2-Butynoic acid, 4-[6-(2-propenyl)-1,3-benzodioxol-5-yl]-4-(3,4,5-trimethoxyphenyl)-, ethyl ester

Base Information

• Chemical Name: 2-Butynoic acid, 4-[6-(2-propenyl)-1,3-benzodioxol-5-yl]-4-(3,4,5-trimethoxyphenyl)-, ethyl ester
• CAS No.: 685881-15-6
• Molecular Formula: C25H26O7
• Molecular Weight: 438.477
• Mol file: 685881-15-6.mol

Synonyms:

Chemical Property of 2-Butynoic acid, 4-[6-(2-propenyl)-1,3-benzodioxol-5-yl]-4-(3,4,5-trimethoxyphenyl)-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Butynoic acid, 4-[6-(2-propenyl)-1,3-benzodioxol-5-yl]-4-(3,4,5-trimethoxyphenyl)-, ethyl ester

There total 1 articles about 2-Butynoic acid, 4-[6-(2-propenyl)-1,3-benzodioxol-5-yl]-4-(3,4,5-trimethoxyphenyl)-, ethyl ester 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: 56.0%

1-allyl-3,4-methylenedioxybenzene (94-59-7) + 4-hydroxy-4-(3,4,5-trimethoxy-phenyl)-but-2-ynoic acid ethyl ester (118741-50-7) → 4-(6-allyl-benzo[1,3]dioxol-5-yl)-4-(3,4,5-trimethoxy-phenyl)-but-2-ynoic acid ethyl ester (685881-15-6) + (10-ethoxycarbonylethynyl-1,2,3,5,6,7-hexamethoxy-9,10-dihydro-anthracen-9-yl)-propynoic acid ethyl ester

Guidance literature:

With silver(I) hexafluorophosphate; (dppm)Re(O)Cl₃; In nitromethane; at 50 ℃; for 4h;

DOI:10.1021/ol049649p

Reference yield: 76.0%

4-(6-allyl-benzo[1,3]dioxol-5-yl)-4-(3,4,5-trimethoxy-phenyl)-but-2-ynoic acid ethyl ester (685881-15-6) → 4-(6-allyl-benzo[1,3]dioxol-5-yl)-3-iodo-4-(3,4,5-trimethoxy-phenyl)-but-2-enoic acid ethyl ester (685881-28-1)

Guidance literature:

With acetic acid; sodium iodide; at 115 ℃; for 4.5h;

DOI:10.1021/ol049649p

Reference yield:

4-(6-allyl-benzo[1,3]dioxol-5-yl)-4-(3,4,5-trimethoxy-phenyl)-but-2-ynoic acid ethyl ester (685881-15-6) → (±)-β-apopicropodophyllin (59123-24-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 76 percent / acetic acid; sodium iodide / 4.5 h / 115 °C

2.1: 77 percent / DIBAL-H / CH₂Cl₂ / 0 - 20 °C

3.1: 91 percent / triphenylphosphine; silver(I) carbonate; palladium(II) acetate / benzene / 1 h / Heating

4.1: 89 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

5.1: 80 percent / oxygen; 5,10,15,20-tetraphenylporphyrin / CCl₄ / 7 h / 0 °C / Irradiation

6.1: 96 percent / aluminum amalgam / tetrahydrofuran; H₂O / 2.5 h / 20 °C

7.1: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

8.1: sodium hydrogen carbonate; lead tetraacetate / CH₂Cl₂ / 0.25 h / 0 °C

8.2: 39 percent / pyridinium dichromate / CH₂Cl₂ / 0.5 h

With lead(IV) acetate; dmap; aluminium amalgam; tetrabutyl ammonium fluoride; oxygen; palladium diacetate; 5,15,10,20-tetraphenylporphyrin; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; triphenylphosphine; silver carbonate; sodium iodide; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; benzene; 3.1: Heck reaction;

DOI:10.1021/ol049649p

upstream raw materials:

1-allyl-3,4-methylenedioxybenzene

4-hydroxy-4-(3,4,5-trimethoxy-phenyl)-but-2-ynoic acid ethyl ester

Downstream raw materials:

4-(6-allyl-benzo[1,3]dioxol-5-yl)-3-iodo-4-(3,4,5-trimethoxy-phenyl)-but-2-enoic acid ethyl ester

(±)-β-apopicropodophyllin

4-(6-allyl-benzo[1,3]dioxol-5-yl)-3-iodo-4-(3,4,5-trimethoxy-phenyl)-but-2-en-1-ol