苊

苊
	IUPAC名; 苊
別名	苊烯
識別
CAS號	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
性質
化學式	C12H8
摩爾質量	152.192 g·mol⁻¹
外觀	白色結晶狀粉末
密度	固體
熔點	90-92 ℃
沸點	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
危險性
警示術語	R：R22-R36/37/38
安全術語	S：S26-S36-S37-S39
MSDS	MSDS
閃點	?℃
相關物質
相關化學品	1,2-二氫苊
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

苊^[1]（英語：Acenaphthylene）也常作苊烯，又稱萘並乙烯、1,8-亞乙基萘。是一種含有萘環並通過乙烯橋連萘環1位和8位的多環芳烴類有機化合物。它是煤焦油的成分之一，通過氫化還原分子中的乙烯結構能得到苊。不同於其他大多數多環芳烴化合物，苊烯不發出熒光。

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化學性質及反應

苊分子五元環上的烯烴雙鍵雖然處於環內且與萘環共軛但性質較為活潑，所以涉及苊烯的化學反應主要發生在苊五元環上的烯烴雙鍵上。苊能被一些烷基金屬試劑或鹼金屬比如單質鋰反應，發生去質子化形成苊負離子^[2]，能發生溴代^[3]、鹵素或水的加成反應^[4]^[5]^[6]^[7]^[8]^[9]、環氧化反應、氮雜環丙烷化、氫甲酰化反應^[10]、Heck反應^[11]、碳碳雙鍵的氧化斷裂^[12]、還原^[13]^[14]、硝化^[15]、雙羥基化^[16]^[17]、D-A反應^[18]^[19]、[2+2]環加成^[20]^[21]、1,3-偶極環加成反應^[22]、硼烷對苊的加成^[23]、與芳基酰氯的脫羰基偶聯^[24]等多種反應。

1-溴苊可由苊先經三溴化吡啶鎓的加成，後在鹼存在下發生消除反應製得。^[25]

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另見

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參考文獻

[1]
中國化學會有機化合物命名審定委員會. 有機化合物命名原則 2017. 科學出版社. 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=為空 (幫助)
[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. （原始內容存檔於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=為空 (幫助)
[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.

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[1] [1]
中國化學會有機化合物命名審定委員會. 有機化合物命名原則 2017. 科學出版社. 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=為空 (幫助)

[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. （原始內容存檔於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=為空 (幫助)

[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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