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维基百科

苊烯

十二月 13, 2023

苊烯（Acenaphthylene）又称萘并乙烯、1,8-亚乙基萘。是一种含有萘环并通过乙烯桥连萘环1位和8位的多环芳烃类有机化合物。它是煤焦油的成分之一，通过氢化还原分子中的乙烯结构能得到苊。不同于其他大多数多环芳烃化合物，苊烯不发出荧光。

苊烯
IUPAC名
苊烯
识别
CAS号 208-96-8  Y
PubChem 9161
ChemSpider 8807
SMILES
 
  • c1cc2cccc3/C=C\c(c1)c23
InChI
 
  • 1/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
InChIKey HXGDTGSAIMULJN-UHFFFAOYAQ
ChEBI 33081
性质
化学式 C12H8
摩尔质量 152.192 g·mol⁻¹
外观 白色结晶状粉末
密度 固体
熔点 90-92 ℃
沸点 280 ℃
溶解性（水） 不可溶
溶解性（乙醇） 易溶
溶解性（乙醚） 易溶
溶解性（苯） 易溶
溶解性（氯仿） 可溶
危险性
警示术语 R：R22-R36/37/38
安全术语 S：S26-S36-S37-S39
MSDS MSDS
闪点 ?℃
相关物质
相关化学品 苊
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

化学性质及反应 编辑

苊烯分子五元环上的烯烃双键虽然处于环内且与萘环共轭但性质较为活泼，所以涉及苊烯的化学反应主要发生在苊烯五元环上的烯烃双键上。苊烯能被一些烷基金属试剂或碱金属比如单质锂反应，发生去质子化形成苊烯基负离子[1]，能发生溴代[2]、卤素或水的加成反应[3][4][5][6][7][8]、环氧化反应、氮杂环丙烷化、氢甲酰化反应[9]、Heck反应[10]、碳碳双键的氧化断裂[11]、还原[12][13]、硝化[14]、双羟基化[15][16]、D-A反应[17][18]、[2+2]环加成[19][20]、1,3-偶极环加成反应[21]、硼烷对苊烯的加成[22]、与芳基酰氯的脱羰基偶联[23]等多种反应。

1-溴代苊烯可由苊烯先经三溴化吡啶鎓的加成，后在碱存在下发生消除反应制得[24]

