3-(5-nitro-1H-indol-3-yl)-3-oxopropanenitrile | 1363843-81-5

• 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: 3-(5-nitro-1H-indol-3-yl)-3-oxopropanenitrile
• CAS: 1363843-81-5
• 化学式: C₁₁H₇N₃O₃
• 分子量: 229.195
• InChiKey: JFXFXRIYXBUOSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-nitro-1H-indol-3-yl)-3-oxopropanenitrile 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.5h， 生成 1-(5-硝基-1H-吲哚-3-基)乙酮
  参考文献：
  名称：

  Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst

  摘要：

  报道了一种利用5%氢氧化钠水溶液，将3-氰基乙酰基吲哚2(a-e)高效转化为3-乙酰基吲哚3(a-e)的简便方法。四丁基溴化铵（TBAB）被发现是一种有效的相转移催化剂，用于合成3-乙酰基吲哚3(a-e)的N-烷基衍生物5(a-t)，产率优异。2(a-e)本身是通过吲哚1(a-e)与氰基乙酸在丙酸酐存在下于100°C反应5-10分钟得到的。在热酸性条件下部分水解2(a-e)，得到相应的羧酰胺α-(3-吲哚羧酰基)乙酰胺4(a-e)，这些羧酰胺可以通过与5%氢氧化钠水溶液回流2-2.5小时，容易地转化为相应的3(a-e)。

  DOI：

  10.2174/157017811799304395
• 作为产物：
  描述：

  5-硝基吲哚 、 氰乙酸 在 丙酸酐 作用下， 生成 3-(5-nitro-1H-indol-3-yl)-3-oxopropanenitrile
  参考文献：
  名称：

  Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst

  摘要：

  报道了一种利用5%氢氧化钠水溶液，将3-氰基乙酰基吲哚2(a-e)高效转化为3-乙酰基吲哚3(a-e)的简便方法。四丁基溴化铵（TBAB）被发现是一种有效的相转移催化剂，用于合成3-乙酰基吲哚3(a-e)的N-烷基衍生物5(a-t)，产率优异。2(a-e)本身是通过吲哚1(a-e)与氰基乙酸在丙酸酐存在下于100°C反应5-10分钟得到的。在热酸性条件下部分水解2(a-e)，得到相应的羧酰胺α-(3-吲哚羧酰基)乙酰胺4(a-e)，这些羧酰胺可以通过与5%氢氧化钠水溶液回流2-2.5小时，容易地转化为相应的3(a-e)。

  DOI：

  10.2174/157017811799304395

文献信息

• Facile Synthesis of Substituted 3-(1-Ethyl-1H-indol-3-yl)-2-(1-methyl-1Hindole- 3-carbonyl)acrylonitrile and Their Antimicrobial Activities
  作者：G. Thirupathi、M. Venkatanarayana、P.K. Dubey、Y. Bharathi Kumari

  DOI：10.14233/ajchem.2013.15382

  日期：——

  Facile syntheses of substituted 3-(1-methyl-1H-indol-3-yl)-2-(1-ethyl-1H-indole-3-carbonyl)acrylonitriles 5(a-d) is being reported. L-Tyrosine has been utilized as an efficient and eco-friendly catalyst in water at room temperature for Knoevenagel condensation of N-ethyl indole-3-carboxyaldehyde (2) with 3-cyanoacetylindole contain active methylene group 3(a-d), at room temperature to afford substituted 3-(1-ethyl-1H-indol-3-yl)-2-(1H-indole-3- carbonyl)acrylonitrile 4(a-d), respectively. Subsequently these products were treated with dimethyl sulfate in the presence of Na2CO3 as a base and triethyl benzylammonium chloride (TEBAC) as phase transfer catalyst in DMF at room temperature for 1 h to afford the corresponding substituted 3-(1-ethyl-1H-indol-3-yl)-2-(1-methyl-1H-indole-3-carbonyl)acrylonitrile 5(a-d). The antibacterial and antifungal activities of 4(a-d) and 5(a-d) have been studied.

