(4aS)-4aα,5,6,7,8,8a,9,9aα-Octahydro-3,8aβ-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one

Base Information

• Chemical Name: (4aS)-4aα,5,6,7,8,8a,9,9aα-Octahydro-3,8aβ-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one
• CAS No.: 16641-51-3
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 16641-51-3.mol

Synonyms:(4aS)-4aα,5,6,7,8,8a,9,9aα-Octahydro-3,8aβ-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one;8-Epiasterolide

Chemical Property of (4aS)-4aα,5,6,7,8,8a,9,9aα-Octahydro-3,8aβ-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS)-4aα,5,6,7,8,8a,9,9aα-Octahydro-3,8aβ-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one

There total 23 articles about (4aS)-4aα,5,6,7,8,8a,9,9aα-Octahydro-3,8aβ-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one 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: 63.0%

1,3-dimethoxypropan-2-one (18664-32-9) + (+/-)-8a-methyl-5-methylene-octahydro-naphthalen-2(1H)-one (3241-65-4,42246-07-1,71883-98-2,74364-44-6) → 4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one (3241-66-5,16641-51-3,73069-14-4,74111-89-0,94163-11-8)

Guidance literature:

With tributyl-amine; titanium tetrachloride; In dichloromethane; at -78 - 20 ℃; for 17h;

DOI:10.1016/j.tetlet.2015.08.045

Reference yield: 35.0%

(+/-)-atractylon (3484-43-3,6989-21-5,98309-94-5) → (+/-)-3,8a-dimethyl-5-methylene-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-b]furan-2(3H)-one + 4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one (3241-66-5,16641-51-3,73069-14-4,74111-89-0,94163-11-8) + 9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one (94204-13-4) + (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione (182426-37-5)

Guidance literature:

With air; In methanol; at 20 ℃; for 840h; Further byproducts given;

DOI:10.1021/jo0488053

Reference yield:

→ eudesma-4(15),7(11)-dien-8α,12-olide (3241-66-5,16641-51-3,73069-14-4,74111-89-0,94163-11-8)

Guidance literature:

ueber mehrere Stufen;

upstream raw materials:

(3aR,4aS,8aR,9aS)-3,8a-Dimethyl-5-methylene-3-phenylsulfanyl-decahydro-naphtho[2,3-b]furan-2-one

(+/-)-atractylon

1,2,3,4,5,8-hexahydro-1-oxo-6-methoxynaphthalene

1,2,3,4,5,8-hexahydro-1-hydroxy-6-methoxynaphthalene

Downstream raw materials:

(+/-)-atractylon

(+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a-hexahydro-4H-naphtho[2,3-b]furan-2-one

3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

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