N-Methyl-<5-(1-methyl-1H-indol-2-yl)pentanoyl>-2-diazo-3-oxobutyramide | 165532-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-Methyl-<5-(1-methyl-1H-indol-2-yl)pentanoyl>-2-diazo-3-oxobutyramide
• 英文别名: N-(2-diazo-3-oxobutanoyl)-N-methyl-5-(1-methylindol-2-yl)pentanamide
• CAS: 165532-93-4
• 化学式: C₁₉H₂₂N₄O₃
• 分子量: 354.409
• InChiKey: YUWVOAJWUIJRGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 N-Methyl-<5-(1-methyl-1H-indol-2-yl)pentanoyl>-2-diazo-3-oxobutyramide 在 rhodium(II) acetate dimer 作用下， 以 苯 为溶剂， 反应 1.5h， 以77%的产率得到1-Acetyl-4,8-diaza-8-methyl-7-<4-(1-methyl-1H-indol-2-yl)butyl>-4-phenyl-10-oxotricyclo<5.2.1.0^2,6>decane-3,5,9-trione
  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：

  1-Benzenesulfonyl-2-(4-bromobutanyl)-1H-indole 在 氢氧化钾 、 sodium hydroxide 、 正丁基锂 、 四丁基硫酸氢铵 、 三乙胺 、 甲烷磺酰基叠氮化物 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二甲基亚砜 、 乙腈 、 苯 为溶剂， 反应 46.0h， 生成 N-Methyl-<5-(1-methyl-1H-indol-2-yl)pentanoyl>-2-diazo-3-oxobutyramide
  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