6-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole | 1363623-61-3

• 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: 6-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
• 英文别名: 6-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS: 1363623-61-3
• 化学式: C₁₅H₂₀BNO₃
• 分子量: 273.14
• InChiKey: LXZCPPRNPHICPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 以96%的产率得到6-methoxy-7-hydroxyindole
  参考文献：
  名称：

  Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones

  摘要：

  An iridium-catalyzed C-H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C-H functionalization strategy delivers 7-borylindoles that undergo facile oxidation hydrolysis to 7-hydroyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.

  DOI：

  10.1021/jo300330u
• 作为产物：
  描述：

  6-甲氧基吲哚 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium acetate 、 联硼酸频那醇酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 32.0h， 生成 6-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
  参考文献：
  名称：

  Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones

  摘要：

  An iridium-catalyzed C-H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C-H functionalization strategy delivers 7-borylindoles that undergo facile oxidation hydrolysis to 7-hydroyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.

  DOI：

  10.1021/jo300330u

文献信息

• Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones
  作者：Christy Wang、Jonathan Sperry

  DOI：10.1021/jo300330u

  日期：2012.3.16

  An iridium-catalyzed C-H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C-H functionalization strategy delivers 7-borylindoles that undergo facile oxidation hydrolysis to 7-hydroyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.