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CAS No.: | 5707-96-0 |
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Name: | Justicidin B |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C21H16O6 |
Molecular Weight: | 364.354 |
Synonyms: | 9-(3,4-dimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one;UNII-RQQ8T34V5F;9-(3,4-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8h)-one;Retrochinensin;Retrochinesin; |
Density: | 1.376g/cm3 |
Boiling Point: | 593.2°Cat760mmHg |
Flash Point: | 262.2°C |
PSA: | 63.22000 |
LogP: | 3.92310 |
4-(3',4'-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxy-3,4-dihydro-2-naphthoic acid γ-lactone
retrochinensin
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform; benzene for 48h; Heating; | 100% |
2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene
retrochinensin
Conditions | Yield |
---|---|
With 1-Phenylbut-1-en-3-one; dihydridotetrakis(triphenylphosphine)ruthenium In toluene for 10h; Heating; | 94% |
With manganese(IV) oxide In dichloromethane at 20℃; for 48h; | 91% |
2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene
A
1-(3,4-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxynaphthalene-2-carboxylic acid lactone
B
retrochinensin
Conditions | Yield |
---|---|
With barium permanganate In dichloromethane at 20℃; for 48h; | A 19% B 80% |
With bis(pyridine)silver permanganate In benzene for 2h; Heating; | A 18.2% B 56.6% |
With pyridinium chlorochromate In chloroform for 12h; Ambient temperature; | A 53.2% B 25.3% |
With silica gel; silver carbonate In benzene for 3h; Heating; | A 14 mg B 58 mg |
6,7-methylenedioxy-1-(3,4-dimethoxyphenyl)naphthalene-2,3-dicarboxylic acid 2-ethyl ester
retrochinensin
Conditions | Yield |
---|---|
With lithium borohydride; sodium hydride In tetrahydrofuran; 1,4-dioxane for 28h; Heating; | 72% |
α-(trans-3',4'-methylenedioxybenzylidene)-β-(3,4-dimethoxybenzyl)-γ-butyrolactone
retrochinensin
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 24h; Heating; | 70% |
erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone
retrochinensin
Conditions | Yield |
---|---|
With trifluoroacetic acid for 2h; Heating; | 62% |
With trifluoroacetic acid | 60% |
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 0.166667h; Diels-Alder Cycloaddition; Flow reactor; Irradiation; regioselective reaction; | A 17.3% B 52.2% |
1-(3',4'-dimethoxyphenyl)-6,7-methylenedioxynaphthalene-2,3-dicarboxylic anhydride
retrochinensin
Conditions | Yield |
---|---|
With sodium tetrahydroborate | 49.5% |
3,4-methylenedioxyphenylethyne
carbon dioxide
3,4-dimethoxyphenylpropargyl chloride
A
justicidin B
B
retrochinensin
Conditions | Yield |
---|---|
With 18-crown-6 ether; silver(I) iodide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 5h; Molecular sieve; | A 16% B 16% |
erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone
A
retrochinensin
threo-3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone
erythro-3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane for 1h; Product distribution; Ambient temperature; attempted cyclisations of further derivatives with various acids; |