3-methyl-2-(trimethylsilyl)indole | 135189-98-9

• 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: 3-methyl-2-(trimethylsilyl)indole
• 英文别名: 2-trimethylsilyl-3-methyl-1H-indole；3-Methyl-2-(trimethylsilyl)-1H-indole；trimethyl-(3-methyl-1H-indol-2-yl)silane
• CAS: 135189-98-9
• 化学式: C₁₂H₁₇NSi
• 分子量: 203.359
• InChiKey: XSIGGPGSGOQXMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-(三甲基硅基)丙炔 、 2-碘苯胺 在 四丁基氯化铵 、 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 以91%的产率得到3-methyl-2-(trimethylsilyl)indole
  参考文献：
  名称：

  SYNTHESIS OF 2,3-DISUBSTITUTED INDOLES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALK YNES: 3-METHYL-2-(TRIMETHYLSILYL)INDOLE

  摘要：

  DOI：

  10.15227/orgsyn.088.0377

文献信息

• Nickel-catalyzed Heteroannulation of<i>o</i>-Haloanilines with Alkynes
  作者：Yuji Yoshida、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.2011.1067

  日期：2011.10.5

  A nickel-catalyzed heteroannulation has been developed where o-haloanilines react with alkynes to afford 2,3-disubstituted indoles. IPr (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) was found to be an effective ligand for the reaction.

  已开发一种镍催化的杂环合成反应，其中邻卤代苯胺与炔烃反应生成2,3-二取代吲哚。发现IPr（1,3-双(2,6-二异丙基苯基)咪唑-2-亚氮基）是该反应的有效配体。
• 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.
• 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：——