(+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Base Information

Chemical Name:(+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one
CAS No.:1337985-49-5
Molecular Formula:C₂₇H₂₀ClNO₉
Molecular Weight:537.91
Hs Code.:

(+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Synonyms:

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Chemical Property of (+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

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Technology Process of (+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

There total 5 articles about (+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 72744-56-0
5-bromobenzo[d][1,3]dioxole-4-carboxylic acid

: 1337985-49-5
(+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Guidance literature:: Multi-step reaction with 9 steps

1: sulfuric acid; magnesium sulfate / dichloromethane / 24 h / 20 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium metabisulfite; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 20 h / 100 °C / Inert atmosphere

3: water; N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere

4: toluene-4-sulfonic acid / benzene / 1 h / Reflux

5: potassium osmate(VI) dihydrate; AD-mix-α; methanesulfonamide; water; hydroquinidein 1,4-phthalazinediyl diether / dichloromethane; tert-butyl alcohol / 86 h / 0 °C

6: trifluoroacetic acid

7: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone

8: chloroform / 24 h / 0 - 20 °C

9: tetrabutyl ammonium fluoride

With sodium metabisulfite; potassium osmate(VI) dihydrate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; methanesulfonamide; AD-mix-α; sulfuric acid; tetrabutyl ammonium fluoride; water; magnesium sulfate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; hydroquinidein 1,4-phthalazinediyl diether; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 5: Sharpless dihydroxylation / 7: Pinacol type rearrangement;
DOI:10.1016/j.tet.2011.07.091

Reference yield:

: 1337985-46-2
(+)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b-dihydrobenzo[c]phenanthridin-6(5H)-one

: 1337985-49-5
(+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: chloroform / 24 h / 0 - 20 °C

2: tetrabutyl ammonium fluoride

With tetrabutyl ammonium fluoride; In chloroform;
DOI:10.1016/j.tet.2011.07.091

Reference yield:

: 1337985-23-5
(+)-4b,10b-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,10b,11,12-tetrahydrobenzo[c]phenanthridin-6(5H)-one

: 1337985-49-5
(+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid

2: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone

3: chloroform / 24 h / 0 - 20 °C

4: tetrabutyl ammonium fluoride

With tetrabutyl ammonium fluoride; potassium carbonate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; 2: Pinacol type rearrangement;
DOI:10.1016/j.tet.2011.07.091