1-(氯乙酰基)-2,3-二甲基吲哚 | 66624-39-3

• 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
• 中文名称: 1-(氯乙酰基)-2,3-二甲基吲哚
• 英文名称: 1-(Chloroacetyl)-2,3-dimethylindole
• 英文别名: 1-Chloracetyl-2,3-dimethyl-indol；1-(Chloroacetyl)-2,3-dimethyl-1H-indole；2-chloro-1-(2,3-dimethylindol-1-yl)ethanone
• CAS: 66624-39-3
• 化学式: C₁₂H₁₂ClNO
• mdl: MFCD02237249
• 分子量: 221.686
• InChiKey: ATOQMVQNVWIOOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(氯乙酰基)-2,3-二甲基吲哚 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 7.0h， 生成 1-(chloroacetyl)-3,3-dimethyl-2-indolinone
  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：

  2,3-二甲基吲哚 、 氯乙酰氯 生成 1-(氯乙酰基)-2,3-二甲基吲哚
  参考文献：
  名称：

  Reactions of N-acylated indoles with singlet oxygen

  摘要：

  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.

  DOI：

  10.1021/jo00053a014

文献信息

• Über lokalanästhetisch und antiarrhythmisch wirksame Indol- und Indolin-Derivate, 1. Mitt. Darstellung von 1-, 2- und 3-Aminoacetyl-indolen sowie 1-Aminoacetylindolinen
  作者：Ernst Mutschler、Werner Winkler

  DOI：10.1002/ardp.19783110311

  日期：——

  Verschiedene Indole und Indoline wurden mit Chloressigsäure‐Derivaten umgesetzt und die entstandenen Chloracetyl‐Verbindungen mit Aminen zur Reaktion gebracht.

  各种吲哚和二氢吲哚与氯乙酸衍生物反应，所得氯乙酰化合物与胺反应。
• 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.
• MUTSCHLER E.; WINKLER W., ARCH. PHARM., 1978, 311, NO 3, 248-255
  作者：MUTSCHLER E.、 WINKLER W.

  DOI：——

  日期：——
• 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.
• 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