니트로알켄

Nitroalkene

니트로알켄(nitroalkene) 또는 니트로올레핀(nitro olefin)은 알켄 활성화를 통해 자신의 화학적 성질을 나타내면서 구성 부품인 알켄과 니트로 그룹의 기능을 결합한 기능 그룹으로, 마이클 반응이나 디엘-알데르 첨가 등 특수 반응에 유용한 기능 그룹이다.[1]

합성

니트로알카네는 다양한 방법으로 합성되는데, 주목할 만한 예는 다음과 같다.

Furfural nitroaldol condensation.png
Nitrogenation of a phenylisopropene.png
Direct nitration of styrene with alumina catalyst.svg
Direct nitration of styrene using FeNO3 on a Clayfen support.png
  • 질산 알코올의 탈수:[8]
Dehydration of 2-nitroethanol to nitroethylene via phthalic anhydride.svg

반응

니트로알카네는 다양한 화학적 기능성에 유용한 매개체다.

Michael acceptor intermediate in Lycoricidine Synthesis.svg
Nitroalkene dienophile in cycloaddition with butadiene.svg
Barton-Zard reaction.svg
Pericyclic reaction of a nitroalkene yielding an indole.svg
Partial hydrogenation of a nitrostyrene to an alkene hydroxylamine.svg
Hydrogenation of a nitrostyrene to a primary amine.svg
Asymmetric Stetter Reaction with Nitroalkenes.png

참조

  1. ^ a b c d Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. pp. 635, 768, 1035–1036, & 1121. ISBN 9780582462366.
  2. ^ Ballini, Roberto; Castagnani, Roberto; Petrini, Marino (1992). "Chemoselective synthesis of functionalized conjugated nitroalkenes". The Journal of Organic Chemistry. 57 (7): 2160–2162. doi:10.1021/jo00033a045.
  3. ^ Worrall, David E. (1929). "Nitrostyrene". Org. Synth. 9: 66. doi:10.15227/orgsyn.009.0066.
  4. ^ Chandrasekhar, S.; Shrinidhi, A. (2014). "Useful Extensions of the Henry Reaction: Expeditious Routes to Nitroalkanes and Nitroalkenes in Aqueous Media". Synthetic Communications. 44 (20): 3008–3018. doi:10.1080/00397911.2014.926373. S2CID 98439096.
  5. ^ Waldman, Steve; Monte, Aaron, Monte; Bracey, Ann & Nichols, David (1996). "One-pot Claisen rearrangement/O-methylation/alkene isomerization in the synthesis of ortho-methoxylated phenylisopropylamines". Tetrahedron Letters. 37 (44): 7889–7892. doi:10.1016/0040-4039(96)01807-2.{{cite journal}}: CS1 maint : 복수이름 : 작성자 목록(링크)
  6. ^ Mukaiyama, T.; Hata E. & Yamada, T. (1995). "Convenient and Simple Preparation of Nitroolefins Nitration of Olefins with Nitric Oxide". Chemistry Letters. 24 (7): 505–506. doi:10.1246/cl.1995.505.
  7. ^ Varma, Rajender; Naicker, Kannan; Liesen, Per (1998). "Selective nitration of styrenes with clayfen and clayan: A solvent-free synthesis of β-nitrostyrenes". Tetrahedron Letters. 39 (23): 3977–3980. doi:10.1016/S0040-4039(98)00740-0.
  8. ^ Ranganathan, Darshan; Rao, Bhushan; Ranganathan, Subramania; Mehrotra, Ashok & Iyengar, Radha (1980). "Nitroethylene: a stable, clean, and reactive agent for organic synthesis". The Journal of Organic Chemistry. 45 (7): 1185–1189. doi:10.1021/jo01295a003.
  9. ^ Jubert, Carole & Knochel, Paul (1992). "Preparation of polyfunctional nitro olefins and nitroalkanes using the copper-zinc reagents RCu(CN)ZnI". The Journal of Organic Chemistry. 57 (20): 5431–5438. doi:10.1021/jo00046a027.
  10. ^ Noboru Ono; Hideyoshi Miyake; Akio Kamimura & Aritsune, Kaji (1987). "Regioselective Diels–Alder reactions. The nitro group as a regiochemical control element". Perkin Transactions. 1: 1929–1935. doi:10.1039/P19870001929.
  11. ^ Jie Jack Li (2013). Heterocyclic Chemistry in Drug Discovery. New York: Wiley. ISBN 9781118354421. 43-4 페이지
  12. ^ Novellino, Luisa; d'Ischia, Marco & Prota, Giuseppe (1999). "Expedient Synthesis of 5,6-Dihydroxyindole and Derivatives via an Improved Zn(II)-Assisted 2,β-Dinitrostyrene Approach". Synthesis. 1999 (5): 793–796. doi:10.1055/s-1999-3469.
  13. ^ a b Masahiko Kohno; Shigehiro Sasao & Shun-Ichi Murahashi (1990). "Synthesis of Phenethylamines by Hydrogenation of β-Nitrostyrenes". Bulletin of the Chemical Society of Japan. 63 (4): 1252–1254. doi:10.1246/bcsj.63.1252.
  14. ^ Koch, Werner & Reichert, Benno (1935). "Über die katalytische Hydrierung substituierter ω-Nitrostyrole". Archiv der Pharmazie. 273 (18–20): 265–274. doi:10.1002/ardp.19352731802. S2CID 95731916.
  15. ^ DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. (2009). "Catalytic Asymmetric Intermolecular Stetter Reaction of Heterocyclic Aldehydes with Nitroalkenes: Backbone Fluorination Improves Selectivity". Journal of the American Chemical Society. 131 (31): 10872–10874. doi:10.1021/ja904375q. PMC 2747345. PMID 19722669.