1143-38-0 ]
  • [ 58608-98-3 ]
  • [ 151562-52-6 ]
YieldReaction ConditionsOperation in experiment
36% With pyridine In toluene at 80℃; for 3h;
  • 9
  • [ 1143-38-0 ]
  • [ 64610-11-3 ]
  • [ 151562-84-4 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Yield given;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
  • 10
  • [ 1143-38-0 ]
  • [ 66543-72-4 ]
  • 1,8-Dihydroxy-10-[3-(3,4,5-trimethoxyphenyl)-1-oxo-propyl]-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With pyridine In toluene at 80℃; for 3h;
  • 11
  • [ 1143-38-0 ]
  • [ 74289-63-7 ]
  • [ 151562-81-1 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Yield given;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
  • 12
  • [ 1143-38-0 ]
  • [ 162750-65-4 ]
  • [ 151562-85-5 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Yield given;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
  • 14
  • [ 1143-38-0 ]
  • [ 497-23-4 ]
  • [ 125250-11-5 ]
YieldReaction ConditionsOperation in experiment
91% With isopropylamine In tetrahydrofuran for 5h;
  • 15
  • [ 1143-38-0 ]
  • [ 18496-54-3 ]
  • [ 162750-61-0 ]
YieldReaction ConditionsOperation in experiment
44% With pyridine In toluene at 80℃; for 3h;
  • 16
  • [ 1143-38-0 ]
  • [ 103-80-0 ]
  • [ 151562-41-3 ]
YieldReaction ConditionsOperation in experiment
36% With pyridine In toluene at 80℃; for 3h;
  • 17
  • [ 1143-38-0 ]
  • [ 645-45-4 ]
  • [ 151562-48-0 ]
YieldReaction ConditionsOperation in experiment
40% With pyridine In toluene at 80℃; for 3h;
  • 18
  • [ 1143-38-0 ]
  • [ 4693-91-8 ]
  • [ 151562-43-5 ]
YieldReaction ConditionsOperation in experiment
45% With pyridine In toluene at 80℃; for 3h;
  • 19
  • [ 1143-38-0 ]
  • [ 764-42-1 ]
  • [ 125250-09-1 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In tetrahydrofuran for 7h;
  • 20
  • [ 1143-38-0 ]
  • [ 20371-41-9 ]
  • [ 151562-56-0 ]
YieldReaction ConditionsOperation in experiment
43% With pyridine In toluene at 80℃; for 3h;
  • 21
  • [ 1143-38-0 ]
  • [ 75-36-5 ]
  • [ 3022-61-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine In benzene Heating;
With pyridine In dichloromethane; toluene 1.a (a) (a) 1,8-Dihydroxy-10-acetylanthrone To a solution of 56.5 g (0.25 mol) of purified anthralin in 1750 cm3 of anhydrous toluene being stirred at room temperature, 27.3 cm3 (0.34 mol) of anhydrous pyridine was added first and then 21.4 cm3 (0.3 mol) of acetyl chloride was added dropwise by means of a dropping funnel. Slight heating occurred during addition then, after the end of addition, the mixture was heated to a temperature of around 90° C. for 1 hour. The mixture was cooled and 27.3 cm3 of pyridine and then, dropwise, 21.4 cm3 of acetyl chloride were again added at 30°-35° C. The mixture was then stirred for 1 hour at 85°-90° C. After a check to insure that the anthralin had been transformed to the 10-acetyl derivative, the reaction mixture was cooled to room temperature then washed 3 times with water (250 cm3). The toluene phase was decanted, dried over sodium sulfate and then concentrated to around 300 cm3. The solution was then deposited on a column of silica gel and eluted with toluene and a 1:1 mixture of toluene and methylene chloride. The first fractions were combined and then concentrated under vacuum. The solid obtained was then recrystallized from toluene to yield 21 g of bright-yellow crystals of 1,8-dihydroxy-10-acetylanthrone having a melting point of 146° C. Analysis: C16 H12 O4 Calc.: C 71.63, H 4.51, O 23.85; Found: C 71.44, H 4.34, O 23.97.
