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Chemical Compound Review

Norbornene     bicyclo[2.2.1]hept-2-ene

Synonyms: Norcamphene, Norfenchene, Norbornylene, N32407_ALDRICH, AG-K-75390, ...
 
 
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Disease relevance of Norcamphene

 

High impact information on Norcamphene

  • A norbornene-mediated palladium-catalyzed tandem alkylation/cyanation sequence is described in which an alkyl-aryl bond and a nitrile-aryl bond are formed in one pot [2].
  • Amphiphilic cationic polynorbornene derivatives, soluble in water, were prepared from modular norbornene monomers, with a wide range of molecular weights (M(n) = 1600-137 500 g/mol) and narrow polydispersities (PDI = 1.1-1.3) [3].
  • At norbornene/ethylene ratios larger than ca. 1, the catalysts mediated room-temperature living copolymerization of ethylene and norbornene to form high molecular weight monodisperse copolymers (M(n) > 500,000, M(w)/M(n) < 1.20) [4].
  • A series of norbornene-based resin beads were obtained by aqueous suspension ring-opening metathesis polymerization (ROMP) and used as polymeric supports for organic synthesis [5].
  • The key transformations are derived from diastereoselective intramolecular cyclization of aryllithiums and alpha-amidoalkylation reactions, with the ethylidene bridge of the norbornene moiety dictating the stereochemical outcome in both types of reactions [6].
 

Biological context of Norcamphene

  • Norbornene-constrained cyclic peptides with hairpin architecture: design, synthesis, conformation, and membrane ion transport [7].
  • The molecular structure of C(11)H(12)O(4), based on a norbornene core, was established to confirm the configuration of an acetoxy side-chain group in addition to the formation of the endo product [8].
 

Associations of Norcamphene with other chemical compounds

  • Hydrovinylation of norbornene. Ligand-dependent selectivity and asymmetric variations [9].
  • TSA 1 contains a bicyclo[2.2.1]heptene ring system that mimics the boat conformation of the Diels-Alder transition state and is designed to bind tightly to antibodies, nucleic acids, and imprinted polymers by means of hydrogen bonds and salt-bridges [10].
 

Gene context of Norcamphene

  • The conformational analysis of polynorbornene (PNB) chains was investigated with the AM1, MM2, AMBER and OPLS methods taking into consideration the possibility of binding of norbornene monomers to each other at various positions, i.e. exo-exo, exo-endo, endo-endo [11].
  • Studies toward the synthesis of azadirachtin, part 1: total synthesis of a fully functionalized ABC ring framework and coupling with a norbornene domain [12].
 

Analytical, diagnostic and therapeutic context of Norcamphene

  • X-ray crystallography revealed that the enantioselectivity arises from crystallization of the reactant in a conformation in which the carbonyl oxygen is more favorably oriented for bond formation to one end of the norbornene double bond than the other, thus leading to a predominance of a single enantiomer [13].
  • Evaluation of norbornene- beta-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis [14].

References

  1. Comparative acute toxicity and primary irritancy of the ethylidene and vinyl isomers of norbornene. Ballantyne, B., Myers, R.C., Klonne, D.R. Journal of applied toxicology : JAT. (1997) [Pubmed]
  2. Synthesis of Polycyclic Benzonitriles via a One-Pot Aryl Alkylation/Cyanation Reaction. Mariampillai, B., Alberico, D., Bidau, V., Lautens, M. J. Am. Chem. Soc. (2006) [Pubmed]
  3. Tuning the hemolytic and antibacterial activities of amphiphilic polynorbornene derivatives. Ilker, M.F., Nüsslein, K., Tew, G.N., Coughlin, E.B. J. Am. Chem. Soc. (2004) [Pubmed]
  4. Living copolymerization of ethylene with norbornene catalyzed by bis(pyrrolide-imine) titanium complexes with MAO. Yoshida, Y., Mohri, J., Ishii, S., Mitani, M., Saito, J., Matsui, S., Makio, H., Nakano, T., Tanaka, H., Onda, M., Yamamoto, Y., Mizuno, A., Fujita, T. J. Am. Chem. Soc. (2004) [Pubmed]
  5. Suspension ring-opening metathesis polymerization: the preparation of norbornene-based resins for application in organic synthesis. Lee, B.S., Mahajan, S., Clapham, B., Janda, K.D. J. Org. Chem. (2004) [Pubmed]
  6. Enantiodivergent synthesis of pyrrolo[2,1-a]isoquinolines based on diastereoselective Parham cyclization and alpha-amidoalkylation reactions. González-Temprano, I., Osante, I., Lete, E., Sotomayor, N. J. Org. Chem. (2004) [Pubmed]
  7. Norbornene-constrained cyclic peptides with hairpin architecture: design, synthesis, conformation, and membrane ion transport. Ranganathan, D., Haridas, V., Kurur, S., Nagaraj, R., Bikshapathy, E., Kunwar, A.C., Sarma, A.V., Vairamani, M. J. Org. Chem. (2000) [Pubmed]
  8. (5S)-3-oxo-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-5-yl acetate. Ellis, D.D., Spek, A.L. Acta crystallographica. Section C, Crystal structure communications. (2000) [Pubmed]
  9. Hydrovinylation of norbornene. Ligand-dependent selectivity and asymmetric variations. Kumareswaran, R., Nandi, M., RajanBabu, T.V. Org. Lett. (2003) [Pubmed]
  10. Design and synthesis of a transition state analogue for the Diels-Alder reaction. Arora, P.S., Van, Q.N., Famulok, M., Shaka, A.J., Nowick, J.S. Bioorg. Med. Chem. (1998) [Pubmed]
  11. A molecular mechanics and semiempirical molecular orbital study on the conformation of polynorbornene chains. Yilmaz, S.S., Abbasoğlu, R., Hazer, B. Journal of molecular modeling (Online) (2003) [Pubmed]
  12. Studies toward the synthesis of azadirachtin, part 1: total synthesis of a fully functionalized ABC ring framework and coupling with a norbornene domain. Nicolaou, K.C., Sasmal, P.K., Roecker, A.J., Sun, X.W., Mandal, S., Converso, A. Angew. Chem. Int. Ed. Engl. (2005) [Pubmed]
  13. Asymmetric synthesis of dihydrofurans via a formal retro-Claisen photorearrangement. Xia, W., Yang, C., Patrick, B.O., Scheffer, J.R., Scott, C. J. Am. Chem. Soc. (2005) [Pubmed]
  14. Evaluation of norbornene- beta-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis. Eder, K., Sinner, F., Mupa, M., Huber, C.G., Buchmeiser, M.R. Electrophoresis (2001) [Pubmed]
 
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