  报告了一种方便的合成取代的3-(1-甲基-1H-吲哚-3-基)-2-(1-乙基-1H-吲哚-3-羧基)酸腈5(a-d)的方法。采用L-酪氨酸作为高效且环保的催化剂，在室温下以水为环境，进行N-乙基吲哚-3-甲醛(2)与含活性亚甲基基团的3-氰基乙酰吲哚3(a-d)的克诺文纳尔缩合，最终得到取代的3-(1-乙基-1H-吲哚-3-基)-2-(1H-吲哚-3-羧基)酸腈4(a-d)。随后，这些产物在DMF中，以Na2CO3作为碱，三乙基苄铵氯化物(TEBAC)作为相转移催化剂，在室温下反应1小时，得到相应的取代3-(1-乙基-1H-吲哚-3-基)-2-(1-甲基-1H-吲哚-3-羧基)酸腈5(a-d)。研究了4(a-d)和5(a-d)的抗菌和抗真菌活性。
• <scp>l</scp>-Proline-Catalyzed Knoevenagel Condensation: A Tandem Synthesis of 3-Acetylcoumarinoindoles and Their<i>N</i>-Alkyl Derivatives by Using PEG-600 as the Reaction Medium
  作者：M. Venkatanarayana、P. K. Dubey

  DOI：10.1002/jhet.1784

  日期：2014.7

  A tandem synthesis of 3‐acetylcoumarinoindoles 5a, 5b, 5c, 5d, 5e in the presence of catalytic amount of l‐proline in ethanol medium is reported. l‐proline has been utilized as an efficient and eco‐friendly catalyst for the Knoevenagel condensation of 3‐cyanoacetylindoles 1a, 1b, 1c, 1d, 1e with 2‐hydroxybenzaldehyde (2) to afford the corresponding substituted 3‐(1H‐indol‐3‐yl)2‐(2‐hydroxybenzylid

  据报道，在乙醇培养基中催化量的l-脯氨酸存在下，串联合成3-乙酰香豆素吲哚5a，5b，5c，5d，5e。l脯氨酸已被用作高效，环保的催化剂，用于3-氰基乙酰吲哚1a，1b，1c，1d，1e与2-羟基苯甲醛（2）的Knoevenagel缩合反应，从而提供相应的取代的3-（1 H-吲哚-3-基）2-（2-羟基亚苄基）-3-氧代丙烷腈3（a-e），未经隔离处理的则用热浓溶液处理。HCl可以高产率提供3-乙酰香豆素吲哚4a，4b，4c，4d，4e。随后，将它们与硫酸二甲酯在PEG-600（印度安得拉邦海得拉巴）作为高效绿色溶剂存在下反应，得到相应的N-甲基-3-乙酰香豆素吲哚5a，5b，5c，5d，5e。中等产量。
• Venkatanarayana; Dubey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 6, p. 810 - 813
  作者：Venkatanarayana、Dubey

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents
  作者：Pravin S. Bhale、Hemant V. Chavan、Rupali S. Endait、Ashok T. Kadam、Rajesh J. Bopalkar、Mandar S. Gaikwad

  DOI：10.5562/cca3758

  日期：——
• Facile and Green Syntheses of 2-(N-Methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles and a Study of Their Antimicrobial Activities
  作者：G. Thirupathi、M. Venkatanarayana、P. K. Dubey、Y. Bharathi Kumari

  DOI：10.1080/00397911.2012.744055

  日期：2013.11.17

  Facile and green syntheses of substituted-2-(N-methylindole-3-carbonyl)-3-(N-methyl pyrrol-2-yl) acrylonitriles 6a-d are being reported. L-Proline has been utilized as an efficient and ecofriendly catalyst in aqueous medium for Knoevenagel condensation of pyrrole-2-carboxyaldehyde (1) and its N-methyl derivative (2) with the active methylene compounds 3-cyanoacetylindoles 3a-d at room temperature to afford substituted-2-(1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitriles 4a-d and substituted-2-(1H-indole-3-carbonyl)-3-(N-methylpyrrol-2-yl) acrylonitriles 5a-d respectively. Subsequently these products were treated with dimethyl sulfate (DMS) in polythylene glycol (PEG)-600 as an efficient and green solvent to afford the corresponding substituted-2-(N-methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles 6a-d. The antibacterial and antifungal activities of 4a-d, 5a-d, and 6a-d have been studied. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]