  • 22
  • [ 1143-38-0 ]
  • [ 537-73-5 ]
  • E-1,8-dihydroxy-10-[3-(3-hydroxy-4-methoxyphenyl)-1-oxo-2-propenyl]-9(10H)-anthracenone [ No CAS ]
  • 23
  • [ 37859-24-8 ]
  • [ 1143-38-0 ]
  • 10-[(4-bromo-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 24
  • [ 5728-52-9 ]
  • [ 1143-38-0 ]
  • 10-(biphenyl-4-yl-acetyl)-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 25
  • [ 1131-94-8 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-[(3-hydroxy-4-methoxy-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 26
  • [ 86-87-3 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-(naphthalen-1-yl-acetyl)-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 27
  • [ 87-51-4 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-[(1<i>H</i>-indol-3-yl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 28
  • [ 6845-81-4 ]
  • [ 1143-38-0 ]
  • 10-(benzo[1,3]dioxol-5-yl-acetyl)-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 29
  • [ 5462-71-5 ]
  • [ 1143-38-0 ]
  • 4-[2-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-2-oxo-ethyl]-benzonitrile [ No CAS ]
  • 30
  • [ 37051-38-0 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-[(4-iodo-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 31
  • [ 5807-30-7 ]
  • [ 1143-38-0 ]
  • 10-[(3,4-dichloro-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 32
  • [ 7325-46-4 ]
  • [ 1143-38-0 ]
  • {4-[2-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-2-oxo-ethyl]-phenyl}-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With pyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 50℃; for 2h;
  • 33
  • [ 5292-21-7 ]
  • [ 1143-38-0 ]
  • 10-cyclohexylacetyl-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 34
  • [ 622-47-9 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-[2-(4-methylphenyl)-1-oxoethyl]-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 35
  • [ 1143-38-0 ]
  • [ 16188-55-9 ]
  • 1,8-dihydroxy-10-[(4-methylsulfanyl-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
  • 36
  • [ 1143-38-0 ]
  • [ 32857-62-8 ]
  • 1,8-dihydroxy-10-[(4-trifluoromethyl-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 37
  • [ 1143-38-0 ]
  • [ 17078-28-3 ]
  • 10-[(4-dimethylamino-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 38
  • [ 1143-38-0 ]
  • [ 1026005-61-7 ]
  • 1,8-dihydroxy-10-[4-(4-methoxy-benzyloxy)-phenyl]-acetyl}-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 39
  • [ 1143-38-0 ]
  • [ 81196-09-0 ]
  • {4-[2-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-2-oxo-ethyl]-phenyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 40
  • [ 1143-38-0 ]
  • [ 142667-04-7 ]
  • 4-[2-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-2-oxo-ethyl]-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 41
  • [ 1143-38-0 ]
  • ethyl 4-(2-chloro-2-oxoethyl)benzoate [ No CAS ]
  • 4-[2-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-2-oxo-ethyl]-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 42
  • [ 1143-38-0 ]
  • [4-(3-methoxy-benzyloxy)-phenyl]-acetyl chloride [ No CAS ]
  • 1,8-dihydroxy-10-[4-(3-methoxy-benzyloxy)-phenyl]-acetyl}-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 43
  • [ 1143-38-0 ]
  • [ 10313-60-7 ]
  • 10-[(3,4-dimethoxy-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 44
  • [ 1143-38-0 ]
  • [ 25026-34-0 ]
  • 10-[(4-chloro-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 45
  • [ 1143-38-0 ]
  • [ 6834-42-0 ]
  • 1,8-dihydroxy-10-[(3-methoxy-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 46
  • [ 1143-38-0 ]
  • [ 28033-63-8 ]
  • 1,8-dihydroxy-10-[(2-methoxy-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 47
  • [ 1143-38-0 ]
  • [ 10368-35-1 ]
  • 10-[(4-ethoxy-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 48
  • [ 1143-38-0 ]
  • [ 50690-34-1 ]
  • 1,8-dihydroxy-10-[(4-propoxy-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 49
  • [ 1143-38-0 ]
  • 2-[4-(propan-2-yloxy)phenyl]acetyl chloride [ No CAS ]
  • 1,8-dihydroxy-10-[(4-isopropoxy-phenyl)-acetyl]-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 50
  • [ 1143-38-0 ]
  • [ 60003-47-6 ]
  • 10-[(4-butoxy-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 51
  • [ 1143-38-0 ]
  • [ 459-04-1 ]
