デンドラレン
出典: フリー百科事典『ウィキペディア（Wikipedia）』 (2017/03/27 01:31 UTC 版)
デンドラレン (dendralene) は交差共役構造を持った非環式ポリエンである[1][2][3]。最も単純なデンドラレンは1,3-ブタジエン (1) （[2]デンドラレン）であり、以降は[3]デンドラレン (2)、[4]デンドラレン (3)、[5]デンドラレン (4) と続く。ブタジエンは交差共役構造を持たない唯一のデンドラレンである。
- ^ Henning Hopf, Classics in Hydrocarbon Chemistry, Wiley VCH, 2000.
- ^ Hopf, H.; Sherburn, M. S. (2012). “Dendralenes Branch Out: Cross-Conjugated Oligoenes Allow the Rapid Generation of Molecular Complexity”. Angew. Chem. Int. Ed. 51: 2298–2338. doi:10.1002/anie.201102987.
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- ^ Blomquist, A. T.; Verdol, Joseph A. (1955). “2-Vinyl-1,3-butadiene”. J. Am. Chem. Soc. 77 (1): 81–83. doi:10.1021/ja01606a025.
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- ^ Singh, R.; Ghosh, S. K. (2011). “Synthesis of substituted [3]dendralenes and their unique cycloaddition reactions”. Chem. Commun. 47 (38): 10809-10811. doi:10.1039/C1CC14211A. PMID 21874204.
- ^ Bradford, T. A.; Payne, A. D.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. (2007). “Cross-Coupling for Cross-Conjugation:? Practical Synthesis and Diels?Alder Reactions of [3]Dendralenes”. Org. Lett. 9 (23): 4861–4864. doi:10.1021/ol7021998.
- ^ Beydoun K, Zhang HJ, Sundararaju B, Demerseman B, Achard M, Xi Z, Bruneau C (2009). “Efficient ruthenium-catalyzed synthesis of [3]dendralenes from 1,3-dienic allylic carbonates”. Chem. Commun. (43): 6580-6582. doi:10.1039/B913595B. PMID 19865656.
- ^ a b c Payne, A. D.; Willis, A. C.; Sherburn, M. S. (2005). “Practical Synthesis and Diels−Alder Chemistry of [4]Dendralene”. J. Am. Chem. Soc. 127 (35): 12188–12189. doi:10.1021/ja053772+. ISSN 0002-7863. PMID 16131173.
- ^ Brain, P. T.; Smart, B. A.; Robertson, H. E.; Davis,M. J.; Rankin, D. W. H.; Henry, W. J.; Gosney, I. (1997). “Molecular Structure of 3,4-Dimethylenehexa-1,5-diene ([4]Dendralene), C8H10, in the Gas Phase As Determined by Electron Diffraction and ab Initio Calculations”. J. Org. Chem. 62 (9): 2767-2773. doi:10.1021/jo962091h.
- ^ Payne AD, Bojase G, Paddon-Row MN, Sherburn MS (2009). “Practical Synthesis of the Dendralene Family Reveals Alternation in Behavior”. Angew. Chem. Int. Ed. 48 (26): 4836-4839. doi:10.1002/anie.200901733. PMID 19455528.
- ^ Saglam MF, Fallon T, Paddon-Row MN, Sherburn MS (2016). “Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes”. J. Am. Chem. Soc. 138 (3): 1022-1032. doi:10.1021/jacs.5b11889. PMID 26721640.
- ^ Brummond, Kay M.; You, Lingfeng (2005). “Consecutive Rh(I)-catalyzed Alder-ene/Diels–Alder/Diels–Alder reaction sequence affording rapid entry to polycyclic compounds”. Tetrahedron 61 (26): 6180–6185. doi:10.1016/j.tet.2005.03.141.
- ^ Hopf, H.; Yildizhan, Ş. (2011). “Highly Functionalized, Angularly Anellated Aromatic Compounds from Dendralenes”. Eur. J. Org. Chem. 2011: 2029–2034. doi:10.1002/ejoc.201001536.
- ^ Kobayashi, S.; Furuya, T.; Otani, T.; Saito, T. (2008). “A novel and facile stereocontrolled synthetic method for polyhydro-quinolines and pyridopyridazines via a diene-transmissive Diels–Alder reaction involving inverse electron-demand hetero Diels–Alder cycloaddition of cross-conjugated azatrienes”. Tetrahedron 64 (41): 9705-9716. doi:10.1016/j.tet.2008.07.102.
- ^ Pronin, S. V.; Shenvi, R. A. (2012). “Synthesis of a Potent Antimalarial Amphilectene”. J. Am. Chem. Soc. 134 (48): 19604-19606. doi:10.1021/ja310129b. PMID 23153381.
- ^ Green, N. J.; Lawrence, A. L.; Bojase, G.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. (2013). “Domino Cycloaddition Organocascades of Dendralenes”. Angew. Chem. Int. Ed. 52: 8333–8336. doi:10.1002/anie.201302185.
- ^ Bradford, T. A.; Payne, A. D.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. (2010). “Practical Synthesis and Reactivity of [3]Dendralene”. J. Org. Chem. 75 (2): 491-494. doi:10.1021/jo9024557.
- ^ Tan, S. M.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. (2016). “Multicomponent Diene-Transmissive Diels–Alder Sequences Featuring Aminodendralenes”. Angew. Chem. Int. Ed. 55 (9): 3081-3085. doi:10.1002/anie.201510925. PMID 26823233.
- ^ Saglam, M. F.; Alborzi, A. R.; Payne, A. D.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. (2016). “Synthesis and Diels–Alder Reactivity of Substituted [4]Dendralenes”. J. Org. Chem. 81 (4): 1461-1475.
- ^ Bojase, G.; Nguyen, T. V.; Payne, A. D.; Willis, A. C.; Sherburn, M. S. (2011). “Synthesis and properties of the ivyanes: the parent 1,1-oligocyclopropanes”. Chem. Sci. 2: 229–232. doi:10.1039/C0SC00500B.
- ^ Okada, K.; Maehara, K.; Oda, M. (1994). “A novel photochemical reaction of [3]dendralene derivatives”. Tetrahedron Lett. 35 (29): 5251–5252. doi:10.1016/S0040-4039(00)77076-6.
- ^ Kosai, T.; Ishida, S.; Iwamoto, T. (2015). “Transformation of azulenes to bicyclic [4]dendralene and heptafulvene derivatives via photochemical cycloaddition of dialkylsilylene”. Chem. Commun. 51: 10707-10709. doi:10.1039/C5CC03424H. PMID 26050797.
[続きの解説]
「デンドラレン」の続きの解説一覧
- 1 デンドラレンとは
- 2 デンドラレンの概要
- デンドラレンのページへのリンク
