5,5′-difluoro-2-(5-fluoro-1H-indol-3-yl)-2,3′-biindolin-3-one | 1414941-76-6

• 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′-difluoro-2-(5-fluoro-1H-indol-3-yl)-2,3′-biindolin-3-one
• 英文别名: 5,5',5''-trifluoro-1H,1''H-[3,2':2',3''-terindol]-3'(1'H)-one；5-fluoro-2,2-bis(5-fluoro-1H-indol-3-yl)-1H-indol-3-one
• CAS: 1414941-76-6
• 化学式: C₂₄H₁₄F₃N₃O
• 分子量: 417.39
• InChiKey: ICJGTFQUHSLLFF-UHFFFAOYSA-N

物化性质

• 沸点：
  680.3±55.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氟吲哚 在 oxone 作用下， 以 水 为溶剂， 反应 9.0h， 以79%的产率得到5,5′-difluoro-2-(5-fluoro-1H-indol-3-yl)-2,3′-biindolin-3-one
  参考文献：
  名称：

  Nano Au/Pd-catalysed ‘on-water’ synthesis of C3–C3′ diaryl-oxindole scaffolds via N₂-selective dearomatization of indole

  摘要：

  使用微波“在水上”合成了Pd-rGO和Au–Pd-rGO纳米复合催化剂。这些催化剂被应用于合成2,2-双(吲哚-3-基)吲哚-3-酮。相比之下，Au–Pd-rGO纳米复合催化剂表现出更好的活性。

  DOI：

  10.1039/c9gc02370d

文献信息

• Metal-free catalyzed oxidative trimerization of indoles by using TEMPO in air: a biomimetic approach to 2-(1H-indol-3-yl)-2,3′-biindolin-3-ones
  作者：Wen-Bing Qin、Qiong Chang、Yun-Hong Bao、Ning Wang、Zheng-Wang Chen、Liang-Xian Liu

  DOI：10.1039/c2ob26390d

  日期：——

  simple, convenient and efficient metal-free catalyzed oxidative trimeric reaction of indoles toward a variety of 2-(1H-indol-3-yl)-2,3′-biindolin-3-one derivatives in moderate to excellent yields has been developed. This transformation proceeds via a tandem oxidative homocoupling reaction by using TEMPO in air as an environmentally benign oxidant. This methodology provides an alternative approach for the

  一种简单，便捷，有效的中度至优异收率的吲哚对各种2-（1 H-吲哚-3-基）-2,3′-联吲哚-3-酮衍生物的无金属催化氧化三聚反应发达。通过在空气中使用TEMPO作为环境友好的氧化剂，通过串联氧化均偶联反应进行该转化。该方法为在吲哚的C3位置直接生成全碳四元中心提供了另一种方法。
• Metal-Free–Catalyzed Oxidative Trimerization of Indoles Using NaNO₂ to Construct Quaternary Carbon Centers: Synthesis of 2-(1<i>H</i>-Indol-3-yl)-2,3′-biindolin-3-ones
  作者：Jun Xue、Yunhong Bao、Wenbing Qin、Jiayi Zhu、Yubo Kong、Hongen Qu、Zhengwang Chen、Liangxian Liu

  DOI：10.1080/00397911.2014.891743

  日期：2014.8.3

  convenient, and efficient synthesis of 2-(1H-indol-3-yl)-2,3′-biindolin-3-one derivatives via a transition-metal-free-catalyzed oxidative trimeric reaction of indoles has been developed. This transformation may have occurred through a tandem oxidative homocoupling reaction by using NaNO2 in pyridine as oxidant. This methodology provides an alternative approach for the direct generation of all-carbon

  摘要 开发了一种通过无过渡金属催化的吲哚氧化三聚反应简单、方便、有效地合成 2-(1H-indol-3-yl)-2,3'-biindolin-3-one 衍生物的方法。 . 这种转变可能是通过在吡啶中使用 NaNO2 作为氧化剂，通过串联氧化均偶联反应发生的。该方法为在吲哚的 C2 位置直接生成全碳四元中心提供了另一种方法。图形概要
• Copper-catalyzed oxidative trimerization of indoles by using TEMPO to construct quaternary carbon centers: the synthesis of 2-(1<i>H</i>-indol-3-yl)-2,3′-biindolin-3-ones
  作者：Yu-Bo Kong、Jia-Yi Zhu、Zheng-Wang Chen、Liang-Xian Liu

  DOI：10.1139/cjc-2013-0435

  日期：2014.4

  A simple, convenient, and efficient synthesis of 2-(1H-indol-3-yl)-2,3′-biindolin-3-one derivatives has been developed by the oxidative trimeric reaction of indoles using the TEMPO/CuCl₂ catalyst system under ambient air. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C-2 position of indoles.

