Furan-2-yl-indol-1-yl-methanone | 74117-32-1

• 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: Furan-2-yl-indol-1-yl-methanone
• 英文别名: Furan-2-yl(indol-1-yl)methanone
• CAS: 74117-32-1
• 化学式: C₁₃H₉NO₂
• 分子量: 211.22
• InChiKey: BHKCEZYLFLMDBR-UHFFFAOYSA-N

物化性质

• 沸点：
  282.5±22.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Furan-2-yl-indol-1-yl-methanone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以99%的产率得到糠酸（呋喃甲酸）
  参考文献：
  名称：

  2-(2-Aminophenyl)-acetaldehyde Dimethyl Acetal: A Novel Reagent for the Protection of Carboxylic Acids.

  摘要：

  The synthesis and use of 2-(2-aminophenyl)-acetaldehyde dimethyl acetal 1 are described. The amides 2, derived from this amine and carboxylic acids, are stable under basic conditions and thus can be regarded as the protected carboxylic acids. The corresponding carboxylic acids are regenerated by conversion of 2 into indolylamides 3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition, 3 can be easily converted to esters, amides, and aldehydes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10491-9
• 作为产物：
  描述：

  2-(2,2-二甲氧基乙基)苯甲酰胺 在 吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 Furan-2-yl-indol-1-yl-methanone
  参考文献：
  名称：

  2-(2-Aminophenyl)-acetaldehyde Dimethyl Acetal: A Novel Reagent for the Protection of Carboxylic Acids.

  摘要：

  The synthesis and use of 2-(2-aminophenyl)-acetaldehyde dimethyl acetal 1 are described. The amides 2, derived from this amine and carboxylic acids, are stable under basic conditions and thus can be regarded as the protected carboxylic acids. The corresponding carboxylic acids are regenerated by conversion of 2 into indolylamides 3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition, 3 can be easily converted to esters, amides, and aldehydes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10491-9

文献信息

• Scaffold hopping by net photochemical carbon deletion of azaarenes
  作者：Jisoo Woo、Alec H. Christian、Samantha A. Burgess、Yuan Jiang、Umar Faruk Mansoor、Mark D. Levin

  DOI：10.1126/science.abo4282

  日期：2022.4.29

  Discovery chemists routinely identify purpose-tailored molecules through an iterative structural optimization approach, but the preparation of each successive candidate in a compound series can rarely be conducted in a manner matching their thought process. This is because many of the necessary chemical transformations required to modify compound cores in a straightforward fashion are not applicable

  发现化学家通常通过迭代结构优化方法来识别特定目的的分子，但化合物系列中每个连续候选分子的制备很少能够以与其思维过程相匹配的方式进行。这是因为以简单的方式修改化合物核心所需的许多必要的化学转化并不适用于复杂的环境。我们报告了一种方法，通过允许化学家直接在化学上不同的杂芳族支架之间跳跃来解决这个问题的一个方面。具体来说，我们表明用 390 纳米光选择性光解喹啉 N-氧化物，然后进行酸促进重排，得到 N-酰基吲哚，同时显示出与医学相关功能的广泛相容性。演示了对具有药学意义的化合物的后期骨架修饰以及涉及连续单原子变化的更复杂转化的应用。
• Visible‐Light‐Enabled Multicomponent Cascade Transformation from Indoles to 2‐Azidoindolin‐3‐yl 2‐Aminobenzoates
  作者：Ling‐Ling Zhang、Meng‐Meng Xu、Wen‐Bin Cao、Xiao‐Ping Xu、Shun‐Jun Ji

  DOI：10.1002/adsc.202000637

  日期：2020.8.4

  The synthesis of 2‐azido‐1‐benzoylindolin‐3‐yl 2‐benzamidobenzoate commencing from (1H‐indol‐1‐yl)(phenyl)methanone and trimethylsilyl azide (TMSN3) under oxygen atmosphere is described in this paper. This transformation proceeds via a sequential dearomatization and ring‐opening cascade reaction of indoles in a cascade manner.

  本文描述了在氧气气氛下由（1 H-吲哚-1-基）（苯基）甲酮和三甲基甲硅烷基叠氮化物（TMSN 3）合成2-叠氮基-1-苯甲酰基吲哚-3-基-2-苯甲酰胺基苯甲酸。这种转化通过级联方式依次进行吲哚的脱芳香化和开环级联反应进行。
• DMAPO/Boc ₂ O‐Mediated One‐Pot Direct <i>N</i> ‐Acylation of Less Nucleophilic <i>N</i> ‐Heterocycles with Carboxylic Acids
  作者：Atsushi Umehara、Soma Shimizu、Makoto Sasaki

  DOI：10.1002/cctc.202201596

  日期：2023.3.8

  Nitrogen Nucleophiles: A general method for direct N-acylation of less nucleophilic nitrogen heterocycles with carboxylic acids is reported. The method, which uses simple, commercially available reagents, no metals and user-friendly conditions, shows excellent functional group tolerance and broad substrate scope for both nitrogen nucleophiles and carboxylic acids.

  氮亲核试剂：报道了用羧酸对亲核性较低的氮杂环进行直接N-酰化的一般方法。该方法使用简单、市售的试剂、无金属和用户友好的条件，对含氮亲核试剂和羧酸显示出优异的官能团耐受性和广泛的底物范围。
• Dearomatization of Indoles via Azido Radical Addition and Dioxygen Trapping To Access 2-Azidoindolin-3-ols
  作者：Meng-Meng Xu、Wen-Bin Cao、Rao Ding、Hai-Yan Li、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1021/acs.orglett.9b02009

  日期：2019.8.16

  Efficient copper-catalyzed aerobic oxidative dearomatization of indoles with trimethylsilyl azide (TMSN3) for the synthesis of 2-azidoindolin-3-ols has been developed. Molecular oxygen served as the oxygen-atom source in this transformation. The multicomponent reaction is appreciated by its high site- and diastereoselectivity, broad substrate scope, and mild conditions at room temperature.