1-{1-[3-(4-chlorophenyl)-prop-2-ynyl]-1H-indol-2-yl}ethanone | 600727-37-5

• 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-{1-[3-(4-chlorophenyl)-prop-2-ynyl]-1H-indol-2-yl}ethanone
• 英文别名: 1-[3-(4-chlorophenyl)-prop-2-ynyl]-2-acetyl-1H-indole；1-[1-[3-(4-Chlorophenyl)prop-2-ynyl]indol-2-yl]ethanone
• CAS: 600727-37-5
• 化学式: C₁₉H₁₄ClNO
• 分子量: 307.779
• InChiKey: MIRBLTZLZXFCJI-UHFFFAOYSA-N

物化性质

• 熔点：
  107-109 °C
• 沸点：
  486.6±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 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：
  1

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 1-{1-[3-(4-chlorophenyl)-prop-2-ynyl]-1H-indol-2-yl}ethanone 在 gallium(III) trichloride 作用下， 以 甲苯 为溶剂， 以87%的产率得到7-(4-chlorobenzyl)-9-(pyrrolidin-1-yl)pyrido[1,2-a]indole
  参考文献：
  名称：

  路易斯酸介导的δ-酮炔的氨基苯环化反应：1-氨基咔唑和9-氨基吡啶并[1,2-a]吲哚的合成

  摘要：

  2-酰基-N-炔丙基吲哚1和2-酰基-3-炔丙基吲哚5在适当的路易斯酸存在下与吡咯烷发生氨基苯并化反应，得到9-氨基吡啶并[1,2-a]吲哚6和1-氨基咔唑7，分别。选择合适的路易斯酸，TiCl4 或 GaCl3 为 1，InCl3 为 5，允许多米诺骨牌过程涉及初始形成烯胺中间体，然后区域选择性 6-exo-dig 分子内亲核攻击不饱和的亲核末端系统（烯氨基部分的β-碳）连接到碳-碳三键。此外，还报告了有关反应机理和两种催化剂作用的几个特征，以及反应炔烃的电子性质。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900039
• 作为产物：
  描述：

  2-乙酰基吲哚 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 7.0h， 生成 1-{1-[3-(4-chlorophenyl)-prop-2-ynyl]-1H-indol-2-yl}ethanone
  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

• Novel intramolecular cyclization of N-alkynyl heterocycles containing proximate nucleophiles
  作者：Giorgio Abbiati、Antonio Arcadi、Egle Beccalli、Elisabetta Rossi

  DOI：10.1016/s0040-4039(03)01202-4

  日期：2003.7

  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.
• 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.
• Lewis Acid Mediated Aminobenzannulation Reactions of δ-Ketoalkynes: Synthesis of 1-Aminocarbazoles and 9-Aminopyrido[1,2-<i>a</i>]indoles
  作者：Diego Facoetti、Giorgio Abbiati、Elisabetta Rossi

  DOI：10.1002/ejoc.200900039

  日期：2009.6

  2-Acyl-N-propargylindoles 1 and 2-acyl-3-propargylindoles 5 undergo aminobenzannulation reactions with pyrrolidine in the presence of an appropriate Lewis acid to give 9-aminopyrido[1,2-a]indoles 6 and 1-aminocarbazoles 7, respectively. The selection of the appropriate Lewis acid, TiCl4 or GaCl3 for 1 and InCl3 for 5, allows the domino process involving the initial formation of an enamine intermediate

  2-酰基-N-炔丙基吲哚1和2-酰基-3-炔丙基吲哚5在适当的路易斯酸存在下与吡咯烷发生氨基苯并化反应，得到9-氨基吡啶并[1,2-a]吲哚6和1-氨基咔唑7，分别。选择合适的路易斯酸，TiCl4 或 GaCl3 为 1，InCl3 为 5，允许多米诺骨牌过程涉及初始形成烯胺中间体，然后区域选择性 6-exo-dig 分子内亲核攻击不饱和的亲核末端系统（烯氨基部分的β-碳）连接到碳-碳三键。此外，还报告了有关反应机理和两种催化剂作用的几个特征，以及反应炔烃的电子性质。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)