1-propargyl-2-acetylindole | 600727-36-4

• 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-propargyl-2-acetylindole
• 英文别名: 2-acetyl-1-propargyl-1H-indole；1-(1-prop-2-ynyl-1H-indol-2-yl)ethanone；2-acetyl-1-propargylindole；1-(1-Prop-2-ynylindol-2-yl)ethanone
• CAS: 600727-36-4
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: CWMDTFNJAOBFPT-UHFFFAOYSA-N

物化性质

• 熔点：
  98-101 °C
• 沸点：
  350.6±22.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-propargyl-2-acetylindole 在 四氯化钛 叔丁胺 作用下， 以 甲苯 为溶剂， 反应 0.3h， 以50%的产率得到1-methyl-3H-pyrrolo[1,2-a]indole-2-carbaldehyde
  参考文献：
  名称：

  TiCl₄/t-BuNH₂-Promoted Hydroamination/Annulation of δ-Keto-acetylenes:  Synthesis of Novel Pyrrolo[1,2-a]indol-2-carbaldehydes

  摘要：

  [GRAPHICS]An original TiCl4/t-BuNH2-mediated hydroamination/annulation domino reaction of delta-keto-acetylenes is described. The synthesis of pyrrolo[ 1,2-a] indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles runs under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multiactivity reagent: catalyst/Lewis acid/water scavenger. Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.

  DOI：

  10.1021/ol061872u
• 作为产物：
  描述：

  2-乙酰基吲哚 、 3-溴丙炔 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 水 、 甲苯 为溶剂， 以98%的产率得到1-propargyl-2-acetylindole
  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

文献信息

• Nickel(II)-Catalyzed [5 + 1] Annulation of 2-Carbonyl-1-propargylindoles with Hydroxylamine To Synthesize Pyrazino[1,2-<i>a</i>]indole-2-oxides in Water
  作者：Hong-Yan Bi、Min Du、Cheng-Xue Pan、Yuhong Xiao、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1021/acs.joc.9b00784

  日期：2019.8.16

  the efficient synthesis of various pyrazino[1,2-a]indole-2-oxides was developed through a nickel(II)-catalyzed [5 + 1] annulation of 2-carbonyl-1-propargylindoles with hydroxylamine in water without using an organic solvent. The reaction involved an initial condensation of 2-carbonyl-1-propargylindoles with hydroxylamine to afford oxime intermediates, which then underwent a nickel(II)-catalyzed 6-exo-dig

  通过镍（II）催化的2-羰基-1-炔丙基吲哚的[5 +1]环化反应，开发了一种原子经济实用的方法，可有效合成各种吡嗪并[1,2 - a ]吲哚-2-氧化物。在不使用有机溶剂的情况下与羟胺一起使用。该反应涉及2-羰基-1-炔丙基吲哚与羟胺的初始缩合以提供肟中间体，然后将其进行镍（II）催化的6-exo-dig环化。初步研究表明（n -Bu）4NI用作相转移催化剂，并促进了活性镍（II）物种的形成。更重要的是，镍（II）盐和水中的相转移催化剂可以循环使用七次，并且通过过滤和洗涤方案可以容易地以高收率获得克级可缩放产品。
• Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino [1,2-a] indoles
  作者：Rakesh Kumar Tiwari、Devender Singh、Jaspal Singh、Vibha Yadav、Ajay K. Pathak、Rajesh Dabur、Anil K. Chhillar、Rambir Singh、G.L. Sharma、Ramesh Chandra、Akhilesh K. Verma

  DOI：10.1016/j.bmcl.2005.09.066

  日期：2006.1

  A series of substituted 1,2,3,4-tetrahydropyrazino [1,2-a] indole derivatives have been synthesized and tested against the Gram positive and Gram negative strains of bacteria namely Staphylococcus aureus (MTCCB 737), Salmonella typhi (MTCCB 733), Pseudomonas aeruginosa (MTCCB 741), Streptomyces thermonitrificans (MTCCB 1824) and Escherichia coli (MTCCB 1652). All synthesized compounds showed mild to moderate activity. However, compounds 4d-f were found to have potent activity against pathogenic bacteria used in the study. Their MIC ranged from 3.75 to 60 mu g/disc. In vitro toxicity tests demonstrated that toxicity of 4d-f was not significantly different than that of gentamycin. However, at higher concentration (1000-4000 mu g/ml) difference was highly significant. (c) 2005 Elsevier 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.
• 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.