3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione

Base Information

Chemical Name:3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione
CAS No.:95106-90-4
Molecular Formula:C₂₃H₂₂O₈
Molecular Weight:426.423
Hs Code.:

Synonyms:3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione

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Chemical Property of 3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione

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Technology Process of 3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione

There total 13 articles about 3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-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: 76.0%

: 616-02-4
citraconic acid anhydride

: 1026470-10-9
5-<1-Acetoxy-1-(3',4',5'-trimethoxyphenyl)methyl>-6-trimethylsilylmethyl-1,3-benzodioxole

: 95106-90-4
3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione

: 95458-29-0
3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride

Guidance literature:: With silica gel; In tetrachloromethane; at 50 ℃; for 240h; Yields of byproduct given;
DOI:10.1039/P19930001235

Reference yield:

: 616-02-4
citraconic acid anhydride

: 82792-81-2
1-(3,4,5-trimethoxyphenyl)-5,6-methylenedioxy-1,3-dihydrobenzothiophene-2,2-dioxide

: 95458-29-0
8a-Methyl-5-(3,4,5-trimethoxy-phenyl)-5,5a,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-6,8-dione

: 95106-90-4
3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione

Guidance literature:: With Phthalic acid dibutyl ester; at 160 - 200 ℃; for 3h; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4020(01)83462-1

Reference yield:

: 495-76-1
piperonol

: 95106-90-4
3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / 49percent aq. HBr / 2 h / Ambient temperature

2: 44.93 g / Mg / tetrahydrofuran / 0 °C

3: Br₂, Na₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

4: 1) BuLi / 1) hexane, THF, 2.5 h, -78 deg C, 2) THF, r.t., overnight

5: pyridine / 24 h / Ambient temperature

6: 76 percent / flash silica / CCl₄ / 240 h / 50 °C

With pyridine; n-butyllithium; hydrogen bromide; bromine; silica gel; sodium carbonate; magnesium; In tetrahydrofuran; tetrachloromethane; dichloromethane; water;
DOI:10.1039/P19930001235