4-methoxy-1-methyl-1H-indole-3-carbonitrile | 889942-81-8

• 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: 4-methoxy-1-methyl-1H-indole-3-carbonitrile
• 英文别名: 4-methoxy-1-methylindole-3-carbonitrile
• CAS: 889942-81-8
• 化学式: C₁₁H₁₀N₂O
• mdl: MFCD07776622
• 分子量: 186.213
• InChiKey: CFKYRYZTUZJZPR-UHFFFAOYSA-N

物化性质

• 沸点：
  366.2±22.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 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：

  2-((((4-methoxy-1-methyl-1H-indol-3-yl)methylene)amino)oxy)-2-methylpropanoic acid 在 四丁基醋酸铵 作用下， 以 甲醇 、 乙腈 为溶剂， 以92%的产率得到4-methoxy-1-methyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  通过氧化脱羧/N-O裂解从α-亚氨基-含氧酸电合成（杂）芳基腈

  摘要：

  通过 α-亚氨基-含氧酸的电化学氧化脱羧，开发了一种通过亚氨基自由基合成（杂）芳基腈的新方法。该协议为在环境条件下具有广泛的官能团耐受性的腈提供了一种有效的方法，可用于一锅克级合成。

  DOI：

  10.1039/d2cc02986c

文献信息

• The palladium-catalyzed cyanation of indole C–H bonds with the combination of NH4HCO3 and DMSO as a safe cyanide source
  作者：Xinyi Ren、Jianbin Chen、Fan Chen、Jiang Cheng

  DOI：10.1039/c1cc11603g

  日期：——

  A palladium-catalyzed cyanation of the 3-position of indole sp2 C–H bonds by the combination of NH4HCO3 and DMSO as the “CN” source was achieved to provide aromatic nitriles in moderate to good yields with excellent regioselectivity. It represents a practical and safe cyanation method.

  实现了通过NH4HCO3和DMSO组合作为“CN”源，钯催化的吲哚3-位sp2 C–H键的氰化反应，以中等至良好的产率得到了具有优异区域选择性的芳香腈。这代表了一种实用且安全的氰化方法。
• Palladium-Catalyzed Directed Carbon–Carbon Bond Activation of Aryl Nitriles for Cyano Transfer
  作者：Lin Tan、Yang Pan、Qing-Ying Zeng、Zhen-Yu Wang、Hui Xu、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.4c00429

  日期：2024.3.22

  Herein, we report the C–H cyanation of indoles via a palladium-catalyzed directed C–CN activation reaction using aryl nitrile as a cyano source. The employment of the phenoxy-oriented group is the key to the cleavage of the C–CN bond. This protocol features a broad substrate scope, good efficiency, and high regioselectivity. Furthermore, the practical application of this protocol was showcased in the

  在此，我们报道了使用芳基腈作为氰基源，通过钯催化的定向 C-CN 活化反应进行吲哚的 C-H 氰化。苯氧基取向基团的使用是C-CN键断裂的关键。该方案具有底物范围广、效率高、区域选择性高的特点。此外，该方案的实际应用在吲哚衍生物的后期功能化和合成中得到了展示，吲哚衍生物是通过氰化过程衍生自药物和天然产物。
• An insight on the influence of surface Lewis acid sites for regioselective C H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst
  作者：Venu Boosa、Vishali Bilakanti、Vijay Kumar Velisoju、Naresh Gutta、Sreedhar Inkollu、Venugopal Akula

  DOI：10.1016/j.mcat.2017.11.007

  日期：2018.2

  The dispersed on mesoporous SBA-15 has demonstrated the regioselective C-H bond C-3-cyanation of indoles by in-situ generation of -CN using DMF and NH4I in presence of O-2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano-group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle. (C) 2017 Elsevier B.V. All rights reserved.