1-methoxy-2-methyl-1H-benzo[g]indole-3-carbonitrile | 1013062-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methoxy-2-methyl-1H-benzo[g]indole-3-carbonitrile
• 英文别名: 1-Methoxy-2-methylbenzo[g]indole-3-carbonitrile
• CAS: 1013062-69-5
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: LYSIZBKVXJKQHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methoxyimino-2-(naphthalen-2-yl)butyronitrile 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以75%的产率得到1-methoxy-2-methyl-1H-benzo[g]indole-3-carbonitrile
  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

文献信息

• Highly Stereoselective Dimerization of 3-Alkoxyimino-2-aryl-alkylnitriles via Oxidative Carbon-Carbon Bond Formation
  作者：Yunfei Du、Kang Zhao、Yongliang Zhang、Songqing Wang

  DOI：10.1055/s-0029-1217369

  日期：2009.7

  The MnO 2 -mediated oxidative dimerization of a series of 3-alkoxyimino-2-aryl-alkylnitriles was investigated. The developed method stereospecifically afforded solely the corresponding C 2 -symmetric dl-dimers, with the trans-configuration of the C=N double bonds, in good to excellent yields under mild conditions. The alkoxyimino substituents in the substrates and a thermodynamically controlled mechanism

  研究了一系列 3-烷氧基亚氨基-2-芳基-烷基腈的 MnO 2 介导的氧化二聚反应。所开发的方法立体定向地仅提供相应的 C 2 -对称 dl-二聚体，具有 C=N 双键的反式构型，在温和条件下以良好到极好的产率。底物中的烷氧基亚氨基取代基和热力学控制的机制被认为对于这种自由基二聚过程的立体选择性是必不可少的。
• 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.