14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

Base Information

Chemical Name:14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
CAS No.:656836-79-2
Molecular Formula:C₂₈H₂₃NO₈
Molecular Weight:501.493
Hs Code.:

Synonyms:14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

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Chemical Property of 14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

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Technology Process of 14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

There total 46 articles about 14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-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: 97.0%

: 660396-69-0
5,6-dihydro-3,11-diisopropoxy-14-(4-isopropoxy-3-methoxyphenyl)-2,12-dimethoxy-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

: 656836-79-2
14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

Guidance literature:: With aluminium trichloride; In dichloromethane; at 23 ℃; for 2.5h;
DOI:10.1016/j.bmc.2004.01.020

Reference yield: 89.0%

: 190278-32-1
3,10-Bis-benzyloxy-13-(4-benzyloxy-3-methoxy-phenyl)-2,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

: 656836-79-2
14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 ℃; for 18h;
DOI:10.1021/acs.joc.7b01061

Reference yield:

: 6100-60-3
4-methoxybenzene-1,3-diol

: 656836-79-2
14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

Guidance literature:: Multi-step reaction with 11 steps

1: boron trifluoride diethyl etherate / 120 °C

2: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

3: triethylamine / dichloromethane / 2 h / 0 - 20 °C

4: benzyltriethylammonium tribromide / dichloromethane / 0 °C

5: sodium hydrogencarbonate / acetonitrile / 20 h / 20 °C / Reflux

6: trichlorophosphate / 6 h / 0 - 20 °C

7: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; tetrahydrofuran; tert-butyl alcohol / 36 h / 0 - 20 °C

8: methanol; lithium hydroxide / 1 h / 0 - 20 °C

9: dicyclohexyl-carbodiimide / dichloromethane / 6 h / 0 - 20 °C

10: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 20 °C

11: titanium tetrachloride / dichloromethane / 12 h / 0 - 20 °C

With methanol; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; benzyltriethylammonium tribromide; lithium hydroxide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1: |Friedel-Crafts Acylation / 6: |Vilsmeier-Haack Formylation;
DOI:10.1016/j.ejmech.2014.08.038