参考文献 编辑

  1. ^ Lillo, Victor J.; Gomez, Cecilia; Yus, Miguel. DTBB-Catalysed Lithiation of Acenaphthylene and Reaction with Carbonyl Compounds. Synthesis. 2008, (8): 1241–1248. doi:10.1055/s-2008-1042943. 
  2. ^ Eguchi, Hisao; Kawaguchi, Hideichiro; Yoshinaga, Sachiyo; Nishida, Akiko; Nishiguchi, Takeshi; Fujisaki, Shizuo. Halogenation Using N-Halogenocompounds. II. Acid Catalyzed Bromination of Aromatic Compounds with 1,3-Dibromo-5,5-dimethylhydantoin. Bulletin of the Chemical Society of Japan. 1994, 67 (7): 1918–1921. doi:10.1246/bcsj.67.1918. 
  3. ^ Stanley J. Cristol , Frank R. Stermitz , Patricia S. Ramey. Mechanisms of Elimination Reactions. XVII. The cis- and trans-1,2-Dichloroacenaphthenes; trans-1,2-Dibromoacenaphthene. J. Am. Chem. Soc. 1956, 78 (19): 4939–4941. doi:10.1021/ja01600a034. 
  4. ^ Boris Šket and Marko Zupan. Fluorination with xenon difluoride. Part 15. Stereochemistry of fluorine addition to acenaphthylene and dihydronaphthalenes. J. Chem. Soc., Perkin Trans. 1. 1977: 2169–2172. doi:10.1039/P19770002169. 
  5. ^ Nakayama, Juzo; Ohshima, Etsuo; Ishii, Akihiko; Hoshino, Masamatsu. Ramberg-Backlund reaction of 1,3-dibromo-1H,3H-naphtho[1,8-cd]thiopyran 2,2-dioxide. Formation of acenaphthyne intermediate.. J.Org. Chem. 1983, 48 (1): 60–65. doi:10.1021/jo00149a013. 
  6. ^ Ma, Kefeng; Weiss, Richard G.; Li, Shaw. Stereoselective Bromination Reactions Using Tridecylmethylphosphonium Tribromide in a “Stacked” Reactor. Org. Lett. 2008, 10 (19): 4155 – 4158. doi:10.1021/ol801327n. 
  7. ^ Broadus, Katherine M.; Kass, Steven R. The Electron as a Protecting Group. 3. Generation of Acenaphthyne Radical Anion and the Determination of the Heat of Formation of a Strained Cycloalkyne. J. Am. Chem. Soc. 2001, 123 (18): 4189 – 4196. doi:10.1021/ja003069f. 
  8. ^ Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Eissen, Marco; Fleckenstein, Jens. Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst. Green Chem. 2009, 11 (1): 120 – 126. doi:10.1039/b814989e. 
  9. ^ Raffaelli, Andrea; Rosini, Carlo; Dini, Massimo; Salvadori, Piero. A Simple Route to Racemic Acenaphthene-1-carboxylic Acid via Hydroformylation of Acenaphthylene. Synthesis. 1988, (11): 893 – 894. doi:10.1055/s-1988-27742. 
  10. ^ Dyker, Gerald; Merz, Klaus; Oppel, Iris M.; Muth, Enrico. Palladium-Catalyzed Naphthylation of Acenaphthylene. Synlett. 2007, (6): 897 – 900. doi:10.1055/s-2007-970785. 
  11. ^ Gao, J.; Ma, S. L.; Liao, D. Z. Polish Journal of Chemistry. 1998, 72 (5): 839 – 843.  缺少或|title=为空 (帮助)
  12. ^ Tsukinoki, Takehito; Kanda, Tadashige; Liu, Guo-Bin; Tsuzuki, Hirohisa; Tashiro, Masashi. Organic reaction in water. Part 3:1 A facile method for reduction of aromatic rings using a raney Ni–Al alloy in dilute aqueous alkaline solution under mild conditions. Tetrahedron Lett. 2000volume=41, (31): 5865 – 5868. doi:10.1016/S0040-4039(00)00636-5. 
