(E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate

Base Information

Chemical Name:(E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate
CAS No.:94671-23-5
Molecular Formula:C₂₄H₂₄O₉
Molecular Weight:456.449
Hs Code.:

Synonyms:(E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate

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Chemical Property of (E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate

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Technology Process of (E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate

There total 9 articles about (E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate 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: 23.0%

: 29576-13-4
methyl 4-hydroxy-2-butenoate

: 94671-22-4
trans-5,6-dihydro-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxolecarboxylic acid

: 2387-23-7
1,3-Dicyclohexylurea

: 94671-23-5
(E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate

Guidance literature:: With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 4h; Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/jo00207a034

Reference yield:

: 3162-29-6
1-(benzo[d][1,3]dioxol-6-yl)ethanone

: 94671-23-5
(E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) NaH, KH / 1.) THF, 66 deg C, 2.) reflux, 1 h

2: glacial acetic acid, piperidine / benzene / 19 h / Heating

3: 78 percent / AlCl₃ / CH₂Cl₂ / 1 h / 0 °C

4: 97 percent / 50percent aq. HCl / acetone / 48 h / Heating

5: 95 percent / concd. HCl, isoamyl nitrite / ethanol; CH₂Cl₂ / 0 - 25 °C

6: 72 percent / 1N KOH, concd. NH₄OH, 5percent NaOCl / 11 h / 0 - 25 °C

7: 7 percent / 5 h / Irradiation; var. solvents as reagents, var. reaction conditions

8: 69 percent / 1N KOH / methanol; tetrahydrofuran / 48 h / 0 °C

9: 23 percent / dicyclohexylcarbodimide / tetrahydrofuran / 4 h / 0 °C

With piperidine; hydrogenchloride; potassium hydroxide; ammonium hydroxide; sodium hypochlorite; aluminium trichloride; potassium hydride; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; isopentyl nitrite; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; benzene;
DOI:10.1021/jo00207a034

Reference yield:

: 94671-09-7
6,7-dihydro-7-(3,4,5-trimethoxyphenyl)-5H-indeno<5.6-d>-1,3-dioxol-5-one

: 94671-23-5
(E)-3-carbomethoxy-2-propenyl trans-6-(3,4,5-trimethoxyphenyl)cyclobuta(f)-1,3-benzodioxole-5-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / concd. HCl, isoamyl nitrite / ethanol; CH₂Cl₂ / 0 - 25 °C

2: 72 percent / 1N KOH, concd. NH₄OH, 5percent NaOCl / 11 h / 0 - 25 °C

3: 7 percent / 5 h / Irradiation; var. solvents as reagents, var. reaction conditions

4: 69 percent / 1N KOH / methanol; tetrahydrofuran / 48 h / 0 °C

5: 23 percent / dicyclohexylcarbodimide / tetrahydrofuran / 4 h / 0 °C

With hydrogenchloride; potassium hydroxide; ammonium hydroxide; sodium hypochlorite; dicyclohexyl-carbodiimide; isopentyl nitrite; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/jo00207a034