(E)-5-methoxy-3-(phenylimino)indolin-2-one | 1578230-01-9

• 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: (E)-5-methoxy-3-(phenylimino)indolin-2-one
• CAS: 1578230-01-9；1578230-74-6；861335-91-3
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: ZLLIJUIYHQDIGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-甲氧基靛红 、 苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以77.778%的产率得到
  参考文献：
  名称：

  金催化炔烯酮与亚氨基吲哚的级联反应，得到 3,2'-吡咯烷基-螺吲哚衍生物

  摘要：

  在此，通过级联环异构化/(3 + 2)环化过程开发了金催化的炔烯酮与亚氨基氧吲哚的级联反应。该方法为合成功能化 3,2'-吡咯烷基-螺吲哚提供了一种简单有效的途径，具有高反应活性、广泛的底物范围和优异的顺式选择性。此外，呋喃单元的后续官能化允许螺吲哚衍生物的多样化合成，这些衍生物已表现出良好的抗肿瘤活性。

  DOI：

  10.1021/acs.orglett.4c01395

文献信息

• Protecting-Group-Free Synthesis of 3-Amino-3-α-prenyl-oxindoles through the Direct Prenylation of Isatin-Derived Imines
  作者：De-Feng Li、Hai-Shan Jin、Jing-Ru Zhang、Yi-Xuan Jiang、Li-Ming Zhao

  DOI：10.1002/ejoc.201800881

  日期：2018.9.16

  A zinc‐mediated α‐selective prenylation of isatin‐derived imine in a sealed tube has been developed. The method is highly efficient and operationally simple with its use of readily available prenyl bromide as the prenyl source. The obtained prenylated adduct can be further manipulated to other more complicated derivatives through cyclization or oxidation.

  已开发出在密封管中由锌介导的α-伊斯丁衍生的亚胺选择性乙二烯基化。该方法通过使用容易获得的异戊烯基溴化物作为异戊二烯源来进行高效和操作简单。可以通过环化或氧化将所得的烯丙基化的加合物进一步操纵为其他更复杂的衍生物。
• One-Pot Solvent Free, Green Route to Novel Substituted Spiro[oxindole-isoxazolidine] Derivatives: Novel Candidates as Antimicrobial Agents
  作者：Manpreet Kaur、Sumeet Kaur Bhatia、Baldev Singh

  DOI：10.14233/ajchem.2021.23164

  日期：——

  solvent-free synthesis of ketonitrones may not always be accomplished by simple condensation reactions. The occasional reports of green synthetic routes toward these compounds have been reported. The key features of this 1,3-dipolar cycloaddition reactions of N-[4-(-carboxycyclohexylmethyl)]maleimide with substituted isatin ketonitrone under microwave conditions resulted in the green synthesis of series

  环境友好的催化剂和酮硝酮的无溶剂合成并不总是通过简单的缩合反应来完成。偶尔有关于这些化合物的绿色合成路线的报道。N-[4-(-羧基环己基甲基)]马来酰亚胺与取代靛红酮硝酮在微波条件下进行1,3-偶极环加成反应的关键特征导致一系列新型氟取代螺[羟吲哚-异恶唑烷]衍生物的绿色合成产率高，纯度提高，反应时间短。所有合成的化合物均已被鉴定为有效的体外抗菌剂。这些结果促进了以生态友好的方式合成具有巨大药理学重要性的螺[羟吲哚-异恶唑烷]衍生物的绿色路线。
• Highly diastereoselective synthesis of imidazolidine-dispirooxindoles via three-component [3 + 2] cycloadditions of isatins, 2-(aminomethyl)pyridine and isatin-based imines
  作者：Hong-Wu Zhao、Xiao-Qin Chen、Zhao Yang、Ting Tian、Bo Li、Wei Meng、Xiu-Qing Song、Hai-Liang Pang

  DOI：10.1039/c5ra21995g

  日期：——

  isatins, 2-(aminomethyl)pyridine and isatin-based imines proceeded readily, and furnished novel imidazolidine-dispirooxindoles in up to 84% yield with up to >99 : 1 diastereoselectivity. The relative configuration of the imidazolidine-dispirooxindoles was firmly confirmed on the basis of X-ray single crystal structure analysis. The reaction mechanism was assumed to account for the diastereoselective formation

  在存在Et 3 N的情况下，靛红，2-（氨基甲基）吡啶和基于靛红的亚胺的[3 + 2]环加成反应很容易进行，并以高达84％的产率提供了新颖的咪唑烷-二螺环辛多烯，其产率高达> 99： 1非对映选择性。基于X射线单晶结构分析，牢固地确认了咪唑烷-二螺并氧辛酯的相对构型。假定该反应机理解释了咪唑烷-二螺并恶唑的非对映选择性形成。
• Lewis acid-catalyzed [4 + 2] cycloaddition of donor–acceptor cyclobutanes with iminooxindoles: access to spiro[piperidine-3,2′-oxindoles]
  作者：Zuliang Chen、Keyi Yan、Hui Luo、Jun Yan、Yang Zeng

  DOI：10.1039/d2ra04730f

  日期：——

  approach is described for the synthesis of spiro[piperidine-3,2'-oxindoles] in 35-82 yields with excellent stereoselectivity via the [4 + 2] cycloaddition reaction of donor-acceptor cyclobutanes with iminooxindoles in the presence of 10-30 mol% Sc(OTf)3 at room temperature. This methodology provides great potential for building spiro-heterocycle compounds from simple building blocks.

  描述了一种合成螺 [piperidine-3,2'-oxindoles] 的新方法，产率为 35-82，通过供体-受体环丁烷与 iminooxindoles 在 10-室温下 30 mol% Sc(OTf)3。这种方法为从简单的构建块构建螺杂环化合物提供了巨大的潜力。
• Remote Activation of the Nucleophilicity of Isatin
  作者：Sergei Žari、Marina Kudrjashova、Tõnis Pehk、Margus Lopp、Tõnis Kanger

  DOI：10.1021/ol500421k

  日期：2014.3.21

  The concept of the remote activation of reactivity was first applied in asymmetric organocatalysis. An isatin 3-phenylimine derivative acts as a donor in the thiourea catalyzed asymmetric addition to unsaturated 1,4-ketoesters, affording aza-Michael adducts in high enantiomeric purity and yield.