  • 10-[(4-fluoro-phenyl)-acetyl]-1,8-dihydroxy-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With pyridine In tetrahydrofuran at 20℃; for 4h;
  • 52
  • [ 1143-38-0 ]
  • [ 581-96-4 ]
  • 1,8-dihydroxy-10-(naphthalen-2-yl-acetyl)-10<i>H</i>-anthracen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;
  • 53
  • [ 1143-38-0 ]
  • [ 4521-22-6 ]
  • 1,8-dihydroxy-10-(4-<i>p</i>-tolyl-butyryl)-10<i>H</i>-anthracen-9-one [ No CAS ]
  • 54
  • [ 1143-38-0 ]
  • [ 3282-30-2 ]
  • 1,8-bis(trimethylacetyloxy)-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In tetrahydrofuran at 20℃;
  • 55
  • [ 941-69-5 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-(1-phenyl-2,5-dioxopyrrolidin-3-yl)-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In dichloromethane at -20℃; for 7h;
  • 56
  • [ 1631-26-1 ]
  • [ 1143-38-0 ]
  • (S)-(+)-1-benzyl-3-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-pyrrolidine-2,5-dione [ No CAS ]
  • (R)-(-)-1-benzyl-3-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-pyrrolidine-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at -20℃; for 8h; Title compound not separated from byproducts;
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; optical yield given as %ee; enantioselective reaction;
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; optical yield given as %ee; enantioselective reaction; 4.5. General experimental procedure for the addition of anthrones to maleimides General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 57
  • [ 19844-27-0 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-[1-(3-,4-dichlorophenyl)-2,5-dioxopyrrolidin-3-yl]-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% In dichloromethane at -20℃; for 8h;
  • 58
  • [ 2973-15-1 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-[1-(2-nitrophenyl)-2,5-dioxopyrrolidin-3-yl]-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In dichloromethane at -20℃; for 8h;
  • 59
  • [ 1143-38-0 ]
  • [ 15121-89-8 ]
  • ethyl 2-(1,8-dihydroxy-9-oxo-9,10-dihydroanthracen-10-yl)-4-oxo-4-phenylbutanoate [ No CAS ]
  • ethyl 2-(1,8-dihydroxy-9-oxo-9,10-dihydroanthracen-10-yl)-4-oxo-4-phenylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at -20℃; for 7h; Title compound not separated from byproducts;
  • 60
  • [ 1143-38-0 ]
  • [ 2833-24-1 ]
  • methyl 2-(1,8-dihydroxy-9-oxo-9,10-dihydroanthracen-10-yl)-4-oxopentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In dichloromethane at -20℃; for 6h;
  • 61
  • [ 1143-38-0 ]
  • [ 764-42-1 ]
  • 2-(1,8-dihydroxy-9-oxo-9,10-dihydroanthracen-10-yl)succinonitrile [ No CAS ]
  • 2-(1,8-dihydroxy-9-oxo-9,10-dihydroanthracen-10-yl)succinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at -20℃; for 7h; Title compound not separated from byproducts;
  • 62
  • [ 1143-38-0 ]
  • [ 151562-60-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 26 percent / pyridine / tetrahydrofuran / 4 h / Ambient temperature 2: 80 percent / K2CO3 / methanol / Ambient temperature
Multi-step reaction with 2 steps 1: 36 percent / pyridine / toluene / 3 h / 80 °C 2: 45 percent / H2 / 10percent Pd/C / tetrahydrofuran / 24 h / 760 Torr / Ambient temperature
  • 63
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-<(3,4-dihydroxyphenyl)methylene>-9(10H)-anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With camphor-10-sulfonic acid In toluene 6 Preparation of 10-(3,4-Dihydroxy-benzylidene)-1,8-dihydroxy-10H-anthracen-9-one Example 6 Preparation of 10-(3,4-Dihydroxy-benzylidene)-1,8-dihydroxy-10H-anthracen-9-one A solution of dithranol (452 mg, 2.0 mmol), 3,4-dihydroxybenzadehyde (276 mg, 2.0 mmol), and camphorsulfonic acid (464 mg, 2.0 mmol) in 10 mL toluene was refluxed overnight The solvents were removed under reduced pressure and the residues were chromatographed (silica gel, methylene chloride-methanol 1:0 to 100:1 to 100:2), yielded 190 mg of product (28%). 1H-NMR (300 Hz, D3CCl) δ ppm) 7.47 (t, J=8.0 Hz, 1H), 7.40-7.30 (m, 2H), 7.27-7.10 (m, 2H), 6.95-6.75 (m, 2H), 6.75-6.60 (m, 3H). 13C-NMR (75 Hz, Cl3CD) δ (ppm) 192.8, 162.0, 161.5, 145.1, 144.5, 142.7, 137.8, 136.8,136.8, 136.0, 134.4,129.2,128.7, 121.9, 121.0,116.3,115.8,115.7,115.3, 114.6,114.0. MS (APCI) m/z 347 (M+1, 100).
