7-ethyl-1-methyl-1H-indole

• 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: 7-ethyl-1-methyl-1H-indole
• 英文别名: 7-Ethyl-N-methylindole；7-ethyl-1-methylindole
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: PNBISRBPZVZDNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  7-ethyl-1-methyl-1H-indole 在 邻硝基苯甲酸 、 [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]tris(4-fluorophenyl)phosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 、 palladium diacetate 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 138.0h， 生成 6-ethyl-5,10-dimethyl-10-phenyl-5,10-dihydrobenzo[4,5]silolo[3,2-b]indole
  参考文献：
  名称：

  Catalytic Access to Indole-Fused Benzosiloles by 2-Fold Electrophilic C–H Silylation with Dihydrosilanes

  摘要：

  A protocol for the catalytic synthesis of indole-fused benzosiloles starting from 2-aryl-substituted indoles and dihydrosilanes is reported. Compared to known procedures, this method does not require prefunctionalized, starting materials and, hence, allows for a rapid access to those siloles. The net reaction is a 2-fold electrophilic C-H silylation catalyzed by cationic Ru-S complexes. Both reaction steps were separately investigated, and these results eventually led to the development of a two-step procedure. By preparing new Ru-S complexes with different weakly coordinating anions (WCAs), it is also shown that the latter can have a dramatic influence on the outcome of these reactions. Furthermore, the substrate scope of the new method is discussed.

  DOI：

  10.1021/acs.organomet.6b00801
• 作为产物：
  描述：

  7-乙基吲哚 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 7-ethyl-1-methyl-1H-indole
  参考文献：
  名称：

  通过协同 B-H 键活化催化生成硼离子：氮杂环与频哪硼烷的难以捉摸的直接亲电硼酸化

  摘要：

  典型硼烷的 BH 键被束缚的钌 (II) 硫醇盐络合物的极性 Ru-S 键异裂，提供氢化钌 (II) 和硼离子，并与硫原子发生配价相互作用。这些稳定的加合物经过光谱表征，在一种情况下，BH 键激活步骤在晶体学上得到验证，这是 σ 键复分解的快照。源自 9-硼双环 [3.3.1] 壬烷二聚体 [(9-BBN)2]、频哪醇硼烷 (pinBH) 和儿茶酚硼烷 (catBH) 的硼离子允许吲哚的亲电芳香取代。针对各种氮杂环进一步阐述了前所未有的 pinB 阳离子亲电硼酸化。

  DOI：

  10.1021/ja405925w

文献信息

• Rh(III)-Catalyzed C–C/C–N Coupling of Imidates with α-Diazo Imidamide: Synthesis of Isoquinoline-Fused Indoles
  作者：He Wang、Lei Li、Songjie Yu、Yunyun Li、Xingwei Li

  DOI：10.1021/acs.orglett.6b01284

  日期：2016.6.17

  Imidate esters and diazo compounds have been established as bifunctional substrates for the construction of biologically active fused heterocycles via rhodium-catalyzed C–H activation and C–C/C–N coupling. This reaction occurs under mild conditions with high efficiency, step economy, and low catalyst loading.

  酰亚胺酯和重氮化合物已被确定为通过铑催化的C–H活化和C–C / C–N偶联构建具有生物活性的稠合杂环的双功能底物。该反应在温和的条件下以高效率，分步经济性和低催化剂负载进行。
• Catalytic Generation of Borenium Ions by Cooperative B–H Bond Activation: The Elusive Direct Electrophilic Borylation of Nitrogen Heterocycles with Pinacolborane
  作者：Timo Stahl、Kristine Müther、Yasuhiro Ohki、Kazuyuki Tatsumi、Martin Oestreich

  DOI：10.1021/ja405925w

  日期：2013.7.31

  The B-H bond of typical boranes is heterolytically split by the polar Ru-S bond of a tethered ruthenium(II) thiolate complex, affording a ruthenium(II) hydride and borenium ions with a dative interaction with the sulfur atom. These stable adducts were spectroscopically characterized, and in one case, the B-H bond activation step was crystallographically verified, a snapshot of the σ-bond metathesis

