(3aR,4R,10E,12aS)-3a,4,8,9,12,12a-Hexahydro-11-methyl-3-methylene-4,7-metheno-6H-furo[3,2-c]oxacycloundecin-2,6(3H)-dione

Base Information

• Chemical Name: (3aR,4R,10E,12aS)-3a,4,8,9,12,12a-Hexahydro-11-methyl-3-methylene-4,7-metheno-6H-furo[3,2-c]oxacycloundecin-2,6(3H)-dione
• CAS No.: 22391-22-6
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.29
• Mol file: 22391-22-6.mol

Synonyms:6H-4,7-Methenofuro[3,2-c]oxacycloundecin-2,6(3H)-dione,3a,4,8,9,12,12a-hexahydro-11-methyl-3-methylene-, [3aR-(3aR*,4R*,10E,12aS*)]-;Germacra-1(10),4,11(13)-triene-12,15-dioic acid, 6a,8a-dihydroxy-, di-g-lactone, (E)- (8CI); Isabelin

Chemical Property of (3aR,4R,10E,12aS)-3a,4,8,9,12,12a-Hexahydro-11-methyl-3-methylene-4,7-metheno-6H-furo[3,2-c]oxacycloundecin-2,6(3H)-dione

Chemical Property:

• PSA: 52.60000
• LogP: 2.06620

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,10E,12aS)-3a,4,8,9,12,12a-Hexahydro-11-methyl-3-methylene-4,7-metheno-6H-furo[3,2-c]oxacycloundecin-2,6(3H)-dione

There total 5 articles about (3aR,4R,10E,12aS)-3a,4,8,9,12,12a-Hexahydro-11-methyl-3-methylene-4,7-metheno-6H-furo[3,2-c]oxacycloundecin-2,6(3H)-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: 32.0%

(6R,7S,8S)-6,15-dihydroxygermacra-1(10),4,11(13)-trien-8,12-olide (26931-87-3) → isabelin (22391-22-6,74244-07-8,75363-38-1,75363-39-2,76985-40-5) + 6α-hydroxy-15-oxogermacra-1(10)E,4Z,11(13)-trien-12,8α-olide

Guidance literature:

With dipyridinium dichromate; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1002/mrc.1352

Reference yield:

photoisabelin (27548-70-5,75363-37-0) → (+/-)-pyroisabelin (22391-22-6,74244-07-8,75363-38-1,75363-39-2,76985-40-5) + (+/-)-isabelin (22391-22-6,74244-07-8,75363-38-1,75363-39-2,76985-40-5)

Guidance literature:

In toluene; at 200 ℃; for 0.666667h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00540a029

Reference yield:

photoisabelin (27548-70-5,75363-37-0) → (+/-)-pyroisabelin (22391-22-6,74244-07-8,75363-38-1,75363-39-2,76985-40-5) + (+/-)-isabelin (22391-22-6,74244-07-8,75363-38-1,75363-39-2,76985-40-5)

Guidance literature:

In toluene; at 200 ℃; for 0.666667h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00540a029

upstream raw materials:

photoisabelin

(6R,7S,8S)-6,15-dihydroxygermacra-1⁽¹⁰⁾,4,11⁽¹³⁾-trien-8,12-olide

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