5,5'-dimethoxyisoindigo | 1237738-67-8

• 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: 5,5'-dimethoxyisoindigo
• 英文别名: 55DMIId；5-methoxy-3-(5-methoxy-2-oxo-1H-indol-3-ylidene)-1H-indol-2-one
• CAS: 1237738-67-8
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: FRZJZKSCYSYBKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 5,5'-dimethoxyisoindigo 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Redox-tunable isoindigos for electrochemically mediated carbon capture

  摘要：

  Efficient CO2 separation technologies are essential for mitigating climate change. Compared to traditional thermochemical methods, electrochemically mediated carbon capture using redox-tunable sorbents emerges as a promising alternative due to its versatility and energy efficiency. However, the undesirable linear free-energy relationship between redox potential and CO2 binding affinity in existing chemistry makes it fundamentally challenging to optimise key sorbent properties independently via chemical modifications. Here, we demonstrate a design paradigm for electrochemically mediated carbon capture sorbents, which breaks the undesirable scaling relationship by leveraging intramolecular hydrogen bonding in isoindigo derivatives. The redox potentials of isoindigos can be anodically shifted by >350 mV to impart sorbents with high oxygen stability without compromising CO2 binding, culminating in a system with minimised parasitic reactions. With the synthetic space presented, our effort provides a generalisable strategy to finetune interactions between redox-active organic molecules and CO2, addressing a longstanding challenge in developing effective carbon capture methods driven by non-conventional stimuli.

  DOI：

  10.1038/s41467-024-45410-z
• 作为产物：
  描述：

  5-甲氧基吲哚酮 在 iron(II) chloride 作用下， 以 戊醇 为溶剂， 以89 %的产率得到5,5'-dimethoxyisoindigo
  参考文献：
  名称：

  铁催化通过吲哚啉-2-酮的氧化C(sp3)-H功能化选择性构建吲哚衍生物

  摘要：

  考虑到开发强大的催化剂的重要性和吲哚衍生物的药效团特征，我们描述了一种铁催化的吲哚啉-2-酮氧化C(sp 3 )–H功能化的可转换方法。使用FeCl 2作为催化剂、空气作为氧化剂、醇作为溶剂，选择性转化表现出优异的活性和化学选择性。通过控制反应条件，特别是溶剂的选择、催化剂负载量和反应顺序，选择性地合成了一系列有价值的吲哚衍生物，包括靛红以及对称和非对称异靛，收率良好至优异。此外，在简单条件下克级合成具有生物抗癌活性的化合物凸显了其在实际应用中的巨大潜力。

  DOI：

  10.1039/d4ob00133h

文献信息

• One step synthesis of indirubins by reductive coupling of isatins with KBH 4
  作者：Cuiling Wang、Jiaxu Yan、Mo Du、Joseph A. Burlison、Chi Li、Yanni Sun、Danqing Zhao、Jianli Liu

  DOI：10.1016/j.tet.2017.03.077

  日期：2017.5

  One step synthesis of the natural product indirubin by reductive coupling of isatin with KBH4 is described and a possible mechanism for the reaction is proposed. Eleven indirubin derivatives were obtained easily from the corresponding substituted isatin.

  描述了通过Isatin与KBH 4的还原偶联一步一步合成天然产物靛玉红的方法，并提出了可能的反应机理。从相应的取代的靛红很容易获得11种靛玉红衍生物。
• 一种有机催化靛红自缩合制备异靛蓝类化合 物的方法
  申请人：大连理工大学

  公开号：CN111233741B

  公开（公告）日：2021-04-16

  本发明公开了一种有机催化靛红自缩合制备异靛蓝类化合物的方法，涉及有机合成、染料、医药化工及有机光电材料等技术领域。该方法以靛红及其衍生物为原料，有机胺作为催化剂，通入羰基硫，在25～100摄氏度条件下搅拌8～24小时制备功能化异靛蓝类化合物。该反应具有反应条件温和、操作简单、官能团耐受性好、转化率高、产率高、化学选择性好等特点，在染料、有机光电材料、天然产物合成、医药化工等领域中具有潜在的应用前景。
• <scp>π‐Extension</scp> of Isoindigos (<scp>IIDs</scp>) through C—H/N—H Activation and Alkyne Annulation^†
  作者：Kang Wang、Liangliang Chen、Yan‐Ying Huang、Liyuan Qin、Cheng Li、Xi‐Sha Zhang、Feixian Luo、Zheng Duan、Guanxin Zhang、Deqing Zhang

  DOI：10.1002/cjoc.202300149

  日期：2023.10.15

  dye and conjugated unit in opto-electronic materials. Functionalization of IID to increase its structural complexity is demanding for obtaining diversity properties. Herein, we developed a direct C—H/N—H activation method of IIDs via double alkyne annulations and synthesized π-extended IIDs with two pairs of 5/7 membered rings. The structure of the π-extended IIDs was characterized and confirmed by

  异靛蓝（IID）作为有机染料和共轭单元广泛应用于光电材料中。为了获得多样性特性，需要对 IID 进行功能化以增加其结构复杂性。在此，我们开发了一种通过双炔环直接 C—H/N—H 激活 IID 的方法，并合成了具有两对 5/7 元环的 π 扩展 IID。通过1 H NMR、13 C NMR、HRMS 和 X 射线晶体分析对 π 扩展 IID 的结构进行了表征和确认。通过紫外-可见吸收、循环伏安法和热重分析对其物理性质进行了表征。与非环形类似物相比，环形产品的吸收系数显着增强。
• Substituted <i>E</i>-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells
  作者：Aldo Andreani、Stefania Bellini、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Maddalena Zini、Claudio Stefanelli、Lanfranco Masotti、Robert H. Shoemaker

  DOI：10.1021/jm1007165

  日期：2010.8.12

  The synthesis of new substituted E-3-(3-indolylmethylene)-1,3-dihydroindo1-2-ones is reported. The antitumor activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. Structure activity relationships are discussed. The action of selected compounds was investigated in MCF-7 breast cancer cells. The ability of these derivatives to inhibit cellular proliferation was accompanied by increased level of p53 and its transcriptional targets p21 and Bax, interference in the cell cycle progression with cell accumulation in the G2/M phase, and activation of apoptosis.