1-methyl-2,3-dipropyl-1H-indole | 135224-93-0

• 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-dipropyl-1H-indole
• 英文别名: 1-Methyl-2,3-dipropylindole
• CAS: 135224-93-0
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: DZUZANCHOATTNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-甲基-N-亚硝基苯胺 在 [RhCl2(p-cymene)]2 、 zinc trifluoromethanesulfonate 、 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 1-methyl-2,3-dipropyl-1H-indole
  参考文献：
  名称：

  钌（II）催化的N-N键作为内部氧化剂的无痕CH功能化

  摘要：

  据报道，一种以前难以捉摸的Ru II催化的基于N-N键的无痕CH功能化策略。N-氨基（即肼）用于炔烃或烯烃的定向C H官能化，提供吲哚衍生物或烯化产物。该合成具有广泛的底物范围，优越的原子和步骤经济性以及温和的反应条件。

  DOI：

  10.1002/chem.201602936

文献信息

• One-Pot Tandem <i>ortho</i>-Naphthoquinone-Catalyzed Aerobic Nitrosation of <i>N</i>-Alkylanilines and Rh(III)-Catalyzed C–H Functionalization Sequence to Indole and Aniline Derivatives
  作者：Tengda Si、Hun Young Kim、Kyungsoo Oh

  DOI：10.1021/acs.joc.0c02776

  日期：2021.1.1

  The nitroso group served as a traceless directing group for the C–H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the

  亚硝基基团是N-烷基苯胺C–H官能化的无痕导向基团，在用作内部氧化剂或在随后的还原条件下最终被除去。o- NQ催化剂无需使用溶剂和化学计量的氧化剂即可好氧氧化N-烷基苯胺的独特能力，为开发伸缩式催化剂系统提供了新的机会，而无需直接处理危险的N-亚硝基化合物。
• Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles
  作者：Shuguang Zhou、Jinhu Wang、Lili Wang、Kehao Chen、Chao Song、Jin Zhu

  DOI：10.1021/acs.orglett.6b01805

  日期：2016.8.5

  Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C–H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of

  本文报道了Co（III）催化的，内部和末端炔烃相容的吲哚合成方案。的Ñ -氨基（肼）基团面授不同的，多样化反应性模式用于定向C-H官能化/环化反应。显着的合成特征包括对间取代的芳基肼的区域选择性，对链支化的末端炔烃的区域选择性，在C2硅烷化的吲哚衍生物上通过C2-去甲硅烷基化正式引入炔属单元，通过连续的C3-衍生化和C2对区域选择性进行正式转化-去甲硅烷基化过程，以及线性链末端炔烃的形式键迁移。
• Rhodium(III)-catalyzed synthesis of indoles from 1-alkylidene-2-arylhydrazines and alkynes via C–H and N–N bond cleavages
  作者：Takanori Matsuda、Yuki Tomaru

  DOI：10.1016/j.tetlet.2014.04.016

  日期：2014.5

  1-Alkylidene-2-arylhydrazines undergo annulative coupling with internal alkynes in the presence of a rhodium(III) catalyst and a copper(II) salt. The reaction proceeds through cleavage of the C–H and N–N bonds of hydrazines to afford 1,2,3-trisubstituted indole derivatives.

  1-炔基-2-芳基肼在铑（III）催化剂和铜（II）盐存在下与内部炔烃进行环状偶联。通过肼的CH键和NH键的裂解进行反应，得到1,2,3-三取代的吲哚衍生物。
• Nickel-catalyzed Decarbonylative and Decarboxylative Cycloaddition of Isatoic Anhydrides with Alkynes
  作者：Kenichiro Nakai、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.130578

  日期：2013.10.5

  We have developed a nickel-catalyzed cycloaddition of isatoic anhydrides with alkynes to afford 2,3-disubstituted indoles. The reaction proceeds via the elimination of carbon monoxide and carbon dioxide and the insertion of alkynes.

  我们开发了一种镍催化的异酸酐与炔烃的环加成反应，从而得到 2,3-二取代吲哚。该反应通过消除一氧化碳和二氧化碳以及插入炔烃进行。
• 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.