5-methoxy-indoline-2,3-dione-3-phenylhydrazone

• 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: 5-methoxy-indoline-2,3-dione-3-phenylhydrazone
• 英文别名: 5-Methoxy-indolin-2,3-dion-3-phenylhydrazon；5-methoxy-3-(2-phenylhydrazinyl)indol-2-one
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: OYGMDZBRPHFLAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-methoxy-indoline-2,3-dione-3-phenylhydrazone 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以71%的产率得到(3Z)-5-hydroxy-1H-indole-2,3-dione 3-(phenylhydrazone)
  参考文献：
  名称：

  Synthesis and biophysical evaluation of arylhydrazono-1H-2-indolinones as β-amyloid aggregation inhibitors

  摘要：

  A series of isatin-3-arylhydrazones were synthesized and evaluated in vitro as inhibitors of A beta(1-40) aggregation using a thioflavin T fluorescence method. An exploration of the effects on A beta(1-40) aggregation of a number of diverse substituents at phenylhydrazone group and 5,6- positions of the indolinone nucleus led us to single out some new anti-aggregating compounds with IC50 values in the low micromolar range. The most active compounds carry methoxy- or hydroxy- substituents in the indolinone 5,6-positions and lipophilic groups such as iPr and Cl at 4'- and 3'-position, respectively, of the phenylhydrazone moiety. Two derivatives are noteworthy, namely 18 (IC50 = 0.4 mu M) and 42 (IC50 = 1.1 mu M). The in vitro effects of the highly active, water soluble, compound 42 on the temporal evolution of A beta(1-40) fibrils formation were further investigated by circular dichroism spectroscopy, transmission electron microscopy and dynamic light scattering studies, which clearly showed that this compound delayed and lowered the amyloid fibril formation. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.015
• 作为产物：
  描述：

  苯肼 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5-methoxy-indoline-2,3-dione-3-phenylhydrazone
  参考文献：
  名称：

  Halberkann, Chemische Berichte, 1921, vol. 54, p. 3096

  摘要：

  DOI：

文献信息

• Simple and efficient approach for synthesis of hydrazones from carbonyl compounds and hydrazides catalyzed by meglumine
  作者：Mo Zhang、Ze-Ren Shang、Xiao-Tang Li、Jia-Nan Zhang、Yong Wang、Kang Li、Yang-Yang Li、Zhan-Hui Zhang

  DOI：10.1080/00397911.2016.1258476

  日期：2017.1.17

  ABSTRACT A simple, environmentally benign protocol for synthesis of hydrazones from carbonyl compounds and hydrazides has been developed in the presence of meglumine in aqueous-ethanol media at room temperature. The salient features of the present protocol are mild reaction conditions, short reaction time, high yields, operational simplicity, metal-free, applicability toward large-scale synthesis, and biodegradable

  摘要 在葡甲胺存在的情况下，在室温下，在乙醇水溶液中，已经开发出一种简单、环境友好的方案，用于从羰基化合物和酰肼合成腙。本协议的显着特点是反应条件温和、反应时间短、产量高、操作简单、不含金属、适用于大规模合成以及可生物降解且价格低廉的催化剂。图形概要
• Indium(<scp>iii</scp>)-catalyzed efficient synthesis of 3-arylhydrazonoindolin-2-ones and their fluorescent metal sensing studies
  作者：Shreedhar Devkota、Sonaimuthu Mohandoss、Yong Rok Lee

  DOI：10.1039/d1nj05715d

  日期：——

  In(iii)-catalyzed strategy for the preparation of 3-arylhydrazonoindolin-2-ones from 3-diazoindoles is developed and used for Fe³⁺ and Hg²⁺ ion sensing.

  研发了一种以In(iii)为催化剂的策略，用于从3-重氮吲哚制备3-芳基肼基吲哚啉-2-酮，并用于Fe3+和Hg2+离子传感。
• Visible-light-absorbing C–N cross-coupling for the synthesis of hydrazones involving C(sp²)–H/C(sp³)–H functionalization
  作者：Ambuj Kumar Kushwaha、Suresh Kumar Maury、Arsala Kamal、Himanshu Kumar Singh、Shikha Pandey、Sundaram Singh

  DOI：10.1039/d2cc07001d

  日期：——

  An efficient C–N cross-coupling approach for the synthesis of hydrazones was developed through C(sp2)–H and C(sp3)–H functionalization of indole and methylarene under visible light irradiation using photocatalyst eosin Y, ethanol:water as a green solvent and atmospheric air as an oxidant. With the aid of eosin Y, the C–H bonds of indole and methylarenes were activated followed by coupling with arylhydrazines

  通过 C(sp 2 )–H 和 C(sp 3)–H 功能化吲哚和甲基芳烃在可见光照射下使用光催化剂曙红 Y，乙醇：水作为绿色溶剂和大气空气作为氧化剂。在曙红 Y 的帮助下，吲哚和甲基芳烃的 C-H 键被激活，然后与芳基肼偶联。该程序适用于具有良好官能团相容性的各种底物，提供了一种创造性的方法，可以用廉价且易于获得的原材料制造腙。没有金属、低成本、环境友好、绿色溶剂、无毒、易于处理以及利用可见光等可再生能源是该方法的一些主要优势。
• 10.1002/ejoc.202400439
  作者：Soam, Pooja、Mandal, Debasish、Tyagi, Vikas

  DOI：10.1002/ejoc.202400439

  日期：——

  method for accessing indole-based N-carboxamide derivatives by palladium-catalyzed isocyanide insertion into the N−H bond of 3-(phenylhydrazono)oxindole is developed. Further, control experiments and Conceptual DFT calculation suggest that the 3-phenylhydrazone group plays a crucial role in remotely activating the N−H bond of oxindole derivatives. In addition, it has been observed that the reaction‘s outcome

  开发了一种通过钯催化的异氰化物插入 3-(苯基亚肼基)羟吲哚的 NH 键来获得基于吲哚的 N-甲酰胺衍生物的便捷方法。此外，控制实验和概念DFT计算表明，3-苯基腙基团在远程激活羟吲哚衍生物的NH键中起着至关重要的作用。此外，据观察，反应的结果高度依赖于取代基的电子效应。
• Bauer, Chemische Berichte, 1909, vol. 42, p. 2110
  作者：Bauer

  DOI：——

  日期：——