5-(噻吩-2-基)戊腈 | 26359-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 5-(噻吩-2-基)戊腈
• 英文名称: 2-(4-Cyanobutyl)thiophene
• 英文别名: 5-(thiophen-2-yl)pentanenitrile；5-(Thiophen-2-yl)pentanenitrile；5-thiophen-2-ylpentanenitrile
• CAS: 26359-28-4
• 化学式: C₉H₁₁NS
• 分子量: 165.259
• InChiKey: BZSMFZOCOMELQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(噻吩-2-基)戊腈 在 rhodium(II) acetate dimer 氢氧化钾 、 三乙胺 、 甲烷磺酰基叠氮化物 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 乙腈 、 xylene 、 苯 为溶剂， 反应 4.0h， 生成 7-Acetyl-4,7-epoxy-2,3,3a,4,5,6,7,7a-octahydro-5-methyl-2-phenyl-1,3,6-trioxo-4-<4-(thiophene-2-yl)butyl>-1H-pyrrolo<3,4-c>pyridine
  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：

  3-(2-噻吩基)-1-丙醇 、 乙腈 在 caesium carbonate 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 作用下， 反应 12.33h， 以52%的产率得到5-(噻吩-2-基)戊腈
  参考文献：
  名称：

  铱配合物催化伯醇对乙腈单烷基化

  摘要：

  在铱催化剂的存在下，乙醇被伯醇单烷基化的反应是按一锅法完成的。从芳基和烷基甲醇中获得了各种腈，收率很高。

  DOI：

  10.1021/ol2015972

文献信息

• Monoalkylation of Acetonitrile by Primary Alcohols Catalyzed by Iridium Complexes
  作者：Bruno Anxionnat、Domingo Gomez Pardo、Gino Ricci、Janine Cossy

  DOI：10.1021/ol2015972

  日期：2011.8.5

  The monoalkylation of acetonitrile by primary alcohols was achieved in a one-pot sequence in the presence of iridium catalysts. A diversity of nitriles has been obtained from aryl- and alkyl-methanols in excellent yield.

  在铱催化剂的存在下，乙醇被伯醇单烷基化的反应是按一锅法完成的。从芳基和烷基甲醇中获得了各种腈，收率很高。
• 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.