2-氰基呋喃

2-氰基呋喃
別名	呋喃-2-甲腈; 2-呋喃甲腈; 2-呋喃基氰
識別
CAS號	617-90-3
PubChem	69245
ChemSpider	62458
SMILES	N#Cc1occc1;
InChI	1/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H;
InChIKey	YXDXXGXWFJCXEB-UHFFFAOYAE
性質
化學式	C5H3NO
摩爾質量	93.08 g·mol−1
外觀	無色（不純時呈黃色）
密度	20 °C時為1.0650 g/cm-3
沸點	147 °C（420 K）
危險性
閃點	95 °F（308 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

2-氰基呋喃具有腈基（氰基）的的無色呋喃衍生物。

合成方式

工業上合成2-氰基呋喃主要透過在440-480℃，鉬酸鉍催化劑存在下於氣相環境中，將糠醛與氨混合行氨氧化反應。 ^[3]

實驗室中也有其他合成2-氰基呋喃的方法；例如，使用高價碘試劑^[4]或N-溴代丁二酰亞胺作氧化劑，加入糠醛與氨鹽混合氧化脫水得到2-氰基呋喃、^[5]將糠醛醛肟與亞硫酰氯-苯並三唑、^[6]三苯基膦-碘試劑反應^[7]或在二甲基亞碸（DMSO）中^[8]加熱脫水，以及將糠酰胺透過急驟真空熱解脫水皆可獲取2-氰基呋喃。^[9]

應用

2-氰基呋喃目前沒有大幅度的應用，但它被用作藥物和精細化工合成的中間體。2-氰基呋喃的甜度是蔗糖的30倍左右，因此也被認為是一種可能的甜味劑。^[3]

參考資料

^ P. A. Pavlov; Kul'nevich, V. G. Synthesis of 5-substituted furannitriles and their reaction with hydrazine. Khimiya Geterotsiklicheskikh Soedinenii. 1986, 2: 181–186.
^ 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.
^ ^3.0 ^3.1 Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

[#1-3] 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.

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