2-[2-(2-hydroxypropan-2-yl)-1H-indol-3-yl]propan-2-ol | 215365-69-8

• 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: 2-[2-(2-hydroxypropan-2-yl)-1H-indol-3-yl]propan-2-ol
• CAS: 215365-69-8
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: BFNLBRYYYFADNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  56.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-碘苯胺 、 2,5-二甲基-3-己炔-2,5-二醇 在 palladium diacetate 、 四丁基氯化铵 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以54%的产率得到2-[2-(2-hydroxypropan-2-yl)-1H-indol-3-yl]propan-2-ol
  参考文献：
  名称：

  Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes

  摘要：

  The palladium-catalyzed coupling of 2-iodoaniline and the corresponding N-methyl, -acetyl, and -tosyl derivatives with a wide variety of internal alkynes provides 2,3-disubstituted indoles in good-to-excellent yields. The best results are obtained by employing an excess of the alkyne and a sodium or potassium acetate or carbonate base plus 1 equiv of either LiCl or n-Bu4NCl, occasionally adding 5 mol % PPh3. The yields with LiCl appear to be higher and more reproducible than those obtained with n-Bu4NCl. The process is quite general as far as the types of substituents which can be accommodated on the nitrogen of the aniline and the two ends of the alkyne triple bond. The reaction is quite regioselective, placing the aryl group of the aniline on the less sterically hindered end of the triple bond and the nitrogen moiety on the more sterically hindered end. This methodology readily affords 2-silylindoles, which can be easily protodesilylated, halogenated, or reacted with alkenes and Pd(OAc)(2) to produce 3-substituted indoles, 2-haloindoles, or 2-(1-alkenyl)indoles, respectively. The presence of alcohol groups in the alkyne seems to have a particularly strong directing effect, perhaps due to coordination with palladium. This catalytic process apparently involves arylpalladium formation, regioselective addition to the C-C triple bond of the alkyne, and subsequent intramolecular palladium displacement.

  DOI：

  10.1021/jo9803277

文献信息

• Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes
  作者：R. C. Larock、E. K. Yum、M. D. Refvik

  DOI：10.1021/jo9803277

  日期：1998.10.1

  The palladium-catalyzed coupling of 2-iodoaniline and the corresponding N-methyl, -acetyl, and -tosyl derivatives with a wide variety of internal alkynes provides 2,3-disubstituted indoles in good-to-excellent yields. The best results are obtained by employing an excess of the alkyne and a sodium or potassium acetate or carbonate base plus 1 equiv of either LiCl or n-Bu4NCl, occasionally adding 5 mol % PPh3. The yields with LiCl appear to be higher and more reproducible than those obtained with n-Bu4NCl. The process is quite general as far as the types of substituents which can be accommodated on the nitrogen of the aniline and the two ends of the alkyne triple bond. The reaction is quite regioselective, placing the aryl group of the aniline on the less sterically hindered end of the triple bond and the nitrogen moiety on the more sterically hindered end. This methodology readily affords 2-silylindoles, which can be easily protodesilylated, halogenated, or reacted with alkenes and Pd(OAc)(2) to produce 3-substituted indoles, 2-haloindoles, or 2-(1-alkenyl)indoles, respectively. The presence of alcohol groups in the alkyne seems to have a particularly strong directing effect, perhaps due to coordination with palladium. This catalytic process apparently involves arylpalladium formation, regioselective addition to the C-C triple bond of the alkyne, and subsequent intramolecular palladium displacement.