rac-(1R,2S,6R,7R)-4,7-dibromotricyclo[5.2.1.0,2,6]deca-4,8-diene-3,10-dione

Base Information

• Chemical Name: rac-(1R,2S,6R,7R)-4,7-dibromotricyclo[5.2.1.0,2,6]deca-4,8-diene-3,10-dione
• CAS No.: 65656-68-0
• Molecular Formula: C₁₀H₆Br₂O₂
• Molecular Weight: 317.964
• European Community (EC) Number: 964-931-2
• Mol file: 65656-68-0.mol

Synonyms:rac-(1R,2S,6R,7R)-4,7-dibromotricyclo[5.2.1.0,2,6]deca-4,8-diene-3,10-dione;EN300-7494155;(1S,2R,6S,7S)-4,7-dibromotricyclo[5.2.1.02,6]deca-4,8-diene-3,10-dione;2408937-98-2;65656-68-0

Chemical Property of rac-(1R,2S,6R,7R)-4,7-dibromotricyclo[5.2.1.0,2,6]deca-4,8-diene-3,10-dione

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 317.87141
• Heavy Atom Count: 14
• Complexity: 424

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2(C3C=C(C(=O)C3C1C2=O)Br)Br
• Isomeric SMILES: C1=C[C@@]2([C@@H]3C=C(C(=O)[C@@H]3[C@H]1C2=O)Br)Br

Technology Process of rac-(1R,2S,6R,7R)-4,7-dibromotricyclo[5.2.1.0,2,6]deca-4,8-diene-3,10-dione

There total 6 articles about rac-(1R,2S,6R,7R)-4,7-dibromotricyclo[5.2.1.0,2,6]deca-4,8-diene-3,10-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: 93.0%

(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal (485318-53-4) → (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione (32846-64-3,65656-68-0)

Guidance literature:

With sulfuric acid; at 20 - 25 ℃; for 25h;

DOI:10.1016/j.bmcl.2013.12.087

Reference yield:

1,4-dioxaspiro[4.4]nonane (176-32-9) → (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione (32846-64-3,65656-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: bromine / 1,4-dioxane / 60 h / 10 - 20 °C / Inert atmosphere

2: sodium hydroxide / methanol / 3 h / Reflux

3: sulfuric acid / 25 h / 20 - 25 °C

With sulfuric acid; bromine; sodium hydroxide; In 1,4-dioxane; methanol;

DOI:10.1016/j.bmcl.2013.12.087

Reference yield:

2,2,5-tribromocyclopentanone ethylene acetal (25834-49-5) → (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione (32846-64-3,65656-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / methanol / 3 h / Reflux

2: sulfuric acid / 25 h / 20 - 25 °C

With sulfuric acid; sodium hydroxide; In methanol;

DOI:10.1016/j.bmcl.2013.12.087

upstream raw materials:

1,4-dioxaspiro[4.4]nonane

2,2,5-tribromocyclopentanone ethylene acetal

(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal

cyclopentanone

Downstream raw materials:

cubane-1,4-dicarboxylic acid

cubane-1,4-dicarboxylic acid dimethyl ester