Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione

Base Information

• Chemical Name: Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione
• CAS No.: 2816-25-3
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.226
• NSC Number: 108091
• DSSTox Substance ID: DTXSID70950902
• Nikkaji Number: J2.058.364I
• Mol file: 2816-25-3.mol

Synonyms:2816-25-3;endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione;endo-(2s,7R)-Tricyclo[6.2.2.0(2,7)]-4,9-dodecadiene-3,6-dione;NSC108091;ghl.PD_Mitscher_leg0.295;SCHEMBL2545104;DTXSID70950902;NSC 108091;NSC-108091;Tricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione;1,4,4a,8a-Tetrahydro-1,4-ethanonaphthalene-5,8-dione;5,8-Ethano-4a,5,8,8a-tetrahydronaphthalene-1,4-dione

Chemical Property of Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione

Chemical Property:

• Vapor Pressure: 0.000152mmHg at 25°C
• Boiling Point: 331.8°Cat760mmHg
• Flash Point: 124.4°C
• Density: 1.218g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 188.083729621
• Heavy Atom Count: 14
• Complexity: 331

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C=CC1C3C2C(=O)C=CC3=O

Technology Process of Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione

There total 5 articles about Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-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: 70.0%

cyclohexa-1,3-diene (1165952-91-9) + benzoic acid (65-85-0,8013-63-6) → tricyclo[6.2.2.0(2,7)]dodeca-4,9-diene-3,6-dione (2816-25-3,76035-69-3) + cis-1-benzoyloxy-4-chloro-2-cyclohexene (129584-33-4)

Guidance literature:

With lithium benzoate; p-benzoquinone; lithium chloride; lithium tetrachloropalladate(II); In acetone; for 14h; Yields of byproduct given;

Reference yield:

palladium diacetate (3375-31-3) + cyclohexa-1,3-diene (1165952-91-9) + benzoic acid (65-85-0,8013-63-6) + p-benzoquinone (106-51-4) → 4-(acetoxy)cyclohex-2-en-1-yl acetate (20117-77-5) + C15H16O4 + endo-tricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione (2816-25-3,69685-89-8,76035-69-3) + C20H18O4 + C20H18O4 + cyclohexene (110-83-8) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

In acetone; at 20 ℃; diastereoselective reaction;

DOI:10.1002/anie.200901614

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) + benzoic acid (65-85-0,8013-63-6) + p-benzoquinone (106-51-4) → endo-tricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione (2816-25-3,69685-89-8,76035-69-3) + trans-1,4-dibenzoyloxy-2-cyclohexene (77300-23-3,129584-26-5) + cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate (77300-23-3,881832-47-9)

Guidance literature:

With dibenzoatopalladium(II); In acetone; at 21.1 ℃; optical yield given as %de; diastereoselective reaction;

DOI:10.1002/anie.200901614

upstream raw materials:

acetic acid

cyclohexa-1,3-diene

benzoic acid

p-benzoquinone

Downstream raw materials:

(3aR,4R,7S,7aR)-1-Oxo-1,4,7,7a-tetrahydro-4,7-ethano-indene-3a-carboxylic acid

endo-tricyclo[6.2.2.0^2,7]dodec-9-ene-3,6-dione bis(tosylhydrazone)

pentacyclo<6.4.0.0^2,7.0^3,11.0^6,10>dodecane-9,12-dione

Pentacyclo<6.4.0.0^2,7.0^3,11.0^6,10>dodecane-9,12-dione