2-(1-Methyl-1H-indol-3-yl)-3-oxo-butyronitrile | 922184-73-4

• 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: 2-(1-Methyl-1H-indol-3-yl)-3-oxo-butyronitrile
• 英文别名: 2-(1-Methylindol-3-yl)-3-oxobutanenitrile；2-(1-methylindol-3-yl)-3-oxobutanenitrile
• CAS: 922184-73-4
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: ATXCRCPDUGDUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-Methyl-1H-indol-3-yl)-3-oxo-butyronitrile 、 甲氧基胺盐酸盐 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以85%的产率得到3-methoxyimino-2-(1-methyl-1H-indol-3-yl)butyronitrile
  参考文献：
  名称：

  Formation of N-Alkoxyindole Framework:  Intramolecular Heterocyclization of 3-Alkoxyimino-2-arylalkylnitriles Mediated by Ferric Chloride

  摘要：

  [GRAPHICS]A variety of functionalized N-alkoxyindole-3-carbonitrile derivatives are achieved under remarkably mild conditions by applying a FeCl3-mediated intramolecular heterocyclization of 3-alkoxyimino-2-arylalkylnitliles. This novel synthesis allows the N-moiety on the side chain to be annulated to the benzene ring as the final synthetic step, which enables the functionalization of the benzenoid portion of the indole at an early stage of the synthesis.

  DOI：

  10.1021/jo7024477
• 作为产物：
  描述：

  1-甲基吲哚-3-乙腈 、 乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(1-Methyl-1H-indol-3-yl)-3-oxo-butyronitrile
  参考文献：
  名称：

  Synthesis of N-Substituted Indole Derivatives via PIFA-Mediated Intramolecular Cyclization

  摘要：

  A variety of N- arylated and N- alkylated indole derivatives were synthesized by way of a phenyliodine bis( trifluoroacetate) ( PIFA)- mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N- atom on the side chain to the benzene ring at the last synthetic step. Other novel pyrrole- fused aromatic compounds can also be achieved by this method.

  DOI：

  10.1021/ol062288o

文献信息

• Synthesis of N-Substituted Indole Derivatives via PIFA-Mediated Intramolecular Cyclization
  作者：Yunfei Du、Renhe Liu、Gregory Linn、Kang Zhao

  DOI：10.1021/ol062288o

  日期：2006.12.1

  A variety of N- arylated and N- alkylated indole derivatives were synthesized by way of a phenyliodine bis( trifluoroacetate) ( PIFA)- mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N- atom on the side chain to the benzene ring at the last synthetic step. Other novel pyrrole- fused aromatic compounds can also be achieved by this method.
• Formation of <i>N</i>-Alkoxyindole Framework:  Intramolecular Heterocyclization of 3-Alkoxyimino-2-arylalkylnitriles Mediated by Ferric Chloride
  作者：Yunfei Du、Junbiao Chang、John Reiner、Kang Zhao

  DOI：10.1021/jo7024477

  日期：2008.3.1

  [GRAPHICS]A variety of functionalized N-alkoxyindole-3-carbonitrile derivatives are achieved under remarkably mild conditions by applying a FeCl3-mediated intramolecular heterocyclization of 3-alkoxyimino-2-arylalkylnitliles. This novel synthesis allows the N-moiety on the side chain to be annulated to the benzene ring as the final synthetic step, which enables the functionalization of the benzenoid portion of the indole at an early stage of the synthesis.