51175-59-8

Basic information

• Product Name: 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-
• 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
• CAS NO: 51175-59-8
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 218.2058
• Product Categories: C11 to C12;Carbonyl Compounds;Ketones;Building Blocks;C11 to C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 51175-59-8.mol
• Article Data: 46

Chemical Properties

• Melting Point: 77-79 °C(lit.)
• Boiling Point: 317.556°C at 760 mmHg
• Flash Point: 118.895°C
• Appearance: /
• Density: 1.274g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-(CAS DataBase Reference)
• NIST Chemistry Reference: 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-(51175-59-8)
• EPA Substance Registry System: 1 4 4A 8A-TETRAHYDRO-ENDO-1 4-METHANO-(51175-59-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 51175-59-8(Hazardous Substances Data)

Usage

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.

General Description

1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione can be prepared by Diels-Alder reaction of cyclopentadiene and 1,4-benzoquinone.

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 
• 1755-01-7 endo-Dicyclopentadien 
• 4505-38-8 2-cyclohexene-1,4-dione 
• 108-95-2 phenol 
• 678197-26-7 tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-diol 

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 
• 2958-72-7 pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione 
• 60466-75-3 9-methoxy-1,4-anthraquinone 
• 612481-34-2 (1S,4R,4aS,5R,8aR)-8-Methylene-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-ol 
• 638222-51-2 5,8-bis(4-diphenylphosphoranylbenzyloxy)-1,4-dihydro-1,4-methanonaphthalene 
• 850748-18-4 C₂₆H₂₆BrNO₄ 
• 850748-22-0 (3aR,4R,5S,5aR,8aR,8bS)-6-Benzyl-4,5-bis-benzyloxy-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d]oxazol-7-one 
• 850748-21-9 (3aR,4S,5S,6S,7R,7aR)-3-Benzyl-4,5-bis-benzyloxy-6,7-dihydroxy-hexahydro-benzooxazol-2-one 
• 850748-19-5 C₂₆H₂₇NO₄ 
• 850748-13-9 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 

Relevant articles and documents

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.

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.

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

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

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.