phenyl[1-(3-phenylprop-2-ynyl)-1H-indol-2-yl]methanone | 853052-26-3

• 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: phenyl[1-(3-phenylprop-2-ynyl)-1H-indol-2-yl]methanone
• 英文别名: Phenyl-[1-(3-phenylprop-2-ynyl)indol-2-yl]methanone
• CAS: 853052-26-3
• 化学式: C₂₄H₁₇NO
• 分子量: 335.405
• InChiKey: DWKQSGYZLUBDRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  phenyl[1-(3-phenylprop-2-ynyl)-1H-indol-2-yl]methanone 在 氨 、 四氯化钛 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以82%的产率得到1-phenyl-3-[1-phenyl-(Z)-methylidene]-3,4-dihydropyrazino[1,2-a]indole
  参考文献：
  名称：

  Intramolecular Cyclization of δ-Iminoacetylenes:  A New Entry to Pyrazino[1,2-a]indoles

  摘要：

  The synthesis of the pyrazino[1,2-alpha]indole nucleus was achieved by intramolecular cyclization of several 2-carbonyl-1-propargylindoles in the presence of ammonia. The reaction conditions were optimized using microwave heating and a pool of catalysts. Cyclization of 1-alkynylindole-2-carbaldehydes was easily accomplished under standard heating conditions, whereas microwave heating contributed to reduced reaction times and improved overall yields. Moreover, a fine-tuning of the microwave irradiation time made possible the selective synthesis of both pyrazino[1,2-alpha]indole isomers. TiCl4 proved the catalytic system of choice to achieve pyrazinoindoles in satisfactory yields starting from 1-alkynyl-2-acetylindoles and 1-alkynyl-2-benzoylindole derivatives. Also in these cases, microwave heating contributed to faster reactions and improved yields. The uncatalyzed versus catalyzed reaction mechanism is discussed.

  DOI：

  10.1021/jo0502246
• 作为产物：
  描述：

  1H-吲哚-2-基(苯基)甲酮 在 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.5h， 生成 phenyl[1-(3-phenylprop-2-ynyl)-1H-indol-2-yl]methanone
  参考文献：
  名称：

  Intramolecular Cyclization of δ-Iminoacetylenes:  A New Entry to Pyrazino[1,2-a]indoles

  摘要：

  The synthesis of the pyrazino[1,2-alpha]indole nucleus was achieved by intramolecular cyclization of several 2-carbonyl-1-propargylindoles in the presence of ammonia. The reaction conditions were optimized using microwave heating and a pool of catalysts. Cyclization of 1-alkynylindole-2-carbaldehydes was easily accomplished under standard heating conditions, whereas microwave heating contributed to reduced reaction times and improved overall yields. Moreover, a fine-tuning of the microwave irradiation time made possible the selective synthesis of both pyrazino[1,2-alpha]indole isomers. TiCl4 proved the catalytic system of choice to achieve pyrazinoindoles in satisfactory yields starting from 1-alkynyl-2-acetylindoles and 1-alkynyl-2-benzoylindole derivatives. Also in these cases, microwave heating contributed to faster reactions and improved yields. The uncatalyzed versus catalyzed reaction mechanism is discussed.

  DOI：

  10.1021/jo0502246

文献信息

• Intramolecular Cyclization of δ-Iminoacetylenes:  A New Entry to Pyrazino[1,2-<i>a</i>]indoles
  作者：Giorgio Abbiati、Antonio Arcadi、Alessandra Bellinazzi、Egle Beccalli、Elisabetta Rossi、Simona Zanzola

  DOI：10.1021/jo0502246

  日期：2005.5.1

  The synthesis of the pyrazino[1,2-alpha]indole nucleus was achieved by intramolecular cyclization of several 2-carbonyl-1-propargylindoles in the presence of ammonia. The reaction conditions were optimized using microwave heating and a pool of catalysts. Cyclization of 1-alkynylindole-2-carbaldehydes was easily accomplished under standard heating conditions, whereas microwave heating contributed to reduced reaction times and improved overall yields. Moreover, a fine-tuning of the microwave irradiation time made possible the selective synthesis of both pyrazino[1,2-alpha]indole isomers. TiCl4 proved the catalytic system of choice to achieve pyrazinoindoles in satisfactory yields starting from 1-alkynyl-2-acetylindoles and 1-alkynyl-2-benzoylindole derivatives. Also in these cases, microwave heating contributed to faster reactions and improved yields. The uncatalyzed versus catalyzed reaction mechanism is discussed.