25326-19-6

Usage

InChI:InChI=1/C8H8O3/c9-8-10-6-4-1-2-5(3-4)7(6)11-8/h1-2,4-7H,3H2

Upstream product

• 872-36-6 vinylene carbonate 
• 542-92-7 cyclopenta-1,3-diene 
• 77-73-6 endo-<2+4>-Dicyclopentadien 
• 20224-38-8 bicyclo[2.2.1]hept-5-ene-2,3-diol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 77-73-6 bi(cyclopentadiene) 

Downstream Products

• 17994-26-2 bicyclo[2.2.1]hept-5-ene-2,3-dione 

Relevant academic research and scientific papers

α-Diimine–Palladium Complexes Incorporated in Vinylic-Addition Polynorbornenes: Synthesis and Catalytic Activity

α-Diimine polymeric ligands have been synthesized using the bicyclic norbornane structure, present in vinylic-addition polynorbornene (VA-PNB). The VA-PNB–diimine ligands have been prepared by functionalization of the copolymer obtained by Ni-catalyzed polymerization of norbornene and norbornenylcarbonate. Immobilized palladium complexes of the type VA-PNB–diimine–PdX2 have been prepared, and their catalytic activity has been tested. The trifluoroacetato complex (X = CF3COO) can be used as a recyclable precatalyst in the Suzuki reaction. It is the source of minute amounts of homogeneous palladium active species, which carry out the catalysis with high turnover numbers. The recovered polymeric complex can be reused several times with no significant loss of activity. The polymeric analogue to Brookhart's catalyst, VA-PNB–diimine–PdMeCl, can also polymerize ethylene, although it is less active than its monomeric counterparts.

Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides

Carbocyclic C-nucleosides are quite rare. Our route enables flexible preparation of three classes of these nucleoside analogs from common precursors-properly substituted cyclopentanones, which can be prepared racemic (in six steps) or optically pure (in ten steps) from inexpensive norbornadiene. The methodology allows flexible manipulation of individual positions around the cyclopentane ring, namely highly diastereoselective installation of carbo- and heterocyclic substituents at position 1′, orthogonal functionalization of position 5′, and efficient inversion of stereochemistry at position 2′. Newly prepared carbocyclic C-analog of tubercidine, profiled in MCF7 (breast cancer) and HFF1 (human foreskin fibroblasts) cell cultures, is less potent than tubercidine itself, but more selectively toxic toward the tumorigenic cells.

Microwave-assisted solvent-free Diels-Alder reaction - A fast and simple route to various 5,6-substituted norbornenes and polychlorinated norbornenes

A series of 5,6-substituted norbornenes and 5,6-substituted polychlorinated norbornenes was prepared by using a microwave-assisted Diels-Alder reaction. This procedure proved very versatile, fast, and with an easy workup step, and therefore suitable even for large-scale synthesis. Georg Thieme Verlag Stuttgart · New York.

Swern oxidation of bicyclo[2.2.1]hept-5-ene-2,3-diol and its pyrazine-fused derivatives: An improved synthesis of bicyclo[2.2.1]hept-5-ene-2,3-dione and an unexpected ring-opening reaction

An improved synthesis of bicyclo[2.2.1]hept-5-ene-2,3-dione by Swern oxidation of bicyclo[2.2.1]hept-5-ene-2,3-diol, and an unexpected ring-opening reaction by the Swern oxidation of pyrazine-fused congeners are described.

Phase Transitions in 5,6-dioxycarbonylbicyclohept-2-ene

The temperature dependence of phase structure in 5,6-dioxycarbonylbicyclohept-2-ene was investigated by DSC, X-ray diffraction, optical microscopy and 1H NMR.The existence of an endotherm in DSC, loss of optical anisotropy, formation of diffuse diffraction patterns and drastic changes in 1H NMR relaxations indicated the formation of a'plastic crystal' phase, well below the melting point.NMR relaxation rates were measured as a function of temperature.There are sharp changes in relaxation rates at the plastic crystal transition.The transition introduces rapid molecular rotation, wthout translation.T1H relaxations show a change in magnitude for the rate, but no change in relaxation mechanism.