2-(4-Cyanobutyl)furan | 119216-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(4-Cyanobutyl)furan
• 英文别名: 5-(furan-2-yl)pentanenitrile
• CAS: 119216-39-6
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: GSWHXSFDUHNZJT-UHFFFAOYSA-N

物化性质

• 沸点：
  279.2±23.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  36.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-Cyanobutyl)furan 在 氢氧化钾 、 N,N'-羰基二咪唑 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 N-Methyl-5-(furan-2-yl)pentanamide
  参考文献：
  名称：

  Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems

  摘要：

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.

  DOI：

  10.1021/jo00102a037
• 作为产物：
  描述：

  5-碘戊腈 、 2-(三丁基锡烷基)呋喃 在 (lithium)2(CN)(methyl)2cuprate 作用下， 生成 2-(4-Cyanobutyl)furan
  参考文献：
  名称：

  衍生自2-锂化呋喃的高阶氰基甲酸酯的反应：范围，局限性和合成用途

  摘要：

  描述了对由2-锂化的呋喃与烯酮，环氧化物，醛和卤化物衍生的高级有机铜酸盐的化学性质的一般研究。

  DOI：

  10.1016/0040-4039(88)85081-0

文献信息

• Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles
  作者：Yifeng Chen、Justin P. Romaire、Timothy R. Newhouse

  DOI：10.1021/jacs.5b02243

  日期：2015.5.13

  A highly practical and general palladium-catalyzed methodology for the alpha,beta-dehydrogenation of esters and nitriles is repotted. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of alpha,beta-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible beta-hydride elimination and turnover-limiting, propene-forming reductive elimination.
• Reactions of higher order cyanocuprates derived from 2-lithiated furans: scope, limitations, and synthetic utility
  作者：John S Ng、James R Behling、Arthur L Campbell、Duy Nguyen、Bruce Lipshutz

  DOI：10.1016/0040-4039(88)85081-0

  日期：1988.1

  A general study on the chemistry of higher order organocuprates derived from 2-lithiated furans with enones, epoxides, aldehydes and halides is described.

  描述了对由2-锂化的呋喃与烯酮，环氧化物，醛和卤化物衍生的高级有机铜酸盐的化学性质的一般研究。
• Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems
  作者：Albert Padwa、Donald L. Hertzog、William R. Nadler

  DOI：10.1021/jo00102a037

  日期：1994.11

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.