51175-59-8

Usage

Uses

Used in Chemical Synthesis:
1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione is used as a key intermediate in the synthesis of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione, also known as the 'cage' compound. This synthesis is achieved through the intramolecular [2+2]-photocycloaddition reaction, which allows for the formation of complex molecular structures with potential applications in various fields.

InChI:InChI=1/C11H10O2/c12-8-3-4-9(13)11-7-2-1-6(5-7)10(8)11/h1-4,6-7,10-11H,5H2/t6-,7+,10+,11-

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 106-51-4 p-benzoquinone 
• 78548-82-0 1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 
• 678197-26-7 tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-diol 
• 108-95-2 phenol 
• 4505-38-8 2-cyclohexene-1,4-dione 
• 1755-01-7 endo-Dicyclopentadien 

Downstream Products

• 16144-91-5 1,2,3,4-tetrahydro-1,4-methanonaphthalene-5,8-diol 
• 3090-47-9 p-dihydroxybenzonorbornadiene 
• 542-92-7 cyclopenta-1,3-diene 
• 106-51-4 p-benzoquinone 
• 55975-64-9 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 
• 2435-32-7 6,7-epoxy-1,4,4a,6,7,8a-hexahydro-1,4-methano-naphthalene-5,8-dione 
• 2958-72-7 Cookson's diketone 
• 100897-81-2 (1S,2S,7R,8R)tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione 
• 2958-72-7 pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-8,11-dione 
• 2958-72-7 pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione 
• 7213-65-2 5,8-diacetoxy-1,4-dihydro-1,4-methylenonaphthalene 
• 4453-90-1 1,4-dihydro-1,4-methanonaphthalene 
• 130029-38-8 1a,2,2a,6a,7,7a-hexahydro-2,7-methanonaphth[2,3-b]oxirene-3,6-dione 
• 56061-32-6 (+/-)-D₃-trishomocubanone 

Relevant academic research and scientific papers

Diels-Alder reactions of masked p-benzoquinones

Phenylthiomonoketal 3 works effectively as masked p-benzoquinone in Diels-Alder reactions. These cycloadditions may be performed with certain Lewis acid catalysts and give rise exclusively to endo adducts with a good to excellent anti-facial selectivity. 2000 Elsevier Science Ltd.

A model synthesis of the bicyclic core structure of the furanoheliangolide sesquiterpenes

A bicyclo[6.2.1]undecane structure, a model for the core structure of several biologically active furanoheliangolide sesquiterpenes, was synthesized through a retro-aldol reaction from a tricyclo-[6.2.1.02,7]undecane. The required tricyclic compound was prepared by a Diels-Alder reaction followed by minor transformations. (C) 2000 Elsevier Science Ltd.

Revisiting the stability of endo/exo diels-alder adducts between cyclopentadiene and 1,4-benzoquinone

In this work it is presented a detailed theoretical analysis of the relative stability of endo/exo Diels-Alder adducts formed by the reaction between cyclopentadiene (1) and 1,4-benzoquinone (2). The intrinsic reaction coordinate (IRC) showed the existence of only one transition state for the reaction studied, for both endo 3 and exo 4 adducts. The energies of both adducts were obtained at high level of theory (CBS-Q) confirming that the endo adduct is more stable than exo, which is in the opposite way to the observed in reactions that usually follow Alder's rule. An electronic structure analysis was performed through NBO methodology, indicating that the attractive delocalization interaction predominates over the steric repulsive interaction in the endo adducts. In summary, for the studied cycloaddition reaction the endo adduct is the thermodynamic and kinetic product, which can be also confirmed by experimental data mentioned in this work.

Diels-Alder reactions in confined spaces: The influence of catalyst structure and the nature of active sites for the retro-Diels-Alder reaction

Diels-Alder cycloaddition between cyclopentadiene and p-benzoquinone has been studied in the confined space of a pure silica zeolite Beta and the impact on reaction rate due to the concentration effect within the pore and diffusion limitations are discussed. Introduction of Lewis or Br?nsted acid sites on the walls of the zeolite strongly increases the reaction rate. However, contrary to what occurs with mesoporous molecular sieves (MCM-41), Beta zeolite does not catalyse the retro-Diels-Alder reaction, resulting in a highly selective catalyst for the cycloaddition reaction.

1 Hand 13 C NMR spectral data of bioactive cage-like polycyclic compounds

Bioactive cage-like polycyclic compounds have attracted the attention of several research groups because of their unique appearance and their biological activities. Their structures were established on the basis of 1 HNMR and 13 CNMR

Diels-Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds

Diels-Alder reactions between cyclopentadiene analogs and p-benzoquinone were explored in water and yielded 83-97% product, higher than the results reported in water with a catalyst or cetrimonium bromide (CTAB) micelles. The novel adduct 10 was synthesized and further used to synthesize the bi-cage hydrocarbon 4,4′-spirobi[pentacyclo[5.4.0.02,6.03,10.05,9]undecane], which has a high density (1.2663 g cm-3) and a high volumetric heat of combustion (53.353 MJ L-1). Four novel bi-cage hydrocarbon compounds were synthesized in water using this method starting from 2,2′-bi(p-benzoquinone) and cyclopentadiene analogs.

Open and rearranged norbornane derived polycyclic cage molecules as potential neuroprotective agents through attenuation of MPP+- and calcium overload-induced excitotoxicity in neuroblastoma SH-SY5Y cells

The neuroprotective effects of closed polycyclic cage molecules such as NGP1-01, memantine and amantadine have been extensively explored. These effects are mostly linked to the antagonism of the N-methyl-D-aspartate (NMDA) receptor- and the blockage of vo

Synthesis of 4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione derivatives as lead scaffolds for neuroprotective agents

Neurodegenerative disorders are characterised by progressive loss of neuronal functions. Of the proposed mechanisms, excitotoxicity, mediated by prolonged glutamate activation and calcium overload, is prominent. NGP1-01, a polycyclic cage amine, and tricyclo[6.2.1.02,7]undec-9-ene-3,6-dione have been shown to display calcium-modulating properties. In this study, we synthesised structurally-related 4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione as the base scaffold, and incorporated various functional moieties through aminolysis, to afford a series of imide derivatives. All final compounds were obtained in yields between 47-97% and their structures were confirmed by NMR, IR and MS. These structurally-related derivatives could potentially act as neuroprotective agents. Additionally, their synthetic versatilities could make them precursors, as lead compounds, to potential pharmacologically-active agents.

Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.

NORBORNENE-BASED COMPOUND AND METHOD OF PREPARING THE NORBORNENE-BASED COMPOUND

The present invention relates to norbornene-based compound. The present invention provides the norbornene-based compound capable of imparting improved impact performance, heat resistance, and excellent transparency to a copolymer prepared by incorporating a norbornene-based monomer into a benzene ring.COPYRIGHT KIPO 2018