5-acetyl-1-methylindoline-2,3-dione

• 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: 5-acetyl-1-methylindoline-2,3-dione
• 英文别名: 1H-Indole-2,3-dione, 5-acetyl-1-methyl-；5-acetyl-1-methylindole-2,3-dione
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: CAHYOYDJQOYIKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 氧气 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以50%的产率得到5-acetyl-1-methylindoline-2,3-dione
  参考文献：
  名称：

  Copper-Catalyzed Intramolecular C−H Oxidation/Acylation of Formyl-N-arylformamides Leading to Indoline-2,3-diones

  摘要：

  A new, efficient Cu-catalyzed intramolecular C-H oxidation/acylation method has been developed for the synthesis of substituted indoline-2,3-diones (isatins). In the presence of CuCl, and O-2, a variety of formyl-N-arylformamides underwent the tandem reaction to afford the corresponding indoline-2,3-diones in moderate to good yields. It is noteworthy that the reaction serves as the first example of transition-metal-catalyzed transformation for the preparation of indoline-2,3-diones.

  DOI：

  10.1021/ja103426d

文献信息

• Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization
  作者：Ming-Bo Zhou、Yang Li、Xuan-Hui Ouyang、Jin-Heng Li

  DOI：10.1007/s11426-019-9633-x

  日期：2020.2

  A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H

  描述了通过C tripleC三键裂解和C（sp 2）-H官能化作用，将新的钯催化的N-芳基丙酰胺和H 2 O氧化转化为各种二氢吲哚-2,3-二酮和酸的过程，这一点受到促进。催化的CuBr的协作动作2，2,2,6,6-四甲基-1-哌啶氧（TEMPO）和O 2。该方法通过C–H官能化策略为炔烃的转化提供了实用的工具，该方法可在单个反应中形成一个C–C键和多个C–O键，并具有高的底物相容性和出色的官能团耐受性。
• Design, Synthesis, and Evaluation of Nonpeptidic Inhibitors of Human Rhinovirus 3C Protease
  作者：Stephen E. Webber、Jayashree Tikhe、Stephen T. Worland、Shella A. Fuhrman、Thomas F. Hendrickson、David A. Matthews、Robert A. Love、Amy K. Patick、James W. Meador、Rose Ann Ferre、Edward L. Brown、Dorothy M. DeLisle、Clifford E. Ford、Susan L. Binford

  DOI：10.1021/jm960603e

  日期：1996.1.1

  The design, synthesis, and biological evaluation of reversible, nonpeptidic inhibitors of human rhinovirus (HRV) 3C protease (3CP) are reported. A novel series of 2,3-dioxindoles (isatins) were designed that utilized a combination of protein structure-based drug design, molecular modeling, and structure-activity relationship (SAR). The C-2 carbonyl of isatin was envisioned to react in the active site

  报告了人类鼻病毒（HRV）3C蛋白酶（3CP）可逆的非肽类抑制剂的设计，合成和生物学评估。设计了一系列新颖的2,3-二恶英（isatins），它结合了基于蛋白质结构的药物设计，分子建模和结构-活性关系（SAR）。可以想象，靛红的C-2羰基会在HRV 3CP的活性位点与负责催化蛋白水解的半胱氨酸反应，从而形成稳定的过渡态模拟物。使用人类鼻病毒血清型14（HRV-14）3CP的载脂蛋白晶体结构和肽底物模型进行分子建模实验，使我们能够分别从P5和1位的P1和P2亚位点设计识别特征。 Isatin。尝试在5位使用SAR优化P1子位点的识别特性。另外，对几种5-取代的靛红进行了一系列从头算的计算，以研究硫化物加合物在C-3处的稳定性。抑制剂是通过一般的合成方法制备的，几乎在每种情况下都从可商购的5取代的isatins开始。测试所有化合物对纯化的HRV-14 3CP的抑制作用。与其他蛋白水解酶（包括胰
• Oxidative Radical Cyclization of <i>N</i> -methyl-<i>N</i> -arylpropiolamide to Isatins via Cleavage of the Carbon-carbon Triple Bond
  作者：Yan-Yan Liao、Yong-Chao Gao、Wenxu Zheng、Ri-Yuan Tang

  DOI：10.1002/adsc.201800592

  日期：2018.9.3

  A radical cyclization of N‐methyl‐N‐arylpropiolamide to isatins via an oxidative cleavage of a carbon‐carbon triple bond has been developed. In the presence of oxone and NaNO2, a variety of N‐methyl‐N‐arylpropiolamides were smoothly transformed into isatins. A nitration reaction proceeded along with the oxidative cyclization; both nitrated and non‐nitrated isatins were obtained in a one‐pot reaction

  已开发出通过碳-碳三键的氧化裂解将N-甲基-N-芳基丙醇酰胺自由基环化为靛红的方法。在存在丙酮和NaNO 2的情况下，各种N-甲基-N-芳基丙酰胺都可以平稳地转化为靛红。硝化反应与氧化环化一起进行。一锅反应可同时获得硝化和未硝化的靛红，总收率中等至良好。这是通过碳-碳三键的氧化自由基裂解合成Isatin的第一个例子。
• Copper-Catalyzed Intramolecular C−H Oxidation/Acylation of Formyl-<i>N</i>-arylformamides Leading to Indoline-2,3-diones
  作者：Bo-Xiao Tang、Ren-Jie Song、Cui-Yan Wu、Yu Liu、Ming-Bo Zhou、Wen-Ting Wei、Guo-Bo Deng、Du-Lin Yin、Jin-Heng Li

  DOI：10.1021/ja103426d

  日期：2010.7.7

  A new, efficient Cu-catalyzed intramolecular C-H oxidation/acylation method has been developed for the synthesis of substituted indoline-2,3-diones (isatins). In the presence of CuCl, and O-2, a variety of formyl-N-arylformamides underwent the tandem reaction to afford the corresponding indoline-2,3-diones in moderate to good yields. It is noteworthy that the reaction serves as the first example of transition-metal-catalyzed transformation for the preparation of indoline-2,3-diones.