  通过在常温下使用TEMPO/CuCl2催化剂体系对吲哚进行氧化三聚反应，开发了一种简单、方便和高效的合成2-(1H-吲哚-3-基)-2,3′-双吲哚-3-酮衍生物的方法。该方法为在吲哚的C-2位置直接生成全碳季铵中心提供了一种替代途径。
• Indole trimers with antibacterial activity against Gram-positive organisms produced using combinatorial biocatalysis
  作者：Kevin McClay、Shahila Mehboob、Jerry Yu、Bernard D Santarsiero、Jiangping Deng、James L Cook、Hyunyoung Jeong、Michael E Johnson、Robert J Steffan

  DOI：10.1186/s13568-015-0125-4

  日期：2015.12

  The I100V isoform of toluene-4-monooxygenase was used to catalyze the oxidative polymerization of anthranil and various indoles under mildly acidic conditions, favoring the production of trimers. Compounds produced in sufficient yield were purified and tested for their ability to inhibit the growth of B. anthracis, E. faecalis, L. monocytogenes, S. aureus, and in some cases, F. tularensis. 15 of the compounds displayed promising antibacterial activity (MIC < 5 µg/ml) against one or more of the strains tested, with the best MIC values being <0.8 µg/ml. All of these compounds had good selectivity, showing minimal cytotoxicity towards HepG2 cells. The structure was solved for six of the compounds that could be crystallized, revealing that minimally two classes of indole based trimers were produced. One compound class produced was a group of substituted derivatives of the natural product 2,2-bis(3-indolyl) indoxyl. The other group of compounds identified was classified as tryptanthrin-like compounds, all having multi-ring pendant groups attached at position 11 of tryptanthrin. One compound of particular interest, SAB-J85, had a structure that suggests that any compound, with a ring structure that can be activated by an oxygenase, might serve as a substrate for combinatorial biocatalysis.

  在弱酸性条件下，甲苯-4-单加氧酶的 I100V 异构体被用来催化蒽醌和各种吲哚的氧化聚合，从而有利于三聚体的生成。纯化并测试了以足够产量生产的化合物抑制炭疽杆菌、粪大肠杆菌、单核细胞增多性乳酸杆菌、金黄色葡萄球菌以及某些情况下抑制土拉菌生长的能力。其中 15 种化合物对一种或多种受试菌株显示出良好的抗菌活性（MIC < 5 µg/ml），最佳 MIC 值小于 0.8 µg/ml。所有这些化合物都具有良好的选择性，对 HepG2 细胞的细胞毒性最小。对六种可以结晶的化合物进行了结构解析，结果表明至少产生了两类基于吲哚的三聚体。其中一类化合物是天然产物 2,2-双（3-吲哚基）吲哚肟的取代衍生物。另一类化合物被归类为类色素化合物，所有这些化合物都在色素的第 11 位连接了多环悬垂基团。其中一个特别令人感兴趣的化合物 SAB-J85 的结构表明，任何具有可被加氧酶激活的环状结构的化合物都可以作为组合生物催化的底物。
• Nano Au/Pd-catalysed ‘on-water’ synthesis of C3–C3′ diaryl-oxindole scaffolds <i>via</i> N₂-selective dearomatization of indole
  作者：Shivanee Borpatra Gohain、Monika Basumatary、Purna K. Boruah、Manash R. Das、Ashim Jyoti Thakur

  DOI：10.1039/c9gc02370d

  日期：——

  Pd-rGO and Au–Pd-rGO nanocomposite catalysts were synthesized using microwave ‘on-water’. The catalysts were applied in the synthesis of 2,2-bis(indol-3-yl)indolin-3-ones). Comparatively, Au–Pd-rGO nanocomposite showed better activity.

  使用微波“在水上”合成了Pd-rGO和Au–Pd-rGO纳米复合催化剂。这些催化剂被应用于合成2,2-双(吲哚-3-基)吲哚-3-酮。相比之下，Au–Pd-rGO纳米复合催化剂表现出更好的活性。