1-(triisopropylsilyl)-1H-indole-3-carbonitrile | 1605284-58-9

• 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: 1-(triisopropylsilyl)-1H-indole-3-carbonitrile
• 英文别名: 1-tri(propan-2-yl)silylindole-3-carbonitrile
• CAS: 1605284-58-9
• 化学式: C₁₈H₂₆N₂Si
• 分子量: 298.503
• InChiKey: VFKBIKNCMKTBBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(triisopropylsilyl)-1H-indole-3-carbonitrile 、 联硼酸频那醇酯 、 频那醇硼烷 在 1,10-菲罗啉 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 正己烷 为溶剂， 反应 24.0h， 生成 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole-3-carbonitrile 、
  参考文献：
  名称：

  Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C–H Borylation

  摘要：

  Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.

  DOI：

  10.1021/jacs.5b07154
• 作为产物：
  描述：

  3-氰基吲哚 、 三异丙基氯硅烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以87%的产率得到1-(triisopropylsilyl)-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C–H Borylation

  摘要：

  Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.

  DOI：

  10.1021/jacs.5b07154

文献信息

• Iron(II)‐Catalyzed Direct Cyanation of Arenes with Aryl(cyano)iodonium Triflates
  作者：Zhibin Shu、Wenzhi Ji、Xi Wang、Yujing Zhou、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201309791

  日期：2014.2.17

  A direct oxidative cyanation of arenes under FeII catalysis with 3,5‐di(trifluoromethyl)phenyl(cyano)iodonium triflate (DFCT) as the cyanating agent has been developed. The reaction is applicable to wide range of aromatic substrates, including polycyclic structures and heteroaromatic compounds.

  已经开发了在Fe II催化下使用3,5-二（三氟甲基）苯基（氰基）碘化三氟甲磺酸盐（DFCT）作为氰化剂的芳烃直接氧化氰化反应。该反应适用于多种芳族底物，包括多环结构和杂芳族化合物。