(3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione

Base Information

Chemical Name:(3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione
CAS No.:1320213-49-7
Molecular Formula:C₃₈H₂₈N₂O₄
Molecular Weight:576.651
Hs Code.:

Synonyms:(3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione

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Chemical Property of (3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione

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Technology Process of (3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione

There total 8 articles about (3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione 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:

: C₁₄H₁₅NO₄

: 1320213-49-7
(3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

2.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexanes / 1.25 h / -78 - 20 °C / Inert atmosphere

3.2: 2 h / -78 - -10 °C / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 48 h / -78 - -42 °C / Inert atmosphere

5.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane / 72 h / 50 °C / Darkness; Inert atmosphere

6.1: hydrogenchloride; water / acetone / 0.33 h / 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

8.1: lithium diisopropyl amide / tetrahydrofuran; hexanes / 0.17 h / -78 °C / Inert atmosphere

8.2: 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; water; iodine; silver trifluoromethanesulfonate; caesium carbonate; triethylamine; tri tert-butylphosphoniumtetrafluoroborate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; hexanes; dichloromethane; N,N-dimethyl-formamide; acetone; 5.1: tandem Heck-Suzuki-Miyaura reaction;
DOI:10.1021/ol201812n

Reference yield:

: 1320213-35-1
2-(2-iodo-1H-indol-3-yl)-N-methoxy-N-methylacetamide

: 1320213-49-7
(3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / 1.25 h / -78 - 20 °C / Inert atmosphere

1.2: 2 h / -78 - -10 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 48 h / -78 - -42 °C / Inert atmosphere

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane / 72 h / 50 °C / Darkness; Inert atmosphere

4.1: hydrogenchloride; water / acetone / 0.33 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

6.1: lithium diisopropyl amide / tetrahydrofuran; hexanes / 0.17 h / -78 °C / Inert atmosphere

6.2: 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; water; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; hexanes; dichloromethane; acetone; 3.1: tandem Heck-Suzuki-Miyaura reaction;
DOI:10.1021/ol201812n

Reference yield:

: 1320213-47-5
(Z)-3-((4-methoxyphenyl)(trimethylsilyl)methylene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one

: 1320213-49-7
(3E,3'E)-3,3'-bis(4-methoxybenzylidene)-3,3',4,4'-tetrahydro-[1,1'-bi(cyclopenta[b]indole)]-2,2'(1H,1'H)-dione

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran; hexanes / 0.17 h / -78 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; hexanes;
DOI:10.1021/ol201812n