3-phenyl-2-(trimethylsilyl)-1H-indole | 215365-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-phenyl-2-(trimethylsilyl)-1H-indole
• 英文别名: trimethyl-(3-phenyl-1H-indol-2-yl)silane
• CAS: 215365-72-3
• 化学式: C₁₇H₁₉NSi
• 分子量: 265.43
• InChiKey: QWDMVNVWWWXBLU-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  420.5±38.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-(trimethylsilyl)-1H-indole 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以89%的产率得到3-苯基-1H-吲哚
  参考文献：
  名称：

  Synthesis of topologically constrained naphthalimide appended palladium(ii)–N-heterocyclic carbene complexes – insights into additive controlled product selectivity

  摘要：

  Pd（ii）-NHC催化的选择性杂环化合物合成方法已被证明，该方法将o-卤代苯胺和芳基乙炔基三甲基硅烷进行杂环化反应，产生吲哚，并且可以通过添加剂来控制可切换的产物选择性。

  DOI：

  10.1039/c8ob00616d
• 作为产物：
  描述：

  2-碘苯甲酸 、 苯基乙炔基三甲基硅烷 在 palladium diacetate sodium azide 、 氯甲酸苄酯 、 sodium t-butanolate 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以82%的产率得到3-phenyl-2-(trimethylsilyl)-1H-indole
  参考文献：
  名称：

  由2-碘苯甲酸一锅多组分合成吲哚。

  摘要：

  DOI：

  10.1002/anie.200703671

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。
• Palladium-catalyzed annulation of internal alkynes in aqueous medium
  作者：Wei Jie Ang、Chih-Hsuan Tai、Lee-Chiang Lo、Yulin Lam

  DOI：10.1039/c3ra46010j

  日期：——

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.

  为了促进前催化剂的回收和再利用，我们开发了一种氟溶性的、基于肟的钯环化合物1，并证明它是非常高效且多功能的前催化剂，适用于内部炔烃与功能化芳基卤化物在水相介质中的碳环化和杂环化反应。同时，我们还开发了这些环化反应的统一反应条件。
• Synthesis of Fluoren-9-ones by the Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Halobiaryls
  作者：Marino A. Campo、Richard C. Larock

  DOI：10.1021/jo020140m

  日期：2002.8.1

  The synthesis of various substituted fluoren-9-ones has been accomplished by the palladium-catalyzed cyclocarbonylation of o-halobiaryls. The cyclocarbonylation of 4'-substituted 2-iodobiphenyls produces very high yields of 2-substituted fluoren-9-ones bearing either electron-donating or electron-withdrawing substituents. 3'-Substituted 2-iodobiphenyls afford 3-substituted fluoren-9-ones in excellent

  各种取代的芴-9-酮的合成已通过邻卤代联芳基的钯催化环羰基化完成。4′-取代的2-碘联苯的环羰基化产生非常高产率的带有给电子或吸电子取代基的2-取代的芴-9-。3'-取代的2-碘联苯以优异的产率和良好的区域选择性提供3-取代的芴-9-一。该化学方法已成功地扩展到多环芴酮和含有稠合异喹啉，吲哚，吡咯，噻吩，苯并噻吩和苯并呋喃环的芴酮。
• Palladium/NBE-Catalyzed Regioselective C–H Silylation: Access to Divergent Silicon-Containing Indoles
  作者：Wenguang Li、Man Cao、Chunyan Zhang、Shukui Shi、Juan Liu、Wentao Li、Xu Zhang、Yongqi Yu、Ting Li

  DOI：10.1021/acs.orglett.3c04109

  日期：2024.2.16

  A palladium/norbornene (NBE)-catalyzed regioselective C–H silylation of free NH-indoles is reported. This protocol uses Pd(OAc)2 as the catalyst and Cu(OAc)2 as the oxidant, and the reaction relies on the control of NBE as a switch. The reaction tolerates various functional groups, and a series of silicon-containing indoles were directly synthesized in 30%–94% yields.

  报道了钯/降冰片烯 (NBE) 催化的游离 NH-吲哚的区域选择性 C-H 硅烷化反应。该方案以Pd(OAc) 2为催化剂，Cu(OAc) 2为氧化剂，反应依靠NBE作为开关的控制。该反应耐受各种官能团，直接合成了一系列含硅吲哚，收率30%~94%。
• 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.