methyl 2-(1H-indol-3-yl)-3-oxoindoline-2-carboxylate | 1305155-30-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(1H-indol-3-yl)-3-oxoindoline-2-carboxylate
• 英文别名: methyl 2-(1H-indol-3-yl)-3-oxo-1H-indole-2-carboxylate
• CAS: 1305155-30-9
• 化学式: C₁₈H₁₄N₂O₃
• 分子量: 306.321
• InChiKey: IBJDKNLIDMTGRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二甲基苯基甘氨酸-o-羧酸酯 在 ammonium cerium (IV) nitrate 、 potassium tert-butylate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 methyl 2-(1H-indol-3-yl)-3-oxoindoline-2-carboxylate
  参考文献：
  名称：

  Oxidative Coupling of Indoles with 3-Oxindoles

  摘要：

  A mild procedure for the union of 3-oxindoles with indoles is reported using oxidative coupling.

  DOI：

  10.3987/com-10-s(e)127

文献信息

• Oxidative Coupling of 3‐Oxindoles with Indoles and Arenes
  作者：Houng Kang、Adriana L. Jemison、Erin Nigro、Marisa C. Kozlowski

  DOI：10.1002/cssc.201900438

  日期：2019.7.5

  A highly efficient method for the oxidative coupling of 2‐substituted 3‐oxindoles with aromatic compounds to form 2,2‐disubstituted indolin‐3‐ones with broad scope is described. This work utilized oxygen as the terminal oxidant and a base‐metal catalyst under mild conditions instead of toxic/precious‐metal reagents and higher‐molecular‐weight oxidants. Quaternary structures were produced in modest‐to‐excellent

  描述了一种高效的方法，用于2-取代的3-氧吲哚与芳族化合物的氧化偶联，形成具有广泛应用范围的2,2-二取代的吲哚-3-酮。这项工作在温和的条件下利用氧气作为末端氧化剂和贱金属催化剂，而不是使用有毒/贵金属试剂和更高分子量的氧化剂。无需预功能化，即可以中等至出色的产率（高达96％）生产四级结构。
• [EN] TREATMENT OF INFECTIOUS DISEASE<br/>[FR] TRAITEMENT D'UNE MALADIE INFECTIEUSE
  申请人：UNIV ALBERTA

  公开号：WO2019183729A1

  公开（公告）日：2019-10-03

  The present disclosure relates to 2-(3 -indolyl)indolin-3 -one derivatives of the natural product isatisine A, synthesized from dual catalytic synthesis on metalocarbene-azide cascade chemistry, useful for treating a subject having or suspected of having an infectious disease, wherein said infectious disease is caused by a virus, wherein the virus is from the family flaviviridae or paramyxoviridae.

  本公开涉及从自然产物异黄酮A的2-(3-吲哚基)吲哚烷-3-酮衍生物中合成的双催化合成金属卡宾-叠氮化合物级联化学，用于治疗患有或疑似患有传染病的受试者，其中所述传染病由病毒引起，该病毒来自黄病毒科或副黏病毒科。
• Dual Catalytic Synthesis of Antiviral Compounds Based on Metallocarbene–Azide Cascade Chemistry
  作者：Bren Jordan P. Atienza、Lionel D. Jensen、Sarah L. Noton、Anil Kumar Victoria Ansalem、Tom Hobman、Rachel Fearns、David J. Marchant、F. G. West

  DOI：10.1021/acs.joc.8b00222

  日期：2018.7.6

  Aryl azides trap ortho-metallocarbene intermediates to generate indolenones possessing a reactive C-acylimine moiety, which can react with added indole nucleophiles to afford the 2-(3-indolyl)indolin-3-one scaffold found in the antiviral natural product isatisine A. This overall process occurs through a dual catalytic sequence at room temperature. Redox activation of the Cu(OTf)(2) precatalyst by indole results in catalytically competent Cu(I) required for azide-metal-locarbene coupling. The Bronsted acid that is also formed from Cu(OTf)(2) reduction is responsible for catalysis of the C-C bond-forming indole addition step. This modular, procedurally simple method allows for rapid assembly of bis(indole) libraries, several of which proved to have anti-infective activity against respiratory syncytial virus and Zika virus.
• TREATMENT OF INFECTIOUS DISEASE
  申请人：The Governors of the University of Alberta

  公开号：US20210009563A1

  公开（公告）日：2021-01-14

  The present disclosure relates to 2-(3-indolyl)indolin-3-one derivatives of the natural product isatisine A, synthesized from dual catalytic synthesis on metalocarbene-azide cascade chemistry, useful for treating a subject having or suspected of having an infectious disease, wherein said infectious disease is caused by a virus, wherein the virus is from the family flaviviridae or paramyxoviridae.