1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-

Base Information

• Chemical Name: 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-
• CAS No.: 51175-59-8
• Molecular Formula: O2Re
• Molecular Weight: 174.199
• Hs Code.: 2914690090
• Mol file: 51175-59-8.mol

Synonyms:1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-;1,4,4A,8A-tetrahydro-endo-1,4-methano-naphthalene;RHENIUM(IV) OXIDE, 99.7%;Nsc196244

Chemical Property of 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 77-79 °C(lit.)
• Boiling Point: 317.556°C at 760 mmHg
• Flash Point: 118.895°C
• PSA: 34.14000
• Density: 1.274g/cm³
• LogP: 1.13270

Purity/Quality:

99% ^*data from raw suppliers

1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione may be used in the synthesis of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (the ′cage′ compound) via the intramolecular [2+2]-photocycloaddition reaction.

Technology Process of 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-

There total 16 articles about 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO- 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%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + p-benzoquinone (106-51-4) → norbornenoquinone (51175-59-8)

Guidance literature:

In hexane; ethyl acetate; at 0 ℃; for 3.5h;

DOI:10.1016/j.ejmech.2020.112617

Reference yield: 97.0%

2-cyclohexene-1,4-dione (4505-38-8) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → norbornenoquinone (51175-59-8)

Guidance literature:

In dichloromethane; at 0 - 20 ℃;

DOI:10.15227/orgsyn.073.0253

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

upstream raw materials:

cyclopenta-1,3-diene

p-benzoquinone

1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione

tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-diol

Downstream raw materials:

11-methyl-1,4-diphenyl-1,4,4a,5a,6,9,9a,10a-octahydro-1,4-epiazano-6,9-methano-benzo[g]isochromene-3,5,10-trione

5,8-diacetoxy-1,4-dihydro-1,4-methylenonaphthalene

(3aS,4S,5S,7aS)-3-Benzyl-4-benzyloxy-5-hydroxy-3a,4,5,7a-tetrahydro-3H-benzooxazol-2-one

4-Nitro-benzoic acid (1R,4S,4aR,5R,8R,8aS)-8-acetoxy-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-yl ester

Refernces

• 1、 Constantino,Beatriz,Da Silva. "A model synthesis of the bicyclic core structure of the furanoheliangolide sesquiterpenes". . p. 7001 - 7004. Retrieved 2000.
• 2、 Cantín, ángel,Gomez, M. Victoria,De La Hoz, Antonio. "Diels-Alder reactions in confined spaces: The influence of catalyst structure and the nature of active sites for the retro-Diels-Alder reaction". . p. 2181 - 2188. Retrieved 2016.
• 3、 Shi, Yijun,Liu, Xuejing,Han, Ying,Yan, Peng,Bie, Fusheng,Cao, Han. "Diels-Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds". . p. 739 - 745. Retrieved 2019.
• 4、 Egunlusi, Ayodeji O.,Malan, Sarel F.,Joubert, Jacques. "Synthesis of 4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione derivatives as lead scaffolds for neuroprotective agents". . p. 17 - 27. Retrieved 2020/10/30.