5,8-Methano-4abeta,5,8,8abeta-tetrahydro-1,4-naphthoquinone

Base Information

• Chemical Name: 5,8-Methano-4abeta,5,8,8abeta-tetrahydro-1,4-naphthoquinone
• CAS No.: 1200-89-1
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 174.199
• Hs Code.: 2914690090
• European Community (EC) Number: 864-069-6
• Nikkaji Number: J1.480.221E
• Mol file: 1200-89-1.mol

Synonyms:Tricyclo[6.2.1.0,2,7]undeca-4,9-diene-3,6-dione;51175-59-8;AKOS004903267;CS-0233647;5,8-Methano-4abeta,5,8,8abeta-tetrahydro-1,4-naphthoquinone

Chemical Property of 5,8-Methano-4abeta,5,8,8abeta-tetrahydro-1,4-naphthoquinone

Chemical Property:

• Vapor Pressure: 0.000382mmHg at 25°C
• Melting Point: 77-79 °C(lit.)
• Refractive Index: 1.5250 (estimate)
• Boiling Point: 317.6°C at 760 mmHg
• Flash Point: 118.9°C
• PSA: 34.14000
• Density: 1.273g/cm³
• LogP: 1.13270
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 319

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C3C2C(=O)C=CC3=O
• Isomeric SMILES: C1C2C=CC1[C@@H]3[C@H]2C(=O)C=CC3=O
• Uses: 1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione is reduced to 5,8-dihydroxy-1,4-dihydro-1,4-methanonaphthalene (DDMN), a substituted phenol with antioxidant activity and a potential radio-protector.

Technology Process of 5,8-Methano-4abeta,5,8,8abeta-tetrahydro-1,4-naphthoquinone

There total 8 articles about 5,8-Methano-4abeta,5,8,8abeta-tetrahydro-1,4-naphthoquinone 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: 97.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + p-benzoquinone (106-51-4) → 1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (54353-48-9,1200-89-1)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 2.25h;

DOI:10.1002/ejoc.200800218

Reference yield: 95.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + p-benzoquinone (106-51-4) → 1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (1200-89-1,51175-59-8,54353-48-9,100897-81-2)

Guidance literature:

In methanol; at 20 ℃; for 6h;

DOI:10.1021/jo035318z

Reference yield: 94.2%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + p-benzoquinone (106-51-4) → 5,8-Dioxo-1,4-methylen-1,4,5,8,9,10-hexahydro-naphthalin (1200-89-1,51175-59-8,54353-48-9,100897-81-2)

Guidance literature:

at 20 ℃;

DOI:10.1039/c4ra09599e

upstream raw materials:

cyclopenta-1,3-diene

p-benzoquinone

endo-Dicyclopentadien

Downstream raw materials:

benzene-1,4-diyl diacetate

1,4,5,8-tetrahydro-1,4;5,8-dimethano-anthracene-9,10-dione

2-cyclohexene-1,4-dione

pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione

Refernces

• 1、 Mal, Dipakranjan,Ray, Sutapa. "First synthesis of 9,10-dimethoxy-2-methyl-1,4-anthraquinone: A naturally occurring unusual anthraquinone". . p. 3014 - 3020. Retrieved 2008.
• 2、 Marchand,Allen. "". . p. 1596. Retrieved 1974.
• 3、 Rathore, Rajendra,Abdelwahed, Sameh H.. "Soluble cycloannulated tetroxa[8]circulane derivatives: Synthesis, optical and electrochemical properties, and generation of their robust cation-radical salts". . p. 5267 - 5270. Retrieved 2004.
• 4、 Kalepu, Rishir,Mishra, Satyendra. "Lewis acid catalyst system for Diels–Alder reaction". . . Retrieved 2020.
• 5、 Isaacs, Neil S.,Keating, Nicholas. "The Rates of a Diels-Alder Reaction in Liquid and Supercritical Carbon Dioxide". . p. 876 - 877. Retrieved 1992.
• 6、 Zindo, Frank T.,Malan, Sarel F.,Omoruyi, Sylvester I.,Enogieru, Adaze B.,Ekpo, Okobi E.,Joubert, Jacques. "Design, synthesis and evaluation of pentacycloundecane and hexacycloundecane propargylamine derivatives as multifunctional neuroprotective agents". supporting information. p. 83 - 94. Retrieved 2018/12/04.