hexahydropentalene-1,4-dione

Base Information

• Chemical Name: hexahydropentalene-1,4-dione
• CAS No.: 77483-80-8
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.166
• Mol file: 77483-80-8.mol

Synonyms:

Chemical Property of hexahydropentalene-1,4-dione

Chemical Property:

• Vapor Pressure: 0.00776mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 268.3 °C at 760 mmHg
• Flash Point: 99.4 °C
• Density: 1.191 g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of hexahydropentalene-1,4-dione

There total 8 articles about hexahydropentalene-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: 94.0%

octahydropentalene-1,4-diol → cis-bicyclo<3.3.0>octane-2,6-dione (77483-80-8)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1016/j.tetlet.2014.06.049

Reference yield:

octahydropentalene-1,4-diyl diacetate (200725-73-1) → cis-bicyclo<3.3.0>octane-2,6-dione (77483-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide; methanol / 34 h / 20 °C

2: pyridinium chlorochromate / dichloromethane / 8 h / 20 °C

With methanol; pyridinium chlorochromate; potassium hydroxide; In dichloromethane;

DOI:10.1016/j.tetlet.2014.06.049

Reference yield:

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → cis-bicyclo<3.3.0>octane-2,6-dione (77483-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium dichloride; acetic acid / 96 h / 20 °C

2: potassium hydroxide; methanol / 34 h / 20 °C

3: pyridinium chlorochromate / dichloromethane / 8 h / 20 °C

With methanol; acetic acid; pyridinium chlorochromate; potassium hydroxide; palladium dichloride; In dichloromethane;

DOI:10.1016/j.tetlet.2014.06.049

upstream raw materials:

3,6-Dihydroxy-1,3a,4,6a-tetrahydro-pentalene-2,5-dicarboxylic acid di-tert-butyl ester

1,6-di-tert-butyl 3,4-dimethyl 1,3,4,6-hexanetetracarboxylate

1,5-cis,cis-cyclooctadiene

octahydropentalene-1,4-diyl diacetate

Downstream raw materials:

(2S,3aR,4R,6aS)-4-Methyl-2-(3-oxo-butyl)-hexahydro-pentalen-1-one

(r-1H,c-5H)-2,6-Diphenylbicyclo<3.3.0>octa-2,6-dien

(r-1H,c-5H)-c-2,c-6-Diphenylbicyclo<3.3.0>octan-2,6-diol

Refernces

• 1、 Kotha, Sambasivarao,Ali, Rashid,Chinnam, Ajay Kumar. "Diversity-oriented approach to spirocycles via ring-closing metathesis". . p. 4492 - 4495. Retrieved 2014/08/05.