1-[3-(3-trifluoromethyl-phenyl)-prop-2-ynyl]-1H-indole-2-carbaldehyde | 600727-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[3-(3-trifluoromethyl-phenyl)-prop-2-ynyl]-1H-indole-2-carbaldehyde
• 英文别名: 1-[3-[3-(Trifluoromethyl)phenyl]prop-2-ynyl]indole-2-carbaldehyde；1-[3-[3-(trifluoromethyl)phenyl]prop-2-ynyl]indole-2-carbaldehyde
• CAS: 600727-42-2
• 化学式: C₁₉H₁₂F₃NO
• 分子量: 327.306
• InChiKey: IHXJDAIPSTWBTR-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  466.6±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[3-(3-trifluoromethyl-phenyl)-prop-2-ynyl]-1H-indole-2-carbaldehyde 在 氨 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以90%的产率得到3-(3-trifluoromethyl-benzyl)-pyrazino[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：

  3-碘三氟甲苯 、 1-(prop-2-yn-1-yl)-1H-indole-2-carbaldehyde 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到1-[3-(3-trifluoromethyl-phenyl)-prop-2-ynyl]-1H-indole-2-carbaldehyde
  参考文献：
  名称：

  Novel intramolecular cyclization of N-alkynyl heterocycles containing proximate nucleophiles

  摘要：

  Intramolecular cyclization of 2-acyl-l-propargyl-1H-indoles in the presence of ammonia provides an easy entry to pyrazino[1,2-a]indole nucleus. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01202-4

文献信息

• Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles: a new entry to [1,4]oxazino[4,3-a]indoles
  作者：Giorgio Abbiati、Valentina Canevari、Solange Caimi、Elisabetta Rossi

  DOI：10.1016/j.tetlet.2005.08.102

  日期：2005.10

  The unusual [1,4]oxazino[4,3-a]indole nucleus was prepared, under mild reaction conditions, by reacting 1-alkynyl-1H-indole-2-carbaldehydes with various alkoxides, generated in situ from the corresponding alkyl, benzyl, allyl and propargyl alcohols. (c) 2005 Elsevier Ltd. All rights reserved.