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Nitroalken

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Nitroalken yoki nitro olefin, uning tarkibiy qismlari, alken va nitroguruhlarning funksionalligini birlashtirgan funktsional guruh boʻlib, alkenlarni faollashtirish orqali oʻzining kimyoviy xususiyatlarini namoyon qiladi va funktsional guruhni Maykl reaktsiyasi yoki Diels-Alder qo'shimchalari kabi maxsus reaktsiyalarda foydali qiladi.

Sintez

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Nitroalkenlar turli yoʻllar bilan sintezlanadi, diqqatga sazovor misollar:

  • Kumush nitrit va elementar yoddan in-situ hosil boʻlgan nitril yodid bilan alkenni nitrlash :[5]
  • Alkenlarni Clayfen bilan toʻgʻridan-toʻgʻri nitrlash ( Montmorillonit loyida qoʻllab-quvvatlanadigan temir (III) nitrat ):[7]
  • Nitro-spirtlarning suvsizlanishi:[8]

Reaksiyalar

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Nitroalkenlar turli xil kimyoviy funktsiyalar uchun foydali vositadir.

  • Likoritsidin sintezida oʻzini Maykl akseptori sifatida tutadigan nitroalken:[1][9]
  • Barton-Zard reaksiyasi orqali pirol hosilalarining sintezi:[11]
  • Nitroalkenning indol hosil qiluvchi peritsiklik reaksiyasi :[12]
  • Asimmetrik Stetter reaktsiyasi :[15]

Manbalar

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  1. ↑ 1,0 1,1 1,2 Furniss, Brian. Vogel's Textbook of Practical Organic Chemistry 5th Ed.. London: Longman Science & Technical, 1996 — 635, 768, 1035–1036, & 1121-bet. 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. 
  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. 
  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. Heterocyclic Chemistry in Drug Discovery. New York: Wiley, 2013. ISBN 9781118354421.  pp.43-4
  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. https://archive.org/details/sim_synthesis_1999-05_5/page/793. 
  13. ↑ 13,0 13,1 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. https://archive.org/details/sim_bulletin-of-the-chemical-society-of-japan_1990-04_63_4/page/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. 
  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. PMID 19722669. PMC 2747345. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2747345.  
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