phenyl(1-prop-2-ynyl-1H-indol-2-yl)methanone | 853052-23-0

• 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-prop-2-ynyl-1H-indol-2-yl)methanone
• 英文别名: 1-propargyl-2-benzoylindole；Phenyl-(1-prop-2-ynylindol-2-yl)methanone
• CAS: 853052-23-0
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: BDYIQXSBLPQDCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  437.1±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-prop-2-ynyl-1H-indol-2-yl)methanone 在 四(三苯基膦)钯 copper(l) iodide 、 氨 、 四氯化钛 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.22h， 生成 3-[1-(4-methoxy-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：

  2,2-dimethoxy-1-(phenyl)ethanol 在 盐酸 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 20.0~90.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 phenyl(1-prop-2-ynyl-1H-indol-2-yl)methanone
  参考文献：
  名称：

  用于区域选择性合成酰吲哚的间断海恩斯重排方法

  摘要：

  已经实现了从邻酰基苯胺和α-羟基羰基或其等价物合成2-和3-酰基吲哚的有效且通用的方法，具有高区域选择性。该策略涉及分子内捕获原位生成的氨基烯醇中间体和中断的海恩斯重排途径，然后进行芳构化或重排/芳构化。重要特征包括优异的区域控制、良好的官能团耐受性、操作简单性以及应用于克级合成和抗肿瘤剂的合成。

  DOI：

  10.1039/d3cc04144a

文献信息

• 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.
• TiCl₄/<i>t</i>-BuNH₂-Promoted Hydroamination/Annulation of δ-Keto-acetylenes:  Synthesis of Novel Pyrrolo[1,2-<i>a</i>]indol-2-carbaldehydes
  作者：Giorgio Abbiati、Alessandro Casoni、Valentina Canevari、Donatella Nava、Elisabetta Rossi

  DOI：10.1021/ol061872u

  日期：2006.10.1

  [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.