  13. ^ Fry, Albert J.; Allukian, Myron; Williams, Allison D. Reduction of diaryl alkenes by hypophosphorous acid–iodine in acetic acid. Tetrahedron. 2002, 58 (22): 4411 – 4416. doi:10.1016/S0040-4020(02)00415-5. 
  14. ^ Cantrell,T.S.; Shechter,H. Reactions of dinitrogen tetroxide with acenaphthylene. Diels-Alder reactions and photodimerization of 1-nitro- and 1,2-dinitroacenaphthylenes. J. Org. Chemistry. 1968, 33: 114 – 118. doi:10.1021/jo01265a020. 
  15. ^ F. D. Gunstone and L. J. Morris. 88. Fatty acids. Part V. Applications of the Woodward cis-hydroxylation procedure to long-chain olefinic compounds. J. Chem. Soc. 1957: 487–489. doi:10.1039/JR9570000487. 
  16. ^ Stability of boronic esters – Structural effects on the relative rates of transesterification of 2-(phenyl)-1,3,2-dioxaborolane. J. Organomet. Chem. 2007, 692 (4): 784 – 790. doi:10.1016/j.jorganchem.2006.10.013.  缺少或|title=为空 (帮助)
  17. ^ Raasch, Maynard S. Annulations with tetrachlorothiophene 1,1-dioxide. J. Org. Chem. 1980, 45 (5): 856 – 867. doi:10.1021/jo01293a019. 
  18. ^ Branchi, Barbara; Balzani, Vincenzo; Ceroni, Paola; Kuchenbrandt, Mireia Campana; Klaerner, Frank-Gerrit; Blaeser, Dieter; Boese, Roland. Molecular Clips with Extended Aromatic Sidewalls as Receptors for Electron-Acceptor Molecules. Synthesis and NMR, Photophysical, and Electrochemical Properties. J. Org. Chem. 2008, 73 (15): 5839 – 5851. doi:10.1021/jo8007513. 
  19. ^ Treutwein, Jonas; Hilt, Gerhard. Cobalt-Catalyzed [2+2] Cycloaddition. Angewandte Chemie, International Edition. 2008, 47 (36): 6811–6813. doi:10.1002/anie.200801778. 
  20. ^ Yoshizawa, Michito; Takeyama, Yoshihisa; Kusukawa, Takahiro; Fujita, Makoto. Cavity-Directed, Highly Stereoselective [2+2] Photodimerization of Olefins within Self-Assembled Coordination Cages. Angewandte Chemie International Edition. 2002-04-16, 41 (8): 1347–1349 [2023-03-24]. doi:10.1002/1521-3773(20020415)41:8<1347::AID-ANIE1347>3.0.CO;2-X. （原始内容于2023-03-24）. 
  21. ^ Heinrich Wamhoff, Magdy Zahran. Dihalogentriphenylphosphoranes in Heterocyclic Synthesis; 15.1 A Simple One-Pot-Procedure for the Generation of Nitrilimines with the Aid of Dihalogentriphenyl-phosphoranes: 1,3-Dipolar Cycloadditions and 1,5-Electrocyclizations. Synthesis. 1987, (10): 876–879. doi:10.1055/s-1987-28108. 
  22. ^ Fernandez, Elena; Maeda, Kenji; Hooper, Mark W.; Brown, John M. Chemistry--A European Journal. 2000, 6 (10): 1840–1846.  缺少或|title=为空 (帮助)
  23. ^ Toru Sugihara, Tetsuya Satoh, Masahiro Miura, Masakatsu Nomura. Rhodium-Catalyzed Coupling Reaction of Aroyl Chlorides with Alkenes. Adv. Synth. Catal. 2004, 346: 1765–1772. doi:10.1002/adsc.200404145. 
  24. ^ Katherine M. Broadus and Steven R. Kass. The Electron as a Protecting Group. 3. Generation of Acenaphthyne Radical Anion and the Determination of the Heat of Formation of a Strained Cycloalkyne. J. Am. Chem. Soc. 2001, 123 (18): 4189–4196. doi:10.1021/ja003069f. 

