苊

苊
	IUPAC名; 苊
别名	苊烯
识别
CAS号	208-96-8
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	1,2-二氢苊
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

苊^[1]（英语：Acenaphthylene）也常作苊烯，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。

Quick Facts 苊, 识别 ...

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化学性质及反应

苊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五元环上的烯烃双键上。苊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负离子^[2]，能发生溴代^[3]、卤素或水的加成反应^[4]^[5]^[6]^[7]^[8]^[9]、环氧化反应、氮杂环丙烷化、氢甲酰化反应^[10]、Heck反应^[11]、碳碳双键的氧化断裂^[12]、还原^[13]^[14]、硝化^[15]、双羟基化^[16]^[17]、D-A反应^[18]^[19]、[2+2]环加成^[20]^[21]、1,3-偶极环加成反应^[22]、硼烷对苊的加成^[23]、与芳基酰氯的脱羰基偶联^[24]等多种反应。

1-溴苊可由苊先经三溴化吡啶𬭩的加成，后在碱存在下发生消除反应制得。^[25]

另见

参考文献

[1]
中国化学会有机化合物命名审定委员会. 有机化合物命名原则 2017. 科学出版社. pp 69. ISBN 978-7-03-055295-2
[2]
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.
[3]
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.
[4]
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.
[5]
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.
[6]
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.
[7]
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.
[8]
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.
[9]
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.
[10]
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.
[11]
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.
[12]
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)
[13]
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. 2000, 41 (31): 5865 – 5868. doi:10.1016/S0040-4039(00)00636-5.
[14]
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.
[15]
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.
[16]
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.
[17]
Roy, Chandra D.; Brown, Herbert C. 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.
[18]
Raasch, Maynard S. Annulations with tetrachlorothiophene 1,1-dioxide. J. Org. Chem. 1980, 45 (5): 856 – 867. doi:10.1021/jo01293a019.
[19]
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.
[20]
Treutwein, Jonas; Hilt, Gerhard. Cobalt-Catalyzed [2+2] Cycloaddition. Angewandte Chemie, International Edition. 2008, 47 (36): 6811–6813. doi:10.1002/anie.200801778.
[21]
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. （原始内容存档于2023-03-24）.
[22]
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.
[23]
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)
[24]
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.
[25]
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.

[1] [1]
中国化学会有机化合物命名审定委员会. 有机化合物命名原则 2017. 科学出版社. pp 69. ISBN 978-7-03-055295-2

[2] [2]
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.

[3] [3]
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.

[4] [4]
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.

[5] [5]
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.

[6] [6]
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.

[7] [7]
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.

[8] [8]
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.

[9] [9]
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.

[10] [10]
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.

[11] [11]
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.

[12] [12]
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)

[13] [13]
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. 2000, 41 (31): 5865 – 5868. doi:10.1016/S0040-4039(00)00636-5.

[14] [14]
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.

[15] [15]
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.

[16] [16]
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.

[17] [17]
Roy, Chandra D.; Brown, Herbert C. 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.

[18] [18]
Raasch, Maynard S. Annulations with tetrachlorothiophene 1,1-dioxide. J. Org. Chem. 1980, 45 (5): 856 – 867. doi:10.1021/jo01293a019.

[19] [19]
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.

[20] [20]
Treutwein, Jonas; Hilt, Gerhard. Cobalt-Catalyzed [2+2] Cycloaddition. Angewandte Chemie, International Edition. 2008, 47 (36): 6811–6813. doi:10.1002/anie.200801778.

[21] [21]
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. （原始内容存档于2023-03-24）.

[22] [22]
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.

[23] [23]
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)

[24] [24]
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.

[25] [25]
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.

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