1-(3-Methyl-2-trimethylsilanyl-indol-1-yl)-ethanone | 135190-01-1

• 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-(3-Methyl-2-trimethylsilanyl-indol-1-yl)-ethanone
• 英文别名: 1-(3-Methyl-2-trimethylsilylindol-1-yl)ethanone
• CAS: 135190-01-1
• 化学式: C₁₄H₁₉NOSi
• 分子量: 245.396
• InChiKey: DFRQXARHRMDMPA-UHFFFAOYSA-N

物化性质

• 熔点：
  65-67 °C
• 沸点：
  327.0±22.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-Methyl-2-trimethylsilanyl-indol-1-yl)-ethanone 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到3-甲基-1-乙酰基-1H-吲哚
  参考文献：
  名称：

  Larock, Richard C.; Yum, Eul Kgun, Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6689 - 6690

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘苯胺 在 palladium diacetate 、 potassium carbonate 、 三乙胺 、 lithium chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 1-(3-Methyl-2-trimethylsilanyl-indol-1-yl)-ethanone
  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

• Larock, Richard C.; Yum, Eul Kgun, Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6689 - 6690
  作者：Larock, Richard C.、Yum, Eul Kgun

  DOI：——

  日期：——
• SYNTHESIS OF 2,3-DISUBSTITUTED INDOLES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALK YNES: 3-METHYL-2-(TRIMETHYLSILYL)INDOLE
  作者：Chen, Yu、Markina, Nataliya A.、Yao, Tuanli、Larock, Richard C.

  DOI：10.15227/orgsyn.088.0377

  日期：——
• 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.