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 2: 87 percent / pyridine / 0.5 h / 116 °C 3: 78 percent / BBr3 / CH2Cl2 / 24 h / Ambient temperature
  • 64
  • tungsten powder [ No CAS ]
  • H2BAQ [ No CAS ]
  • palladium (Pd) metal [ No CAS ]
  • platinum (Pt) metal [ No CAS ]
  • t-butyl anthrahydroquinone [ No CAS ]
  • t-butyl anthraquinone [ No CAS ]
  • [ 90-44-8 ]
  • [ 1143-38-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In 1-methyl-pyrrolidin-2-one 1 EXAMPLE 1 EXAMPLE 1 A mixture containing 18 wt% t-butyl anthrahydroquinone (H2BAQ) and 7 wt% t-butyl anthraquinone (TBAQ) in n-methyl-2-pyrrolidinone (NMP) is dehydrogenated at 275° C and 72 psia using three catalysts in three separate runs. One catalyst composition is 2.75 wt% platinum (Pt) metal dispersed on a silica support (Grace Grade 57), the second catalyst composition is 2.75 wt% palladium (Pd) metal on a silica support (Grace Grade 57), and the third catalyst composition is 2.75 wt% tungsten (W) metal on the same support. The electronegativities of the Pd, Pt and W metals are 2.20, 2.28, and 2.36, respectively. The electronegativity of the support is estimated to be significantly below 2.30. The selectivity of converting the H2BAQ to hydrogen and TBAQ is 68 mole% using the Pt catalyst, 25 mole% using the Pd catalyst, and 100% using the W catalyst. In each instance, the balance of the H2BAQ is converted to the corresponding anthrone or anthranol and water. These results, as correlated to the electronegativity of the metal catalysts, are illustrated in FIG. 1, and demonstrate that a metal electronegativity greater than 2.30 is sufficient to yield a selectivity to TBAQ and hydrogen of 100 mole % without production of unwanted anthrone or anthranol and water.
  • 65
  • [ 1143-38-0 ]
  • [ 141-75-3 ]
  • [ 75464-11-8 ]
YieldReaction ConditionsOperation in experiment
With pyridine In water; toluene 13.a (a) (a) 1,8-Dihydroxy-10-butyrylanthrone To a stirred suspension of 51 g (0.22 mol) of 1,8-dihydroxyanthrone in 1.5 liters of toluene, kept under an inert atmosphere and shielded from light, 23.8 cm3 of pyridine was first added all at once and then 27.4 cm3 of butyryl chloride was added dropwise over 15 minutes. The mixture was then heated to a temperature of 80°-90° C. for 1 hour. Subsequently, the same quantities as before of pyridine and butyryl chloride (i.e., a total of 2.7 molar equivalents for pyridine and of 2.4 molar equivalents for the acid chloride) were added at room temperature. The reaction mixture was then reheated to 80°-90° C. for 1 hour. After being cooled to room temperature, the mixture was poured into 500 cm3 of acidulated water. The organic phase was decanted, washed with water until the washings became neutral and dried over magnesium sulfate. This phase was then fractionated by chromatography on a silica gel column, using toluene as the mobile phase. The eluted phases were concentrated and poured into hexane, thus causing crystallization of 1,8-dihydroxy-10-butyrylanthrone. The solvent was sucked from this product, which was then dried to yield 20 g of yellow crystals having a melting point of 138° C. Analysis: C18 H16 O4 Calc.: C 72.96, H 5.44, O 21.60; Found: C 72.75, H 5.48, O 21.38.
