5-methoxy-1,2-dimethyl-1H-indole-3-carbonitrile | 296264-05-6

• 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: 5-methoxy-1,2-dimethyl-1H-indole-3-carbonitrile
• 英文别名: 1H-indole-3-carbonitrile, 5-methoxy-1,2-dimethyl-；5-methoxy-1,2-dimethylindole-3-carbonitrile
• CAS: 296264-05-6
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: BKMKLRANIJNLPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4'-甲氧基乙酰苯胺 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 三氟化硼乙醚 、 copper diacetate 、 sodium hydride 、 silver carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 5-methoxy-1,2-dimethyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Synthesis of indoles through Rh(III)-catalyzed C–H cross-coupling with allyl carbonates

  摘要：

  A practical Rh-catalyzed reaction was developed to achieve 2-alkyl-substituted indole synthesis. The reaction can tolerate a variety of synthetically important functional groups. The indole products can also be transformed into other important skeletons. Two bioactive compounds, that is indomethacin and pravadoline were prepared using the new method. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.11.065

文献信息

• Palladium-Catalyzed Direct Cyanation of Indoles with K₄[Fe(CN)₆]
  作者：Guobing Yan、Chunxiang Kuang、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol1000439

  日期：2010.3.5

  Direct cyanation of indole derivatives has been achieved with nontoxic K4[Fe(CN)6] as cyanating agent through Pd-catalyzed C−H bond activation.

  通过无毒的K 4 [Fe（CN）6 ]作为氰化剂，通过Pd催化的CH键活化，可以实现吲哚衍生物的直接氰化。
• Lewis Acid Catalyzed Direct Cyanation of Indoles and Pyrroles with <i>N</i>-Cyano-<i>N</i>-phenyl-<i>p</i>-toluenesulfonamide (NCTS)
  作者：Yang Yang、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol202335p

  日期：2011.10.21

  BF3·OEt2-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.

  BF 3 ·OEt 2使用毒性较小，稳定且易于处理的亲电子氰化剂，将吲哚和吡咯直接氰化N-氰基-N-苯基-对甲苯磺酰胺（NCTS）可提供3-氰基吲哚和2-氰基吡咯产量高，区域选择性好。关于吲哚和吡咯，底物范围很广。
• Synthesis of indoles through Rh(III)-catalyzed C–H cross-coupling with allyl carbonates
  作者：Tian-Jun Gong、Wan-Min Cheng、Wei Su、Bin Xiao、Yao Fu

  DOI：10.1016/j.tetlet.2013.11.065

  日期：2014.3

  A practical Rh-catalyzed reaction was developed to achieve 2-alkyl-substituted indole synthesis. The reaction can tolerate a variety of synthetically important functional groups. The indole products can also be transformed into other important skeletons. Two bioactive compounds, that is indomethacin and pravadoline were prepared using the new method. (C) 2014 Published by Elsevier Ltd.