1-(2-methyl-propenyl)-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: 1-(2-methyl-propenyl)-1H-indole
• 英文别名: 1-(2-Methylpropenyl)indole；1-(2-Methylprop-1-enyl)indole
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: QLFKODGIRPNZCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-(2-methyl-propenyl)-1H-indole 在 Pt-loaded HBEA 作用下， 以 邻二甲苯 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 1-isobutyl-1H-indole
  参考文献：
  名称：

  使用Pt / HBEA催化剂将伯醇与吲哚选择性地进行N-烷基化

  摘要：

  负载铂的HBEA（H +交换的BEA沸石）被发现是一种有效且可重复使用的非均相催化剂，用于在借用氢方法的驱动下在无添加剂的条件下用脂肪族和苄基伯醇对吲哚进行区域选择性N-烷基化。结构和机理研究表明，Pt金属簇上的Pt 0位点和沸石的Brønsted酸位点是一种协同机制，其中Pt 0位点负责脱氢/氢化步骤，而Brønsted酸位点负责区域选择性缩合将带有醛的吲哚制成烯胺中间体。

  DOI：

  10.1039/c4gc01419g
• 作为产物：
  描述：

  1H-吲哚,锂盐 、 1-chloro-2-methyl-1-(p-tolylsulfinyl)-1-propene 在 magnesium,2-methylpropane,bromide 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 甲苯 、 乙醚 为溶剂， 以46%的产率得到1-(2-methyl-propenyl)-1H-indole
  参考文献：
  名称：

  Direct N- and C-alkenylation of nitrogen-containing heterocycles with magnesium alkylidene carbenoids

  摘要：

  Treatment of magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides with isopropylmagnesium chloride at -78 degrees C in toluene, with N-lithio nitrogen-containing heterocycles gave N-alkenylated products in moderate to good yields. Also, the reaction of C-lithio indoles, which were generated from N-protected indoles, with magnesium alkylidene carbenoids gave C-2 or C-3 alkenylated products, corresponding to the protective group. The intermediate of these reactions were found to be the alkenyl anion, which could be trapped with electrophiles to give the heterocycles having fully substituted alkenes. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.072

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• A novel direct N-alkenylation of nitrogen-containing heterocycles with magnesium alkylidene carbenoids
  作者：Tsuyoshi Satoh、Jo Sakurada、Yumi Ogino

  DOI：10.1016/j.tetlet.2005.05.058

  日期：2005.7

  Treatment of magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides with isopropylmagnesium chloride at −78 °C in toluene, with N-lithio nitrogen-containing heterocycles (e.g., indole, indazole, phenothiazine, and phenoxazine) gave N-alkenylated products in moderate to good yields. The intermediate of this reaction was found to be the alkenyl anion, which could

  在异丙基氯化镁中，于-78°C在甲苯中，用N-硫代含氮杂环（例如，吲哚，吲唑，吩噻嗪和吩恶嗪）处理1-氯乙烯基对甲苯基亚砜生成的亚烷基镁类胡萝卜素，得到N链烯基化产物，产率中等至良好。发现该反应的中间体是烯基阴离子，其可以使用CuI作为催化剂用碘代烷烃捕获，以在氮上得到具有完全取代的烯烃的杂环。烯基阴离子中间体也可以被苯甲酰氯和异氰酸苯酯捕集。该反应提供了含氮杂环的相当新颖和直接的N-烯基化。
• Copper-catalyzed formation of carbon heteroatom and carbon-carbon bonds
  申请人：Buchwald L. Stephen

  公开号：US20050215794A1

  公开（公告）日：2005-09-29

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和酰胺或胺基团的氮原子之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和酰肼的氮原子之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和含氮杂环芳香族化合物（例如吲哚、吡唑和吲唑）的氮原子之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和醇的氧原子之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子（例如烯醇酸根离子或马隆酸根离子）的反应物和苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价易行。
• COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP1390340A1

  公开（公告）日：2004-02-25
• EP1390340A4
  申请人：——

  公开号：EP1390340A4

  公开（公告）日：2007-07-25