3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

Base Information

Chemical Name:3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione
CAS No.:254736-86-2
Molecular Formula:C₂₂H₃₀O₄
Molecular Weight:358.478
Hs Code.:

Synonyms:3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

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Chemical Property of 3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

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Technology Process of 3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

There total 7 articles about 3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-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: 58.0%

: 254428-63-2
1-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2,3,5,6-tetramethoxybenzene

: 254428-64-3
3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione

: 254736-86-2
3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 - 20 ℃; for 5h;
DOI:10.1021/jo9910886

Reference yield:

: 53163-41-0
((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate

: 254736-86-2
3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: 61 percent / SOCl₂; 4-DMAP; pyridine / 1 h / -30 - 0 °C

2.1: 100 percent / KOH / methanol / 1 h / 20 °C

3.1: 84 percent / PDC / CH₂Cl₂ / 4 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 74 percent / tetrahydrofuran; hexane / 0.5 h / 25 °C

5.1: 100 percent / 4-DMAP; pyridine / 24 h / 25 °C

6.1: 93 percent / Li / tetrahydrofuran; liquid ammonia / 0.25 h / -78 °C

7.1: 58 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 5 h / 0 - 20 °C

With pyridine; dmap; potassium hydroxide; dipyridinium dichromate; n-butyllithium; thionyl chloride; ammonium cerium(IV) nitrate; lithium; In tetrahydrofuran; methanol; hexane; dichloromethane; ammonia; water; acetonitrile; 1.1: Dehydration / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Metallation / 4.2: Addition / 5.1: Acetylation / 6.1: Reduction / 7.1: Oxidation;
DOI:10.1021/jo9910886

Reference yield:

: 54632-04-1
albicanol

: 254736-86-2
3-[[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 84 percent / PDC / CH₂Cl₂ / 4 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 74 percent / tetrahydrofuran; hexane / 0.5 h / 25 °C

3.1: 100 percent / 4-DMAP; pyridine / 24 h / 25 °C

4.1: 93 percent / Li / tetrahydrofuran; liquid ammonia / 0.25 h / -78 °C

5.1: 58 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 5 h / 0 - 20 °C

With pyridine; dmap; dipyridinium dichromate; n-butyllithium; ammonium cerium(IV) nitrate; lithium; In tetrahydrofuran; hexane; dichloromethane; ammonia; water; acetonitrile; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Reduction / 5.1: Oxidation;
DOI:10.1021/jo9910886