参见 编辑

十二月 13, 2023
苊烯, 此條目需要擴充, 2012年8月25日, 请協助改善这篇條目, 更進一步的信息可能會在討論頁或扩充请求中找到, 请在擴充條目後將此模板移除, acenaphthylene, 又称萘并乙烯, 亚乙基萘, 是一种含有萘环并通过乙烯桥连萘环1位和8位的多环芳烃类有机化合物, 它是煤焦油的成分之一, 通过氢化还原分子中的乙烯结构能得到苊, 不同于其他大多数多环芳烃化合物, 不发出荧光, iupac名识别cas号, ypubchem, 9161chemspider, 8807smiles, c1cc2cccc3, c. 此條目需要擴充 2012年8月25日 请協助改善这篇條目 更進一步的信息可能會在討論頁或扩充请求中找到 请在擴充條目後將此模板移除 苊烯 Acenaphthylene 又称萘并乙烯 1 8 亚乙基萘 是一种含有萘环并通过乙烯桥连萘环1位和8位的多环芳烃类有机化合物 它是煤焦油的成分之一 通过氢化还原分子中的乙烯结构能得到苊 不同于其他大多数多环芳烃化合物 苊烯不发出荧光 苊烯IUPAC名苊烯识别CAS号 208 96 8 YPubChem 9161ChemSpider 8807SMILES c1cc2cccc3 C C c c1 c23InChI 1 C12H8 c1 3 9 4 2 6 11 8 7 10 5 1 12 9 11 h1 8HInChIKey HXGDTGSAIMULJN UHFFFAOYAQChEBI 33081性质化学式 C12H8摩尔质量 152 192 g mol 外观 白色结晶状粉末密度 固体熔点 90 92 沸点 280 溶解性 水 不可溶溶解性 乙醇 易溶溶解性 乙醚 易溶溶解性 苯 易溶溶解性 氯仿 可溶危险性警示术语 R R22 R36 37 38安全术语 S S26 S36 S37 S39MSDS MSDS闪点 相关物质相关化学品 苊若非注明 所有数据均出自标准状态 25 100 kPa 下 化学性质及反应 编辑苊烯分子五元环上的烯烃双键虽然处于环内且与萘环共轭但性质较为活泼 所以涉及苊烯的化学反应主要发生在苊烯五元环上的烯烃双键上 苊烯能被一些烷基金属试剂或碱金属比如单质锂反应 发生去质子化形成苊烯基负离子 1 能发生溴代 2 卤素或水的加成反应 3 4 5 6 7 8 环氧化反应 氮杂环丙烷化 氢甲酰化反应 9 Heck反应 10 碳碳双键的氧化断裂 11 还原 12 13 硝化 14 双羟基化 15 16 D A反应 17 18 2 2 环加成 19 20 1 3 偶极环加成反应 21 硼烷对苊烯的加成 22 与芳基酰氯的脱羰基偶联 23 等多种反应 1 溴代苊烯可由苊烯先经三溴化吡啶鎓的加成 后在碱存在下发生消除反应制得 24 参考文献 编辑 Lillo Victor J Gomez Cecilia Yus Miguel DTBB Catalysed Lithiation of Acenaphthylene and Reaction with Carbonyl Compounds Synthesis 2008 8 1241 1248 doi 10 1055 s 2008 1042943 Eguchi Hisao Kawaguchi Hideichiro Yoshinaga Sachiyo Nishida Akiko Nishiguchi Takeshi Fujisaki Shizuo Halogenation Using N Halogenocompounds II Acid Catalyzed Bromination of Aromatic Compounds with 1 3 Dibromo 5 5 dimethylhydantoin Bulletin of the Chemical Society of Japan 1994 67 7 1918 1921 doi 10 1246 bcsj 67 1918 Stanley J Cristol Frank R Stermitz Patricia S Ramey Mechanisms of Elimination Reactions XVII The cis and trans 1 2 Dichloroacenaphthenes trans 1 2 Dibromoacenaphthene J Am Chem Soc 1956 78 19 4939 4941 doi 10 1021 ja01600a034 Boris Sket and Marko Zupan Fluorination with xenon difluoride Part 15 Stereochemistry of fluorine addition to acenaphthylene and dihydronaphthalenes J Chem Soc Perkin Trans 1 1977 2169 2172 doi 10 1039 P19770002169 Nakayama Juzo Ohshima Etsuo Ishii Akihiko Hoshino Masamatsu Ramberg Backlund reaction of 1 3 dibromo 1H 3H naphtho 1 8 cd thiopyran 2 2 dioxide Formation of acenaphthyne intermediate J Org Chem 1983 48 1 60 65 doi 10 1021 jo00149a013 Ma Kefeng Weiss Richard G Li Shaw Stereoselective Bromination Reactions Using Tridecylmethylphosphonium Tribromide in a Stacked Reactor Org Lett 2008 10 19 4155 4158 doi 10 1021 ol801327n Broadus Katherine M Kass Steven R The Electron as a Protecting Group 3 Generation of Acenaphthyne Radical Anion and the Determination of the Heat of Formation of a Strained Cycloalkyne J Am Chem Soc 2001 123 18 4189 4196 doi 10 1021 ja003069f Podgorsek Ajda Stavber Stojan Zupan Marko Iskra Jernej Eissen Marco Fleckenstein Jens Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst Green Chem 2009 11 1 120 126 doi 10 1039 b814989e Raffaelli Andrea Rosini Carlo Dini Massimo Salvadori Piero A Simple Route to Racemic Acenaphthene 1 carboxylic Acid via Hydroformylation of Acenaphthylene Synthesis 1988 11 893 894 doi 10 1055 s 1988 27742 Dyker Gerald Merz Klaus Oppel Iris M Muth Enrico Palladium Catalyzed Naphthylation of