rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

Base Information

• Chemical Name: rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione
• CAS No.: 100848-86-0
• Molecular Formula: C₁₈H₁₆O₂
• Molecular Weight: 264.324
• Mol file: 100848-86-0.mol

Synonyms:

Chemical Property of rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

There total 6 articles about rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-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: 100.0%

2-benzylcyclohexa-2,5-diene-1,4-dione (38940-10-2) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (100848-86-0,117893-87-5)

Guidance literature:

for 0.416667h; Ambient temperature;

Reference yield:

1-nitro-1-phenylmethane (622-42-4) + norbornenoquinone (51175-59-8) → rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (100848-86-0,117893-87-5)

Guidance literature:

With caesium carbonate; In toluene; at 25 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.6b03168

Reference yield:

benzylhydroquinone (1706-73-6) → rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (100848-86-0,117893-87-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Ag₂O

2: 82 percent / methanol / 25 °C

With silver(l) oxide; In methanol; 2: Diels-Alder reaction;

DOI:10.1021/jo026238i

upstream raw materials:

2-benzylcyclohexa-2,5-diene-1,4-dione

cyclopenta-1,3-diene

benzylhydroquinone

hydroquinone

Downstream raw materials:

C₁₈H₁₆O₂

Refernces

• 1、 Eipert, Martin,Maichle-Moessmer, Caecilia,Maier, Martin E.. "Acid-induced rearrangement reactions of reduced benzoquinone cyclopentadiene cycloadducts". . p. 8692 - 8695. Retrieved 2007/10/03.