1-acetyl-3-ethyl-2-methyl-1H-indole | 145568-54-3

• 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-acetyl-3-ethyl-2-methyl-1H-indole
• 英文别名: 1-(3-ethyl-2-methylindol-1-yl)ethanone
• CAS: 145568-54-3
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: FPHAWFPIGXMURG-UHFFFAOYSA-N

物化性质

• 沸点：
  316.4±11.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-acetyl-3-ethyl-2-methyl-1H-indole 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.5h， 生成 1-(3-Ethyl-3-hydroxy-2-methylene-2,3-dihydro-indol-1-yl)-ethanone
  参考文献：
  名称：

  Dimethyldioxirane oxidation of indole derivatives. Formation of novel indole-2,3-epoxides and a versatile synthetic route to indolinones and indolines

  摘要：

  DOI：

  10.1021/ja00072a061
• 作为产物：
  描述：

  C₁₃H₁₆INO 在 palladium diacetate 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以62%的产率得到1-acetyl-3-ethyl-2-methyl-1H-indole
  参考文献：
  名称：

  10.1134/s107036321302028x

  摘要：

  DOI：

  10.1134/s107036321302028x

文献信息

• 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.
• Reactions of N-acylated indoles with singlet oxygen
  作者：Xiaojun Zhang、Christopher S. Foote、Saeed I. Khan

  DOI：10.1021/jo00053a014

  日期：1993.1

  Reactions of seven N-acyl indole derivatives with singlet oxygen have been investigated. 1-Acetyl-(1a) and 1-(chloroacetyl)-2,3-dimethylindole (1b) gave exclusively 1-acetyl-(2a) and 1-(chloroacetyl)-2-hydroperoxy-3-methyleneindoline (2b), respectively, in high yields via ene reaction on irradiation with oxygen in the presence of TPP sensitizer. 1-Acetyl-3-methylindole (1c) gave only 1-acetyl-2-hydroperoxy-3-methyleneindoline (2c) in low yield under the same conditions. In contrast, 1-acetyl-2-methyl-3-ethylindole (3a) and 1-acetyl-2-methyl-3-isopropylindole (3b) gave a mixture of ene products, 2-hydroperoxy- and 3-hydroperoxyindolines (4a and b and 5a and b), in addition to 2,3-bond cleavage products 6a and 6b, respectively. In the case of 1-acetyl-2-methyl-3-tert-butylindole (7), only the product of 2,3-bond cleavage (8) was obtained. A 1,2-dioxetane is intermediate in the cleavage and could be observed after photooxygenation of 7 at -5-degrees-C by NMR and was reduced by trimethylphosphite and dimethyl sulfide. The decomposition rate constant of 1,2-dioxetane 10 was measured by NMR; E(a) is 24.6 kcal/mol.
• 1,2-Dioxetane formation in photooxygenation of N-acylated indole derivatives
  作者：Xiaojun Zhang、Christopher S. Foote

  DOI：10.1021/jo00072a042

  日期：1993.9

  Eight N-acylated indole derivatives (1a-h) react with singlet oxygen at low temperature (-5 to -78-degrees-C) in methanol-d4 or methanol-d4-methylene chloride-d2 to afford 1,2-dioxetanes 2a-h, whose structures are characterized by low-temperature C-13 NMR and H-1 NMR spectra and chemical transformations. These strained 1,2-dioxetanes decompose smoothly and exclusively to dicarbonyl cleavage products 3a-h upon warming to room temperature.
• Dimethyldioxirane oxidation of indole derivatives. Formation of novel indole-2,3-epoxides and a versatile synthetic route to indolinones and indolines
  作者：Xiaojun Zhang、Christopher S. Foote

  DOI：10.1021/ja00072a061

  日期：1993.9
• 10.1134/s107036321302028x
  作者：Skladchikov、Gataullin

  DOI：10.1134/s107036321302028x

  日期：——