2-戊酰呋喃 | 3194-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-戊酰呋喃
• 中文别名: 2-戊酰呋喃,97；2-戊酰基呋喃；2-戊酰呋喃,97%
• 英文名称: 1-furan-2-yl-pentan-1-one
• 英文别名: 2-pentanoylfuran；2-furyl butyl ketone；2-valerylfuran；1-(furan-2-yl)pentan-1-one
• CAS: 3194-17-0
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: HTOZHTBIOGGHDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  108-109 °C
• 密度：
  1.012 g/cm3(Temp: 25 °C)
• LogP：
  2.11
• 物理描述：
  Colourless liquid; Sweet caramel aroma
• 溶解度：
  Slightly soluble in water
• 折光率：
  1.486-1.492
• 保留指数：
  1180

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932190090
• 储存条件：
  室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  2-戊酰呋喃 在 氢氧化钾 、 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 100.0 ℃ 、1.42 MPa 条件下， 反应 3.0h， 生成 1-ethenyl-2-(furan-2-yl)-3-propylpyrrole
  参考文献：
  名称：

  Pyrroles from ketoximes and acetylene

  摘要：

  DOI：

  10.1007/bf00503658
• 作为产物：
  描述：

  2-糠醛缩二乙醇 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 4.03h， 生成 2-戊酰呋喃
  参考文献：
  名称：

  Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones

  摘要：

  Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding alpha-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), alpha-hydroxyalkyl (12 and 13), alpha-aminoalkyl (14) and acyl(15) substituents.

  DOI：

  10.1021/jo00128a039

文献信息

• Direct and Efficient One-Pot Preparation of Ketones from Aldehydes Using <i>N</i>-<i>tert</i>-Butylphenylsulfinimidoyl Chloride
  作者：James J. Crawford、Kenneth W. Henderson、William J. Kerr

  DOI：10.1021/ol061903l

  日期：2006.10.1

  A general, one-pot process has been established to prepare ketones from aldehydes using N-tert-butylphenylsulfinimidoyl chloride. By employing the developed protocol, a range of unsymmetrical ketones has been prepared in good yields from aldehydes in one simple synthetic operation. [reaction: see text]

  已经建立了使用N-叔丁基苯基亚磺酰亚胺基酰氯从醛制备酮的通用的一锅法。通过采用已开发的方案，已通过一种简单的合成操作从醛类以高收率制备了一系列不对称酮。[反应：看文字]
• A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator
  作者：Debasis Sahoo、Sohini Sarkar、Samaresh Jana

  DOI：10.1016/j.tetlet.2019.151084

  日期：2019.9

  An effective process for the conversion of carboxylic acid to ketone has been discovered. In this process, carboxylic acid has been activated using p-toluene sulphonyl group. Under the optimized condition, aromatic, aliphatic heteroaromatic carboxylic acids have been proved to be good substrates for this methodology. The byproduct of this reaction can be removed very easily during work up process.

  已经发现了将羧酸转化为酮的有效方法。在该方法中，使用对甲苯磺酰基将羧酸活化。在最佳条件下，芳香族，脂肪族杂芳族羧酸已被证明是该方法的良好底物。该反应的副产物在后处理过程中可以很容易地除去。同样，一当量的有机金属试剂足以完成该转化。
• Reaction of aldehyde O-alkyl oxime with organometallic compounds
  作者：Shinichi Itsuno、Koji Miyazaki、Koichi Ito

  DOI：10.1016/s0040-4039(00)84709-7

  日期：1986.1

  Aldehyde O-alkyl oximes were converted into ketones with high yields when they were treated with alkyllithium compounds or Grignard reagents followed by hydrolysis. Amines as reductive alkylation products of aldehyde O-alkyl oximes were also obtained by BH3 reduction before hydrolysis.

  当用烷基锂化合物或格利雅试剂进行处理，然后水解时，醛O-烷基肟被高产率地转化为酮。还通过在水解前通过BH 3还原获得作为醛基O-烷基肟的还原烷基化产物的胺。
• Functionalized ketones by iron mediated reaction of grignard reagents with acyl chlorides
  作者：C. Cardellicchio、V. Fiandanese、G. Marchese、L. Ronzini

  DOI：10.1016/s0040-4039(00)96043-x

  日期：1987.1

  The iron(III)-catalyzed cross-coupling reaction between Grignard reagents and acyl chlorides was found to be widely applicable to the synthesis of various functionalized ketones in good yields under mild conditions; the series of examples includes the synthesis of chiral methyl ketones and symmetric diketones.

  发现格氏试剂与酰氯之间的铁（III）催化的交叉偶联反应可广泛用于温和条件下以高收率合成各种功能化的酮。该系列实例包括手性甲基酮和对称二酮的合成。
• Oxidative nucleophilic addition of organovanadium reagents to aldehydes with formation of ketones
  作者：Toshikazu Hirao、Daisuke Misu、Toshio Agawa

  DOI：10.1021/ja00310a073

  日期：1985.11

  En presence de reactifs de Grignard ou de butyl-lithium les benzaldehydes, furfural, alcanals, enaldehydes reagissent avec VCl 3 , conduisant a des cetones

  En存在 de reactifs de Grignard ou de 丁基锂 les benzaldehydes, furfural, alcanals, enaldehydes reagissent avec VCl 3 , conduisant a des cetones