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2-氰基呋喃

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2-氰基呋喃
别名 呋喃-2-甲腈; 2-呋喃甲腈; 2-呋喃基氰
识别
CAS号 617-90-3  checkY
PubChem 69245
ChemSpider 62458
SMILES
 
  • N#Cc1occc1
InChI
 
  • 1/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H
InChIKey YXDXXGXWFJCXEB-UHFFFAOYAE
性质
化学式 C5H3NO
摩尔质量 93.08 g·mol−1
外观 无色(不纯时呈黄色)
密度 20 °C时为1.0650 g/cm-3[1]
沸点 147 °C(420 K)[2]
危险性
闪点 95 °F(308 K)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

2-氰基呋喃具有基(氰基)的的无色呋喃衍生物。

合成方式

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工业上合成2-氰基呋喃主要透过在440-480℃,钼酸铋催化剂存在下于气相环境中,将糠醛混合行氨氧化反应[3]

实验室中也有其他合成2-氰基呋喃的方法;例如,使用高价碘试剂[4]N-溴代丁二酰亚胺作氧化剂,加入糠醛与盐混合氧化脱水得到2-氰基呋喃、[5]将糠醛醛肟亚硫酰氯-苯并三唑[6]三苯基膦-试剂反应[7]或在二甲基亚砜(DMSO)中[8]加热脱水,以及将糠酰胺透过急骤真空热解脱水皆可获取2-氰基呋喃。[9]

应用

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2-氰基呋喃目前没有大幅度的应用,但它被用作药物和精细化工合成的中间体。2-氰基呋喃的甜度是蔗糖的30倍左右,因此也被认为是一种可能的甜味剂。[3]

参考资料

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  1. ^ P. A. Pavlov; Kul'nevich, V. G. Synthesis of 5-substituted furannitriles and their reaction with hydrazine. Khimiya Geterotsiklicheskikh Soedinenii. 1986, 2: 181–186. 
  2. ^ Patrice Capdevielle; Lavigne, Andre; Maumy, Michel. Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles. Synthesis. 1989, 6: 451–452. doi:10.1055/s-1989-27285. 
  3. ^ 3.0 3.1 Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)
  4. ^ Chenjie Zhu; Sun, Chengguo; Wei, Yunyang. Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent. Synthesis. 2010, 24: 4235–4241. doi:10.1055/s-0030-1258281. 
  5. ^ Bandgar, B. P.; Makone, S. S. Organic Reactions in Water: Transformation of Aldehydes to Nitriles using NBS under Mild Conditions. Synthetic Communications. 2006, 36 (10): 1347–1352. ISSN 0039-7911. doi:10.1080/00397910500522009. 
  6. ^ Sachin S. Chaudhari; Akamanchi, Krishnacharya G. Thionyl chloride-benzotriazole: an efficient system for transformation of aldoximes to nitriles. Synthetic Communications. 1999, 29 (10): 1741–1745. doi:10.1080/00397919908086161. 
  7. ^ A. Narsaiah; Sreenu, D.; Nagaiah, K. Triphenylphosphine-iodine. An efficient reagent system for the synthesis of nitriles from aldoximes. Synthetic Communications. 2006, 36 (2): 137–140. doi:10.1080/00397910500333225. 
  8. ^ Aspinall, Helen C.; Beckingham, Oliver; Farrar, Michael D.; Greeves, Nicholas; Thomas, Christopher D. A general and convenient route to oxazolyl ligands. Tetrahedron Letters. 2011, 52 (40): 5120–5123. ISSN 0040-4039. doi:10.1016/j.tetlet.2011.07.070. 
  9. ^ Jacqueline A. Campbell; McDougald, Graham; McNab, Hamish. Laboratory-scale synthesis of nitriles by catalyzed dehydration of amides and oximes under flash vacuum pyrolysis (FVP) conditions. Synthesis. 2007, 20: 3179–3184. doi:10.1055/s-2007-990782.