(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
• Mol file: 136612-45-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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:

(E)-hexa-3,5-dien-1-ol (73670-87-8) + (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylic anhydride → (E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate (136612-45-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 18h; Yield given; Ambient temperature;

DOI:10.1039/P19960000571

Reference yield:

(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate (136612-45-8) → (±)-lycorine (476-28-8,6835-91-2,19312-40-4,66816-51-1)

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:

(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate (136612-45-8) → (1S*,2R*,3R*)-3-phenylselanyldihydrolycorine (136612-59-4)

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

upstream raw materials:

(E)-hexa-3,5-dien-1-ol

Downstream raw materials:

(1S*,2R*,3R*)-3-phenylselanyldihydrolycorine

(3aS*,4R*,5R*,6S*,7S*,7aS*)-5,6-dihydroxy-7-(3',4'-methylenedioxyphenyl)-4-phenylselanyl-3a,4,5,6,7,7a-hexahydroindolin-2-one

(±)-lycorine

Refernces