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苊

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提示：此條目頁的主題不是1,2-二氫苊。
苊
IUPAC名
苊
別名 苊烯
識別
CAS號 208-96-8  checkY
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
莫耳質量 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，苊烯不發出螢光。

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、氫甲醯化反應[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]、與芳基醯氯的脫羰基偶聯[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]

另見

參考文獻

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  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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