2-(4-chlorophenyl)-1-oxy-indol-3-one | 69511-79-1

• 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: 2-(4-chlorophenyl)-1-oxy-indol-3-one
• 英文别名: 2-(4-chloro-phenyl)-1-oxy-indol-3-one；2-(4-chloro-phenyl)-indol-3-one-1-oxide；2-(4-Chlor-phenyl)-indol-3-on-1-oxid；2-(4-Chlorphenyl)-isatogen；3H-Indol-3-one, 2-(4-chlorophenyl)-, 1-oxide；2-(4-chlorophenyl)-1-oxidoindol-1-ium-3-one
• CAS: 69511-79-1
• 化学式: C₁₄H₈ClNO₂
• 分子量: 257.676
• InChiKey: XOMOLSDIXFIBAL-UHFFFAOYSA-N

物化性质

• 熔点：
  177.0-177.1 °C
• 沸点：
  453.4±47.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-1-oxy-indol-3-one 在 indium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以78%的产率得到2-(4-chlorophenyl)-3H-indol-3-one
  参考文献：
  名称：

  2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities

  摘要：

  The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2(4-dimethylaminophenyl)-5-methoxy-indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.059
• 作为产物：
  描述：

  (4-氯苯乙炔基)三甲基硅烷 在 bis-triphenylphosphine-palladium(II) chloride 、 双(乙腈)氯化钯(II) 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-(4-chlorophenyl)-1-oxy-indol-3-one
  参考文献：
  名称：

  2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities

  摘要：

  The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2(4-dimethylaminophenyl)-5-methoxy-indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.059

文献信息

• C–H alkenylation/cyclization and sulfamidation of 2-phenylisatogens using <i>N</i>-oxide as a directing group
  作者：Lingmei Guo、Baolan Tang、Ruifang Nie、Yanzhao Liu、Shan Lv、Huijing Wang、Li Guo、Li Hai、Yong Wu

  DOI：10.1039/c9cc05719f

  日期：——

  first example of transition-metal-catalyzed C–H activations of 2-phenylisatogens with alkynes and sulfonyl azides has been developed using N-oxide as the directing group. Ru(II)-Catalyzed C–H alkenylation/cyclization and Ir(III)-catalyzed direct C–H sulfamidation proceeded with good yields and excellent functional group tolerance. Importantly, these two transformations provided straightforward routes

  利用炔烃和磺酰叠氮化物开发了第一个过渡金属催化的2-苯基致病菌C–H活化的炔烃和磺酰基叠氮化物的例子是使用N-氧化物作为指导基团。Ru（II）催化的C–H烯基化/环化反应和Ir（III）催化的直接C–H磺酰胺化反应具有良好的收率和出色的官能团耐受性。重要的是，这两个转化分别为吲哚-3-酮衍生物和磺酰胺化的2-苯基异硫氰酸酯的合成提供了直接的途径，这可能具有相当大的生物活性。
• 一种通过C-H活化磺酰胺化2-苯基异靛红的新方法
  申请人：四川大学

  公开号：CN110317160B

  公开（公告）日：2022-07-05

  本发明涉及一种以磺酰叠氮为偶联试剂，通过过渡金属催化芳基C‑H活化反应，对2‑苯基异靛红进行磺酰胺化，构建2‑苯基异靛红衍生物的新方法。本发明相比于传统技术，官能团耐受性好，收率高；低温，安全方便，具有广阔的应用前景；副产物仅为氮气，避免了产生大量的副产物，提高了原子利用率；无需进行底物的预活化，反应条件温和并且反应时间短，降低了操作难度。
• Oxygenation of 2,3-dihydroindoles
  作者：Johnny Slätt、Jan Bergman

  DOI：10.1016/s0040-4020(02)01198-5

  日期：2002.11

  properties and development of a general method to construct these derivatives has now been developed. Indolines (2,3-dihydroindoles) and isatogens have been prepared in an efficient route starting from indoles substituted in position 2. Reduction of the 2-substituted indoles was performed with tin and hydrochloric acid to give racemic indolines, which were converted to isatogens by 3-chloroperoxybenzoic

  异构原（3-氧代-3 H-吲哚-1-氧化物）具有令人感兴趣的生物学特性，目前已经开发出构建这些衍生物的通用方法。吲哚啉（2,3-二氢吲哚）和异氰酸酯是从第2位取代的吲哚开始以有效途径制备的。用锡和盐酸还原2-取代的吲哚可得到外消旋的吲哚，然后通过外消旋的吲哚将其转化为isatogens。 3-氯过氧苯甲酸（m -CPBA）。
• 一种合成1,2-二氢-3H-吲哚-3-酮衍生物的新方法
  申请人：四川大学

  公开号：CN110256332B

  公开（公告）日：2022-07-05

  本发明涉及一种合成1,2‑二氢‑3H‑吲哚‑3‑酮的新方法。以2‑苯基异靛红与炔类化合物为原料，通过过渡金属催化的C‑H活化/环合反应在芳环上形成C‑C键并与异靛红2位环合成1,2‑二氢‑3H‑吲哚‑3‑酮衍生物。与传统方法相比，本方法的优势如下：（1）步骤简单，底物适用范围广，反应产率高。（2）能选择性地得到单一构型的产物，安全方便，具有广阔的应用前景。
• Regioselective Cross-Coupling of Isatogens with Boronic Acids to Construct 2,2-Disubstituted Indolin-3-one Derivatives
  作者：Hetao Xu、Mingxing Ye、Kai Yang、Qiuling Song

  DOI：10.1021/acs.orglett.1c02808

  日期：2021.10.15

  Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron “ate” complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with excellent regioselectivity, which exhibit operational simplicity, good functional group tolerance, and a broad substrate scope.

  在本文中，我们通过硼“ate”配合物的 1,4-金属盐转移，提出了一种无过渡金属的交叉偶联反应，即靛蓝原与硼酸。这种偶联反应提供了一种可行的方法来提供有价值的 2,2-二取代 indolin-3-one 衍生物，具有优异的区域选择性，具有操作简单、良好的官能团耐受性和广泛的底物范围。