  • 66
  • [ 1143-38-0 ]
  • [ 79-30-1 ]
  • [ 102768-28-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine In ethyl acetate; toluene 4.a (a) (a) 1,8-Dihydroxy-10-isobutyrylanthrone To a solution of 56.6 g (0.25 mol) of anthralin in 1750 cm3 of absolute toluene and 27.3 cm3 of pyridine, 31.5 cm3 (0.3 mol) of isobutyryl chloride was added with stirring over 30 minutes at room temperature. The reaction mixture was then heated to 85° C. for 1 hour. After this mixture had recooled to room temperature, 27.3 cm3 of pyridine and 31.5 cm3 of isobutyryl chloride were again added. The suspension obtained was then heated to 85°-90° C. for 1 hour. The precipitated pyridinium hydrochloride was eliminated by filtration then washed with toluene. The toluene filtrates were concentrated to around 500 cm3 under reduced pressure, washed several times with water then dried over magnesium sulfate. The product was then fractionated by chromatography on silica gel, using toluene and then a mixture of toluene and ethyl acetate as the mobile phase. The different fractions containing the 1,8-dihydroxy-10-isobutyrylanthrone were then concentrated and recrystallized from a toluene-hexane mixture. In this way 25 g of yellow crystals of 1,8-dihydroxy-10-isobutyrylanthrone having a melting point of 160° C. was obtained. Analysis: C18 H16 O4 Calc.: C 72.97, H 5.44, O 21.59; Found: C 73.00, H 5.42, O 21.77.
  • 67
  • [ 1143-38-0 ]
  • [ 115-11-7 ]
  • Butyl-1,8-dihydroxy-9-(10H)anthracenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In chloroform 3 2-tert. Butyl-1,8-dihydroxy-9-(10H)anthracenone by method A EXAMPLE 3 2-tert. Butyl-1,8-dihydroxy-9-(10H)anthracenone by method A About 7 gm of isobutylene were introduced into a refluxing solution of 11.3 gm of 1,8-dihydroxy-9-(10H)anthracenone in 100 ml of chloroform and 6 ml of sulfuric acid. The resulting mixture was poured into water, and the organic phase was separated and worked up as described in Example 2. 3.9 gm of 2-tert. butyl-1,8-dihydroxy-9-(10H)anthracenone, m.p. 126°-127° C., corresponding to 27% of theory, were obtained.
  • 68
  • [ 6728-26-3 ]
  • [ 1143-38-0 ]
  • [ 1168059-63-9 ]
YieldReaction ConditionsOperation in experiment
93% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction;
  • 69
  • 2-pentenal [ No CAS ]
  • [ 1143-38-0 ]
  • [ 1168059-60-6 ]
YieldReaction ConditionsOperation in experiment
95% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction;
95% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction; 4.2. General experimental procedure for the addition of anthrones to α,β-unsaturated aldehydes General procedure: To a stirred solution of catalyst (S)-III (20 mg, 0.06 mmol) in toluene (2 mL) were added the α,β-unsaturated aldehyde (0.25 mmol) and the anthrone (1a or 1b, 0.30 mmol). The reaction crude was vigorously stirred at -40 °C until the starting anthrone was not detected by 1H NMR. After warming up the reaction flask to room temperature, the reaction crude was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with an artificially constructed racemic mixture of III in toluene at room temperature during 5 days. Enantiomeric purities were directly determined from the crude reaction mixture immediately after complete conversion, because racemization took place at room temperature. This fact precluded in most instances the reliable determination of specific rotations for adducts 3 and 4.
