1-(dimethylphenylsilyl)indole | 1343516-53-9

• 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: 1-(dimethylphenylsilyl)indole
• 英文别名: Indol-1-yl-dimethyl-phenylsilane
• CAS: 1343516-53-9
• 化学式: C₁₆H₁₇NSi
• 分子量: 251.403
• InChiKey: YFIOANVZVYJSFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(dimethylphenylsilyl)indole 、 dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 dimethyl 2-(2-(1-(dimethyl(phenyl)silyl)-1H-indol-3-yl)-2-(4-methoxyphenyl)ethyl)malonate
  参考文献：
  名称：

  Asymmetric Synthesis of Indole Homo-Michael Adducts via Dynamic Kinetic Friedel–Crafts Alkylation with Cyclopropanes

  摘要：

  An enantioconvergent Friedel-Crafts alkylation of indoles with donor-acceptor cyclopropanes is described. The reaction is catalyzed by pybox center dot Mgl(2) and proceeds via a type I dynamic kinetic asymmetric transformation (DyKAT).

  DOI：

  10.1021/ol4010646
• 作为产物：
  描述：

  吲哚 在 dirhodium tetraacetate 、 tetrabutylammonium tungstate 作用下， 以 乙腈 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以99%的产率得到1-(dimethylphenylsilyl)indole
  参考文献：
  名称：

  Hydrosilylation of Various Multiple Bonds by a Simple Combined Catalyst of a Tungstate Monomer and Rhodium Acetate

  摘要：

  在钨酸盐单体（TBA2WO4，TBA：四正丁基铵）和乙酸铑（Rh2(OAc)4）的简单组合催化剂存在下，酮、醛、二氧化碳、烯烃、腈和呋喃衍生物等各种类型的物质高效进行氢硅烷化反应，以中等至高产率（≥63%产率）得到相应的氢硅烷化产物。此外，该体系还可用于苯甲酰胺一步还原为苄胺（产率95%）。

  DOI：

  10.1246/cl.130338

文献信息

• Ru 3 (CO) 12 -catalyzed dehydrogenative Si N coupling of indoles with hydrosilanes without additive
  作者：Wenchao Zhai、Bin Li、Baiquan Wang

  DOI：10.1016/j.tet.2018.01.024

  日期：2018.3

  An efficient Ru3(CO)12-catalyzed dehydrogenative SiN coupling reaction of indoles, pyrrole, and carbazole with hydrosilanes is reported. The reaction does not need any external additive. This catalytic reaction has a wide substrate range, excellent functional group tolerance, and high to excellent reaction efficiency. Gram-scale synthesis demonstrates the practicability of this synthetic method.

  报道了吲哚，吡咯和咔唑与氢化硅烷的有效Ru 3（CO）12催化的脱氢Si N偶联反应。该反应不需要任何外部添加剂。该催化反应具有宽的底物范围，优异的官能团耐受性以及高至优异的反应效率。克级合成证明了这种合成方法的实用性。
• Zinc-Catalyzed Dehydrogenative N-Silylation of Indoles with Hydrosilanes
  作者：Teruhisa Tsuchimoto、Yoshihiko Iketani、Masaru Sekine

  DOI：10.1002/chem.201200651

  日期：2012.7.27

  Zinc catalysis: Zinc triflate in a nitrile solvent behaved as an effective catalyst for dehydrogenative N‐silylation with a variety of indoles and hydrosilanes (see scheme). The addition of pyridine greatly accelerated the N‐silylation reaction to produce N‐silylindoles exclusively in high to excellent yields.

  锌催化：在腈溶剂中的三氟甲磺酸锌可作为有效的催化剂，用于与各种吲哚和氢硅烷进行脱氢N-硅烷化反应（请参见方案）。吡啶的加入极大地加速了N-甲硅烷基化反应，从而以高产率至优异产率生产N-甲硅烷基。
• Rhodium acetate/base-catalyzed N-silylation of indole derivatives with hydrosilanes
  作者：Shintaro Itagaki、Keigo Kamata、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1039/c2cc34381a

  日期：——

  In the presence of Rh(2)(OAc)(4) (OAc = acetate) and TBA(2)WO(4) (TBA = tetra-n-butylammonium), the N-silylation of indole derivatives with hydrosilanes efficiently proceeded to give the corresponding N-silylated indoles in high yields. Pyrrole and carbazole were also N-silylated with the combined catalysts.

  在铑（2）（OAc）（4）（OAC =乙酸盐）和TBA的存在下（2）WO（4）（TBA =四正丁基铵），吲哚衍生物与氢硅烷的N甲硅烷基化有效地进行到以高收率得到相应的N-甲硅烷基化的吲哚。吡咯并咔唑，也可为N-甲硅烷基化与所述组合的催化剂。
• Catalytic dehydrogenative Si–N coupling of pyrroles, indoles, carbazoles as well as anilines with hydrosilanes without added base
  作者：C. David F. Königs、Maria F. Müller、Nuria Aiguabella、Hendrik F. T. Klare、Martin Oestreich

  DOI：10.1039/c3cc38900f

  日期：——

  A base-free, catalytic protocol for the dehydrogenative Si-N coupling of weakly nucleophilic N-H groups of heteroarenes or aryl-substituted amines with equimolar amounts of hydrosilanes is reported. Cooperative Si-H bond activation at a Ru-S bond generates a silicon electrophile that forms a Si-N bond prior to the N-H deprotonation by an intermediate Ru-H complex, only releasing H(2).

  报道了用于等芳烃或等摩尔量的氢化芳烃的杂芳烃或芳基取代的胺的弱亲核NH基团的脱氢Si-N偶联的无碱催化方案。在Ru-S键上协同激活Si-H键会生成亲电子体，该亲电体在中间Ru-H配合物使NH脱质子化之前形成Si-N键，仅释放H（2）。
• Asymmetric Synthesis of Indole Homo-Michael Adducts via Dynamic Kinetic Friedel–Crafts Alkylation with Cyclopropanes
  作者：Steven M. Wales、Morgan M. Walker、Jeffrey S. Johnson

  DOI：10.1021/ol4010646

  日期：2013.5.17

  An enantioconvergent Friedel-Crafts alkylation of indoles with donor-acceptor cyclopropanes is described. The reaction is catalyzed by pybox center dot Mgl(2) and proceeds via a type I dynamic kinetic asymmetric transformation (DyKAT).