Acenaphthylene Synlett 2007 6 897 900 doi 10 1055 s 2007 970785 Gao J Ma S L Liao D Z Polish Journal of Chemistry 1998 72 5 839 843 缺少或 title 为空 帮助 Tsukinoki Takehito Kanda Tadashige Liu Guo Bin Tsuzuki Hirohisa Tashiro Masashi Organic reaction in water Part 3 1 A facile method for reduction of aromatic rings using a raney Ni Al alloy in dilute aqueous alkaline solution under mild conditions Tetrahedron Lett 2000volume 41 31 5865 5868 doi 10 1016 S0040 4039 00 00636 5 请检查 date 中的日期值 帮助 Fry Albert J Allukian Myron Williams Allison D Reduction of diaryl alkenes by hypophosphorous acid iodine in acetic acid Tetrahedron 2002 58 22 4411 4416 doi 10 1016 S0040 4020 02 00415 5 Cantrell T S Shechter H Reactions of dinitrogen tetroxide with acenaphthylene Diels Alder reactions and photodimerization of 1 nitro and 1 2 dinitroacenaphthylenes J Org Chemistry 1968 33 114 118 doi 10 1021 jo01265a020 F D Gunstone and L J Morris 88 Fatty acids Part V Applications of the Woodward cis hydroxylation procedure to long chain olefinic compounds J Chem Soc 1957 487 489 doi 10 1039 JR9570000487 Stability of boronic esters Structural effects on the relative rates of transesterification of 2 phenyl 1 3 2 dioxaborolane J Organomet Chem 2007 692 4 784 790 doi 10 1016 j jorganchem 2006 10 013 缺少或 title 为空 帮助 Raasch Maynard S Annulations with tetrachlorothiophene 1 1 dioxide J Org Chem 1980 45 5 856 867 doi 10 1021 jo01293a019 Branchi Barbara Balzani Vincenzo Ceroni Paola Kuchenbrandt Mireia Campana Klaerner Frank Gerrit Blaeser Dieter Boese Roland Molecular Clips with Extended Aromatic Sidewalls as Receptors for Electron Acceptor Molecules Synthesis and NMR Photophysical and Electrochemical Properties J Org Chem 2008 73 15 5839 5851 doi 10 1021 jo8007513 Treutwein Jonas Hilt Gerhard Cobalt Catalyzed 2 2 Cycloaddition Angewandte Chemie International Edition 2008 47 36 6811 6813 doi 10 1002 anie 200801778 Yoshizawa Michito Takeyama Yoshihisa Kusukawa Takahiro Fujita Makoto Cavity Directed Highly Stereoselective 2 2 Photodimerization of Olefins within Self Assembled Coordination Cages Angewandte Chemie International Edition 2002 04 16 41 8 1347 1349 2023 03 24 doi 10 1002 1521 3773 20020415 41 8 lt 1347 AID ANIE1347 gt 3 0 CO 2 X 原始内容存档于2023 03 24 Heinrich Wamhoff Magdy Zahran Dihalogentriphenylphosphoranes in Heterocyclic Synthesis 15 1 A Simple One Pot Procedure for the Generation of Nitrilimines with the Aid of Dihalogentriphenyl phosphoranes 1 3 Dipolar Cycloadditions and 1 5 Electrocyclizations Synthesis 1987 10 876 879 doi 10 1055 s 1987 28108 Fernandez Elena Maeda Kenji Hooper Mark W Brown John M Chemistry A European Journal 2000 6 10 1840 1846 缺少或 title 为空 帮助 Toru Sugihara Tetsuya Satoh Masahiro Miura Masakatsu Nomura Rhodium Catalyzed Coupling Reaction of Aroyl Chlorides with Alkenes Adv Synth Catal 2004 346 1765 1772 doi 10 1002 adsc 200404145 Katherine M Broadus and Steven R Kass The Electron as a Protecting Group 3 Generation of Acenaphthyne Radical Anion and the Determination of the Heat of Formation of a Strained Cycloalkyne J Am Chem Soc 2001 123 18 4189 4196 doi 10 1021 ja003069f 参见 编辑苊 苊醌 取自 https zh wikipedia org w index php title 苊烯 amp oldid 79106703, 维基百科，wiki，书籍，书籍，图书馆，

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