呋喃

呋喃
Full displayed formula of furan
Skeletal formula showing numbering convention
IUPAC名
Furan
系统名
1-Oxacyclopenta-2,4-diene
1-氧杂-2,4-环戊二烯
别名 氧杂茂
𫫇茂
1,4-環氧-1,3-丁二烯
识别
CAS号 110-00-9  checkY
PubChem 8029
ChemSpider 7738
SMILES
 
  • c1ccoc1
InChI
 
  • 1/C4H4O/c1-2-4-5-3-1/h1-4H
InChIKey YLQBMQCUIZJEEH-UHFFFAOYAC
KEGG C14275
性质
化学式 C₄H₄O
摩尔质量 68.07 g·mol⁻¹
外观 无色易挥发液体
密度 0.936 g/mL
熔点 -85.6 °C
沸点 31.4 °C
危险性
闪点 -35 °C
相关物质
相关杂环 吡咯
噻吩
相关化学品 四氢呋喃(THF)
2,5-二甲基呋喃
苯并呋喃
二苯并呋喃
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

呋喃(英語:furan),化学用名氧杂茂[1]𫫇茂(英語:Oxole),是杂环有机物,其五元芳环有四粒原子和一粒原子。有呋喃环的化合物為其同系物。呋喃是无色、可燃、易挥发液体,沸点接近室温。呋喃有且為2B類可能致物質。[2]常作为合成其他复杂有机物的起始原料。[3]性质与相似,可由松木蒸馏得到,可溶於丙酮、醇、醚等多種常見有機溶劑,微溶於水。為多种重要工業化學品與藥物的前驅體,如常用作溶劑的四氢呋喃[4]

历史

“呋喃”的英文单词furan来自拉丁文单词furfur米糠)。[5]1780年,卡尔·威廉·舍勒发现2-糠酸,是最先发现的呋喃衍生物;1831年,德贝莱纳报道另一种重要衍生物糠醛;1870年,有德国化学家成功制备呋喃。[6][7]

製取

工业可由催化糠醛羰基生产呋喃,或用氯化铜水溶液催化氧化1,3-丁二烯[3]

实验室中,可先将糠醛氧化为呋喃-2-甲酸,再脱羧成呋喃[8]。也可热分解戊糖获得;也可用固体纤维素,尤其松木

Feist-Bénary合成是经典合成路线。帕尔-克诺尔合成用1,4-二酮与五氧化二磷反应,是简单的方法。另外,回收噻吩的合成工艺中, 1,4-二酮和劳森试剂反应的副产品也可以得到呋喃。

化学性质

呋喃的氧原子有对孤对电子共轭轨道平面形成大Π键,共轭平面共6粒电子,符合4n+2規則,是芳香物(见休克尔规则),“易取代难加成”。氧的另外一对孤对电子向外伸展。氧原子本身符合sp2杂化

芳环使呋喃的化学行为不太似其它不饱和杂环。

Resonance contributors of furan

Furan Diels-Alder reaction with ethyl (E)-3-nitroacrylate

鉴定

盐酸浸过的松木片和呋喃作用,松木片会显绿色。[11]

参考文献

  1. ^ 循菌,氧(雜)茂--樂詞網. terms.naer.edu.tw. [2023-05-11]. (原始内容存档于2023-05-11). 
  2. ^ Bakhiya, Nadiya; Appel, Klaus E. Toxicity and carcinogenicity of furan in human diet. Archives of Toxicology. 2010-07-01, 84 (7): 563–578 [2018-04-12]. ISSN 0340-5761. doi:10.1007/s00204-010-0531-y. (原始内容存档于2020-04-10) (英语). 
  3. ^ 3.0 3.1 H. E. Hoydonckx, W. M. Van Rhijn, W. Van Rhijn, D. E. De Vos, P. A. Jacobs, Furfural and Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a12_119.pub2 
  4. ^ Junichi Kanetaka, Taisuke Asano, and Shinobu Masamune. New Process for Production of Tetrahydrofuran. Industrial & Engineering Chemistry. 1970, 4 (62): 24-32 [2018-04-12]. doi:10.1021/ie50724a005. (原始内容存档于2020-04-10). 
  5. ^ Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006. ISBN 978-0-444-52239-9.
  6. ^ Limpricht, H. Ueber das Tetraphenol C4H4O. Berichte der deutschen chemischen Gesellschaft. 1870, 3 (1): pp. 90–91. doi:10.1002/cber.18700030129. 
  7. ^ Rodd, Ernest Harry. Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Elsevier. 1971. 
  8. ^ Wilson, W.C. (1941). "Furan". Org. Synth.; Coll. Vol. 1: 274. 
  9. ^ Bruice, Paula Y. Organic Chemistry Fifth. Upper Saddle River, NJ: Pearson Prentice Hall. 2007. ISBN 0-13-196316-3. 
  10. ^ Masesane I, Batsanov A, Howard J, Modal R, Steel P. The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid. Beilstein Journal of Organic Chemistry. 2006, 2 (9): 9. PMC 1524792可免费查阅. PMID 16674802. doi:10.1186/1860-5397-2-9. 
  11. ^ 谷亨杰 等. 有机化学(第二版). 高等教育出版社, 2000.7. pp 381. 吡咯、呋喃和噻吩的鉴定

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