  • 70
  • [ 2463-63-0 ]
  • [ 1143-38-0 ]
  • [ 1168059-64-0 ]
YieldReaction ConditionsOperation in experiment
92% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction;
92% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction; 4.2. General experimental procedure for the addition of anthrones to α,β-unsaturated aldehydes General procedure: To a stirred solution of catalyst (S)-III (20 mg, 0.06 mmol) in toluene (2 mL) were added the α,β-unsaturated aldehyde (0.25 mmol) and the anthrone (1a or 1b, 0.30 mmol). The reaction crude was vigorously stirred at -40 °C until the starting anthrone was not detected by 1H NMR. After warming up the reaction flask to room temperature, the reaction crude was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with an artificially constructed racemic mixture of III in toluene at room temperature during 5 days. Enantiomeric purities were directly determined from the crude reaction mixture immediately after complete conversion, because racemization took place at room temperature. This fact precluded in most instances the reliable determination of specific rotations for adducts 3 and 4.
  • 71
  • [ 1143-38-0 ]
  • [ 123-73-9 ]
  • [ 1168059-57-1 ]
YieldReaction ConditionsOperation in experiment
88% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction;
88% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction; 4.2. General experimental procedure for the addition of anthrones to α,β-unsaturated aldehydes General procedure: To a stirred solution of catalyst (S)-III (20 mg, 0.06 mmol) in toluene (2 mL) were added the α,β-unsaturated aldehyde (0.25 mmol) and the anthrone (1a or 1b, 0.30 mmol). The reaction crude was vigorously stirred at -40 °C until the starting anthrone was not detected by 1H NMR. After warming up the reaction flask to room temperature, the reaction crude was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with an artificially constructed racemic mixture of III in toluene at room temperature during 5 days. Enantiomeric purities were directly determined from the crude reaction mixture immediately after complete conversion, because racemization took place at room temperature. This fact precluded in most instances the reliable determination of specific rotations for adducts 3 and 4.
  • 72
  • pentacarbonyl(1-ethoxy-3-phenylpropyn-1-ylidene)tungsten [ No CAS ]
  • [ 1143-38-0 ]
  • [ 1190307-34-6 ]
YieldReaction ConditionsOperation in experiment
46% With triethylamine In toluene at 20℃; for 3.5h; Inert atmosphere;
  • 73
  • (pentacarbonyl)(phenylethynyl)(ethoxy)carbene chromium(0) [ No CAS ]
  • [ 1143-38-0 ]
  • [ 1190307-34-6 ]
YieldReaction ConditionsOperation in experiment
31% With triethylamine In dichloromethane at 26℃; for 24h; Inert atmosphere;
  • 74
  • [ 941-69-5 ]
  • [ 1143-38-0 ]
  • [ 1242164-91-5 ]
YieldReaction ConditionsOperation in experiment
93% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; optical yield given as %ee; enantioselective reaction;
93% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; optical yield given as %ee; enantioselective reaction; 4.5. General experimental procedure for the addition of anthrones to maleimides General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 75
  • [ 1081-17-0 ]
  • [ 1143-38-0 ]
  • [ 1242103-49-6 ]
YieldReaction ConditionsOperation in experiment
94% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In toluene; at 20℃; for 14h; General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 76
  • [ 1143-38-0 ]
  • [ 13380-67-1 ]
  • [ 1242103-50-9 ]
YieldReaction ConditionsOperation in experiment
91% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In toluene; at 20℃; for 14h; General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 77
  • [ 5153-67-3 ]
  • [ 1143-38-0 ]
  • (S)-1,8-dihydroxy-10-(1-phenyl-2-nitroethyl)anthracen-9(10H)-one [ No CAS ]
  • [ 1242103-51-0 ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at -40℃; for 14h; optical yield given as %ee; enantioselective reaction; 4.4. General experimental procedure for the addition of anthrones to trans-β-nitrostyrenes General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the nitrostyrene (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction crude was vigorously stirred at room temperature (anthrone 1a) or at -40 °C (dithranol 1b) during 14 h. After warming up the reaction flask to room temperature, the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 78
  • [ 5153-67-3 ]
  • [ 1143-38-0 ]
  • 1,8-dihydroxy-10-(1-phenyl-2-nitroethyl)anthracen-9(10H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; 4.4. General experimental procedure for the addition of anthrones to trans-β-nitrostyrenes General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the nitrostyrene (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction crude was vigorously stirred at room temperature (anthrone 1a) or at -40 °C (dithranol 1b) during 14 h. After warming up the reaction flask to room temperature, the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 79
