2-(4-chlorophenyl)-3H-indol-3-one

• 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)-3H-indol-3-one
• 英文别名: 2-(4-Chlorophenyl)indol-3-one
• 化学式: C₁₄H₈ClNO
• 分子量: 241.677
• InChiKey: JFHTUMSONBAJDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 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：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-3H-indol-3-one 在 sodium tetrahydroborate 、 L-脯氨酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 (2S)-2-(4-chlorophenyl)-2-(2-hydroxyethyl)-2,3-dihydro-1H-indol-3-one
  参考文献：
  名称：

  醛向3H-吲哚-3-酮的不对称脯氨酸催化加成反应：带有季位立体中心的2,3-二氢-1H-吲哚-3-酮的对映选择性合成

  摘要：

  脯氨酸催化的各种脂肪族醛加成到位阻2-芳基取代的3 H-吲哚-3-酮中，可得到具有出色对映选择性的2,2-二取代的2,3-二氢1 H-吲哚-3-酮衍生物。此外，手性衍生物（S）-2-（2-溴苯基）-2,3-二氢-2-（2-羟乙基）-1 H-吲哚-3-酮的合成可以用作以高水平的对映选择性完成了制备天然产物辛克汀汀A的中间体。

  DOI：

  10.1002/hlca.201200498
• 作为产物：
  描述：

  (4-氯苯乙炔基)三甲基硅烷 在 indium(III) chloride 、 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， 反应 3.0h， 生成 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

文献信息

• Multi-site cyclization via initial C–H activation using a rhodium(<scp>iii</scp>) catalyst: rapid assembly of frameworks containing indoles and indolines
  作者：Ji-Rong Huang、Liu Qin、Yu-Qin Zhu、Qiang Song、Lin Dong

  DOI：10.1039/c4cc07125e

  日期：——

  Tandem multi-site cyclization triggered by Rh(iii)-catalyzed C–H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization).

  通过Rh（III）催化的C–H活化触发的串联多位点环化反应已成功实现，用于高效合成螺环吲哚-3-酮（C2-环化）、苯并[a]咔唑（C3-环化）和一种不寻常的吲哧核心（N1-环化）。
• An asymmetric normal-electron-demand aza-Diels–Alder reaction via trienamine catalysis
  作者：Jing-Xin Liu、Qing-Qing Zhou、Jin-Gen Deng、Ying-Chun Chen

  DOI：10.1039/c3ob41698d

  日期：——

  An asymmetric normal-electron-demand aza-Diels–Alder cycloaddition of 2-aryl-3H-indol-3-ones and 2,4-dienals was explored via trienamine catalysis of a chiral secondary amine. Multifunctional tricyclic polyhydropyrido[1,2-a]indoles were efficiently constructed in good stereoselectivity (up to 92% ee, >19 : 1 dr).

  通过三烯胺催化手性仲胺探索了2-芳基-3 H-吲哚-3-酮和2,4-二烯的不对称正电子需求的氮杂-Diels-Alder环加成反应。多功能三环多氢吡啶并[1,2- a ]吲哚以良好的立体选择性（高达92％ee，> 19：1 dr）被有效地构建。
• Synthesis of <i>N</i> -Fused Seven-Membered Indoline-3-ones <i>via</i> a Palladium-Catalyzed One-Pot Insertion Reaction from 2-Alkynyl Arylazides and Cyclic <i>β</i> -Diketones
  作者：Ping Li、Rong Sheng、Zhiqiang Zhou、Guiwen Hu、Xiaoxiang Zhang

  DOI：10.1002/ejoc.202000243

  日期：2020.4.16

  A novel insertion reaction of cyclic C‐acylimines into cyclic β‐diketones to construct N‐fused seven‐membered multifunctional polycyclic indoline‐3‐one derivatives has been described, which has shown good tolerance of various functional groups. The corresponding products were obtained in moderate to good yields under mild reaction conditions.

  描述了一种新型的将环状C-酰亚胺插入环状β-二酮的新型反应，以构建N融合的七元多功能多环吲哚3-3-酮衍生物，显示出对各种官能团的良好耐受性。在温和的反应条件下，以中等至良好的产率获得了相应的产物。
• Organocatalytic asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality
  作者：Xi Yuan、Xudong Wu、Fei Peng、Haijun Yang、Changjin Zhu、Hua Fu

  DOI：10.1039/d0cc05432a

  日期：——

  An efficient method for chiral phosphoric acid-catalyzed asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality has been developed via the reaction of 3-arylindoles with 2-aryl-3H-indol-3-ones, and the target products were obtained in high yields with excellent enantioselectivity and diastereoselectivity.

  通过3-芳基吲哚与2-芳基-3 H-吲哚-3-酮的反应，开发了一种有效的手性磷酸催化不对称合成轴向和中心手性的芳基吲哚-3-酮的方法。以高收率获得具有优异的对映选择性和非对映选择性的目标产物。
• Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclic<i>C</i>-acylimines with simple ketones: facile access to C2-quaternary indolin-3-ones
  作者：Jin-Shan Li、Yong-Jie Liu、Shen Li、Jun-An Ma

  DOI：10.1039/c8cc05125a

  日期：——

  A chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction of simple ketones with cyclic C-acylimines has been established for the synthesis of C2-quaternary indolin-3-ones. In the presence of 5–10 mol% chiral phosphoric acid, a series of 2-(2-oxo-2-phenylethyl)-2-arylindolin-3-ones were obtained in good to high yield with up to 99% ee. The adducts obtained could be readily converted into

  建立了手性布朗斯台德酸催化的简单酮类与环状C-酰基亚胺的直接不对称曼尼希反应，用于合成C2-季吲哚-3-酮。在5-10 mol％手性磷酸的存在下，以高达99％ee的良好或高收率获得了一系列2-（2-氧代-2-苯基乙基）-2-芳基吲哚-3-酮。通过简单的修饰，可以容易地将获得的加合物转化为二氢吲哚，三环吲哚-3-酮和四环四氢吲哚并[1,2- a ]喹啉。