1-methyl-2-(3-nitrophenyl)-1H-indole | 1018914-51-6

• 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-methyl-2-(3-nitrophenyl)-1H-indole
• 英文别名: 1-Methyl-2-(3-nitrophenyl)indole
• CAS: 1018914-51-6
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: WQSXVCSJENUVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 1-碘-3-硝基苯 在 水 、 palladium diacetate 、 silver cyclohexanecarboxylate 作用下， 反应 16.0h， 以91%的产率得到1-methyl-2-(3-nitrophenyl)-1H-indole
  参考文献：
  名称：

  “在水上”，无磷的钯催化的室温C ？吲哚的H化

  摘要：

  掌握化学反应！一个“水”，钯-催化的，游离的膦直接Ç  ħ吲哚的在25-30℃的芳基化，与iodoarenes，公开了（参见方案; TBDMS = ñ -叔丁基二甲基醚; SEM = Ñ -2 -（三甲基甲硅烷基）乙氧基甲基; Bn =苄基，Piv =吡巴贝基）。反应条件温和性使得各种N1的宽容-保护的吲哚类化合物。

  DOI：

  10.1002/chem.201302838

文献信息

• Direct C–H bond activation: palladium-on-carbon as a reusable heterogeneous catalyst for C-2 arylation of indoles with arylboronic acids
  作者：Prantika Bhattacharjee、Purna K Boruah、Manash R Das、Utpal Bora

  DOI：10.1039/d0nj00735h

  日期：——

  functionalization of indoles with arylboronic acids is achieved using palladium supported on carbon as a reusable heterogeneous catalyst in the presence of an oxidant under mild conditions. The current protocol formed exclusive C-2 selective products without the aid of any ligand or directing group. The catalyst is reusable for up to four catalytic cycles with the retention of catalytic efficiency.

  在温和条件下，在氧化剂存在下，使用负载在碳上的钯作为可重复使用的多相催化剂，可以实现吲哚与芳基硼酸的直接C（sp 2）–H键官能化。目前的方案在没有任何配体或指导基团的帮助下形成了排他的C-2选择性产物。该催化剂可重复使用多达四个催化循环，同时保持催化效率。
• “On Water”, Phosphine-Free Palladium-Catalyzed Room Temperature CH Arylation of Indoles
  作者：Saidul Islam、Igor Larrosa

  DOI：10.1002/chem.201302838

  日期：2013.11.4

  top of your chemistry! An “on water”, palladium‐catalyzed, phosphine‐free direct CH arylation of indoles, with iodoarenes at 25–30 °C, is disclosed (see scheme; TBDMS=N‐tert‐butyldimethylsilyl ether; SEM=N‐2‐(trimethylsilyl)ethoxymethyl; Bn=benzyl, Piv=pivabyl). The mildness of the reaction conditions permits the tolerance of a variety of N1‐protected indoles.

  掌握化学反应！一个“水”，钯-催化的，游离的膦直接Ç  ħ吲哚的在25-30℃的芳基化，与iodoarenes，公开了（参见方案; TBDMS = ñ -叔丁基二甲基醚; SEM = Ñ -2 -（三甲基甲硅烷基）乙氧基甲基; Bn =苄基，Piv =吡巴贝基）。反应条件温和性使得各种N1的宽容-保护的吲哚类化合物。
• Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium
  作者：Woen Susanto、Chi-Yuan Chu、Wei Jie Ang、Tzyy-Chao Chou、Lee-Chiang Lo、Yulin Lam

  DOI：10.1021/jo202482h

  日期：2012.3.16

  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 a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.
• Palladium-Catalyzed Direct Arylation of (Hetero)Arenes with Aryl Boronic Acids
  作者：Shang-Dong Yang、Chang-Liang Sun、Zhao Fang、Bi-Jie Li、Yi-Zhou Li、Zhang-Jie Shi

  DOI：10.1002/anie.200704619

  日期：2008.2.8
• Palladium catalyzed direct C-2 arylation of indoles
  作者：Jie Feng、Guoping Lu、Meifang Lv、Chun Cai

  DOI：10.1016/j.jorganchem.2014.02.017

  日期：2014.7

  The synthesis and catalytic evaluation of palladium complexes containing NCN Pincer ligand is reported. The pincer palladium complexes as (pre)catalyst showed efficient catalytic activity for the C–H arylation of N-substituted indoles, allowing the synthesis of 2-arylindoles with moderate to good yields and excellent regioselectivities.

  报道了含NCN Pincer配体的钯配合物的合成和催化评估。夹心钯配合物作为（预）催化剂对N取代的吲哚的CH芳基化反应显示出有效的催化活性，从而以中等至良好的收率和优异的区域选择性合成了2-芳基吲哚。