  • [ 1204-35-9 ]
  • [ 1143-38-0 ]
  • [ 1290540-60-1 ]
  • (R)-(-)-1-(3-chlorophenyl)-3-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-pyrrolidine-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; optical yield given as %ee; enantioselective reaction; 4.5. General experimental procedure for the addition of anthrones to maleimides General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 80
  • [ 32620-66-9 ]
  • [ 1143-38-0 ]
  • C31H23NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; 4.5. General experimental procedure for the addition of anthrones to maleimides General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 81
  • [ 505-57-7 ]
  • [ 1143-38-0 ]
  • [ 1168059-63-9 ]
YieldReaction ConditionsOperation in experiment
93% With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In toluene at -40℃; for 240h; optical yield given as %ee; enantioselective reaction; 4.2. General experimental procedure for the addition of anthrones to α,β-unsaturated aldehydes General procedure: To a stirred solution of catalyst (S)-III (20 mg, 0.06 mmol) in toluene (2 mL) were added the α,β-unsaturated aldehyde (0.25 mmol) and the anthrone (1a or 1b, 0.30 mmol). The reaction crude was vigorously stirred at -40 °C until the starting anthrone was not detected by 1H NMR. After warming up the reaction flask to room temperature, the reaction crude was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with an artificially constructed racemic mixture of III in toluene at room temperature during 5 days. Enantiomeric purities were directly determined from the crude reaction mixture immediately after complete conversion, because racemization took place at room temperature. This fact precluded in most instances the reliable determination of specific rotations for adducts 3 and 4.
  • 82
  • (E)-1-methoxy-4-(2-nitrovinyl)benzene [ No CAS ]
  • [ 1143-38-0 ]
  • (S)-1,8-dihydroxy-10-(1-(4-methoxyphenyl)-2-nitroethyl)anthracen-9(10H)-one [ No CAS ]
  • [ 1290540-54-3 ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at -40℃; for 14h; optical yield given as %ee; enantioselective reaction; 4.4. General experimental procedure for the addition of anthrones to trans-β-nitrostyrenes General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the nitrostyrene (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction crude was vigorously stirred at room temperature (anthrone 1a) or at -40 °C (dithranol 1b) during 14 h. After warming up the reaction flask to room temperature, the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 83
  • [ 1143-38-0 ]
  • 1-nitro-4-[(E)-2-nitroeth-1-enyl]benzene [ No CAS ]
  • (S)-1,8-dihydroxy-10-[2-nitro-1-(4-nitrophenyl)ethyl]-10H-anthracen-9-one [ No CAS ]
  • [ 1290540-55-4 ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at -40℃; for 14h; optical yield given as %ee; enantioselective reaction; 4.4. General experimental procedure for the addition of anthrones to trans-β-nitrostyrenes General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the nitrostyrene (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction crude was vigorously stirred at room temperature (anthrone 1a) or at -40 °C (dithranol 1b) during 14 h. After warming up the reaction flask to room temperature, the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 84
  • [ 1143-38-0 ]
  • [ 101671-00-5 ]
  • (S)-1,8-dihydroxy-10-(2-nitro-1-p-tolylethyl)anthracen-9(10H)-one [ No CAS ]
  • [ 1290540-53-2 ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at -40℃; for 14h; optical yield given as %ee; enantioselective reaction; 4.4. General experimental procedure for the addition of anthrones to trans-β-nitrostyrenes General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the nitrostyrene (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction crude was vigorously stirred at room temperature (anthrone 1a) or at -40 °C (dithranol 1b) during 14 h. After warming up the reaction flask to room temperature, the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 85
  • [ 1143-38-0 ]
  • (R)-1-(1-phenylethyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • [ 1290540-62-3 ]
  • [ 1290540-63-4 ]
YieldReaction ConditionsOperation in experiment
With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; for 14h; optical yield given as %de; diastereoselective reaction; 4.5. General experimental procedure for the addition of anthrones to maleimides General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at 20℃; for 14h; optical yield given as %de; diastereoselective reaction; 4.5. General experimental procedure for the addition of anthrones to maleimides General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
Same Skeleton Products
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