(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

Base Information

Chemical Name:(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate
CAS No.:136612-45-8
Molecular Formula:C₁₆H₁₆O₄
Molecular Weight:272.301
Hs Code.:

Synonyms:(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

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Chemical Property of (E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

Chemical Property:

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Technology Process of (E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

There total 1 articles about (E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate 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:

: 73670-87-8
(E)-hexa-3,5-dien-1-ol

: (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylic anhydride

: 136612-45-8
(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

Guidance literature:: With pyridine; dmap; In dichloromethane; for 18h; Yield given; Ambient temperature;
DOI:10.1039/P19960000571

Reference yield:

: 136612-45-8
(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

: 476-28-8,6835-91-2,19312-40-4,66816-51-1
(±)-lycorine

Guidance literature:: Multi-step reaction with 18 steps

1: 86 percent / hydroquinone / 1,2-dichloro-benzene / 94 h / 235 °C

2: 97 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 97.7 percent / AgNO₃, Celite 545, Na₂CO₃ / H₂O; benzene / 2 h / Heating

4: 1.) aq. K₂CO₃, 2.) I₂, aq. KI / 1.) reflux, 1h, 2.) r.t., 12.5 h

5: 87 percent / p-TsOH*H₂O / CH₂Cl₂ / 4 h / Ambient temperature

6: 98 percent / DBU / benzene / 20 h / Heating

7: 92 percent / p-TsOH*H₂O / CH₂Cl₂; methanol / 5 h / Ambient temperature

8: 63 percent / Jones reagent / acetone / 0.25 h / 0 °C

9: 78.6 percent / Et₃N, diphenylphosphoryl oxide / 4 h / Heating

10: 98 percent / TFA / CH₂Cl₂ / 1 h / Ambient temperature

11: 97.6 percent / NaOMe / methanol / 3 h / Ambient temperature

12: 98.2 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

13: 84.8 percent / MCPBA / CH₂Cl₂ / 42 h / Ambient temperature

14: 1.) NaH, 2.) pyridine / 1.) THF, 40 deg C, 9.5 h, 2.) r.t., 16 h

15: 98.7 percent / NaBH₄ / ethanol / 0.25 h / Heating

16: 98.3 percent / pyridine / 21 h / Ambient temperature

17: 1.) Vitride / 1.) toluene, reflux, 0.5 h, 2.) THF, reflux, 1 h

18: 86.3 percent / aq. NaIO₄ / tetrahydrofuran; methanol / 0.17 h / 40 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; jones reagent; Celite; diphenylphosphoryl oxide; iodine; sodium methylate; sodium hydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; hydroquinone; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; potassium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; benzene;
DOI:10.1039/P19960000571

Reference yield:

: 136612-45-8
(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

: 136612-59-4
(1S*,2R*,3R*)-3-phenylselanyldihydrolycorine

Guidance literature:: Multi-step reaction with 17 steps

1: 86 percent / hydroquinone / 1,2-dichloro-benzene / 94 h / 235 °C

2: 97 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 97.7 percent / AgNO₃, Celite 545, Na₂CO₃ / H₂O; benzene / 2 h / Heating

4: 1.) aq. K₂CO₃, 2.) I₂, aq. KI / 1.) reflux, 1h, 2.) r.t., 12.5 h

5: 87 percent / p-TsOH*H₂O / CH₂Cl₂ / 4 h / Ambient temperature

6: 98 percent / DBU / benzene / 20 h / Heating

7: 92 percent / p-TsOH*H₂O / CH₂Cl₂; methanol / 5 h / Ambient temperature

8: 63 percent / Jones reagent / acetone / 0.25 h / 0 °C

9: 78.6 percent / Et₃N, diphenylphosphoryl oxide / 4 h / Heating

10: 98 percent / TFA / CH₂Cl₂ / 1 h / Ambient temperature

11: 97.6 percent / NaOMe / methanol / 3 h / Ambient temperature

12: 98.2 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

13: 84.8 percent / MCPBA / CH₂Cl₂ / 42 h / Ambient temperature

14: 1.) NaH, 2.) pyridine / 1.) THF, 40 deg C, 9.5 h, 2.) r.t., 16 h

15: 98.7 percent / NaBH₄ / ethanol / 0.25 h / Heating

16: 98.3 percent / pyridine / 21 h / Ambient temperature

17: 1.) Vitride / 1.) toluene, reflux, 0.5 h, 2.) THF, reflux, 1 h

With pyridine; 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; Celite; diphenylphosphoryl oxide; iodine; sodium methylate; sodium hydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; hydroquinone; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; potassium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; benzene;
DOI:10.1039/P19960000571