  典型硼烷的 BH 键被束缚的钌 (II) 硫醇盐络合物的极性 Ru-S 键异裂，提供氢化钌 (II) 和硼离子，并与硫原子发生配价相互作用。这些稳定的加合物经过光谱表征，在一种情况下，BH 键激活步骤在晶体学上得到验证，这是 σ 键复分解的快照。源自 9-硼双环 [3.3.1] 壬烷二聚体 [(9-BBN)2]、频哪醇硼烷 (pinBH) 和儿茶酚硼烷 (catBH) 的硼离子允许吲哚的亲电芳香取代。针对各种氮杂环进一步阐述了前所未有的 pinB 阳离子亲电硼酸化。
• Halogenation of Indoles with Copper(II) Halides: Selective Synthesis of 2-Halo-, 3-Halo-, and 2,3-Dibromoindoles
  作者：Jin-Heng Li、Nai-Xing Wang、Shi Tang、Ye-Xiang Xie

  DOI：10.1055/s-2007-966030

  日期：——

  A simple and selective protocol for the halogenation of indoles with copper(II) bromide or chloride to synthesize 2-halo-, 3- halo-, and 2,3-dibromoindoles was developed. It was found that both base and water could be used as switches for the selectivity of the halogenation reactions. In the presence of copper(II) halide and sodium hydroxide, 3-haloindoles were obtained as the major prod- ucts, whereas

  开发了一种用溴化铜 (II) 或氯化铜卤化吲哚​​以合成 2-卤代、3-卤代和 2,3-二溴吲哚的简单且选择性的方案。发现碱和水都可以用作卤化反应选择性的开关。在卤化铜 (II) 和氢氧化钠存在的情况下，主要产物是 3-卤代吲哚，而当加入水而不是氢氧化钠时，选择性转向 2,3-二卤代吲哚。此外，在标准条件下，3-取代吲哚的 2-卤化也以中等至良好的产率成功进行。
• Cooperative Catalytic Activation of Si−H Bonds by a Polar Ru−S Bond: Regioselective Low-Temperature C−H Silylation of Indoles under Neutral Conditions by a Friedel−Crafts Mechanism
  作者：Hendrik F. T. Klare、Martin Oestreich、Jun-ichi Ito、Hisao Nishiyama、Yasuhiro Ohki、Kazuyuki Tatsumi

  DOI：10.1021/ja111483r

  日期：2011.3.16

  Merging cooperative Si-H bond activation and electrophilic aromatic substitution paves the way for C-3-selective indole C-H functionalization under electronic and not conventional steric control. The Si-H bond is heterolytically split by the Ru-S bond of a coordinatively unsaturated cationic ruthenium(II) complex, forming a sulfur-stabilized silicon electrophile. The Wheland intermediate of the subsequent

  合并协同的 Si-H 键活化和亲电芳香取代为在电子而非传统空间控制下的 C-3 选择性吲哚 CH 官能化铺平了道路。Si-H 键被配位不饱和阳离子钌 (II) 配合物的 Ru-S 键异裂，形成硫稳定的硅亲电试剂。假设随后的 Friedel-Crafts 型过程的 Wheland 中间体被硫原子去质子化，不需要添加碱。整个催化过程在低温下无需溶剂，仅释放二氢。
• Synthesis and Preliminary Biological Studies of 3-Substituted Indoles Accessed by a Palladium-Catalyzed Enantioselective Alkene Difunctionalization Reaction
  作者：Tejas P. Pathak、Keith M. Gligorich、Bryan E. Welm、Matthew S. Sigman

  DOI：10.1021/ja103472a

  日期：2010.6.16

  A unique alkene difunctionalization reaction that allows rapid construction of molecular complexity around the biologically relevant indole framework has been developed. The reaction proceeds with up to 87% yield, 99:1 er, and >20:1 dr. Evaluation of several of the compounds revealed promising anticancer activity against MCF-7 cells.

  已经开发出一种独特的烯烃双官能化反应，可以在生物相关的吲哚框架周围快速构建分子复杂性。反应以高达 87% 的产率、99:1 er 和 >20:1 dr 进行。对几种化合物的评估揭示了对 MCF-7 细胞的有希望的抗癌活性。