2-(2-(4-fluorophenyl)-2-oxoethoxy)isoindoline-1,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-(4-fluorophenyl)-2-oxoethoxy)isoindoline-1,3-dione
• 英文别名: 2-[2-(4-Fluorophenyl)-2-oxoethoxy]isoindole-1,3-dione；2-[2-(4-fluorophenyl)-2-oxoethoxy]isoindole-1,3-dione
• 化学式: C₁₆H₁₀FNO₄
• 分子量: 299.258
• InChiKey: QFLSLXBAYTWAHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2-(4-fluorophenyl)-2-hydroperoxyethoxy)isoindoline-1,3-dione 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以91%的产率得到2-(2-(4-fluorophenyl)-2-oxoethoxy)isoindoline-1,3-dione
  参考文献：
  名称：

  Visible-light- induced aerobic dioxygenation of styrenes under metal- and additive-free ambient conditions

  摘要：

  Visible light promoted hydroperoxidation of styrenes using hydroxylamine and molecular oxygen from air under metal-free and additive-free conditions at room temperature is described. Hydroperoxides were further converted into corresponding hydroxy compounds and a-oxygenated ketones in high yields under ambient conditions. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.12.073

文献信息

• Catalyst-Controlled Dioxygenation of Olefins: An Approach to Peroxides, Alcohols, and Ketones
  作者：Xiao-Feng Xia、Su-Li Zhu、Zhen Gu、Haijun Wang、Wei Li、Xiang Liu、Yong-Min Liang

  DOI：10.1021/acs.joc.5b00460

  日期：2015.6.5

  An efficient catalytic approach for the synthesis of substituted peroxides, alcohols, and ketones through a catalyst-controlled highly selective dioxygenation of olefins has been demonstrated. The reported methods are mild and practical, can be switched by the selection of different catalytic systems, and employ peroxide as an oxidant and a reagent at room temperature.

  已经证明了通过催化剂控制的烯烃的高选择性双加氧作用来合成取代的过氧化物，醇和酮的有效催化方法。报道的方法温和实用，可以通过选择不同的催化系统进行切换，并在室温下使用过氧化物作为氧化剂和试剂。
• Selectfluor-mediated highly selective radical dioxygenation of alkenes
  作者：Yunhe Lv、Xin Wang、Hao Cui、Kai Sun、Weiya Pu、Gang Li、Yingtao Wu、Jialin He、Xiaoran Ren

  DOI：10.1039/c6ra16266e

  日期：——

  A practical and simple selectfluor mediated highly selective radical dioxygenation of alkenes was achieved under mild conditions. Various hydroxylamines, such as N-Hydroxyphthalimide (NHPI), N-hydroxybenzotriazole (HOBt) and N-hydroxysuccinimide (NHSI), could react...

  在温和的条件下实现了实用且简单的selectfluor介导的烯烃的高选择性自由基双加氧反应。各种羟胺，例如N-羟基邻苯二甲酰亚胺（NHPI），N-羟基苯并三唑（HOBt）和N-羟基琥珀酰亚胺（NHSI）可以反应...
• Iron-Catalyzed Regioselective Oxo- and Hydroxy-Phthalimidation of Styrenes: Access to α-Hydroxyphthalimide Ketones
  作者：Ji-zong Zhang、Yu Tang

  DOI：10.1002/adsc.201500732

  日期：2016.3.3

  This paper describes the aerobic oxidation of styrenes catalyzed by iron(III) chloride (FeCl3) to form β‐keto‐N‐alkoxyphthalimides in fair to good yields. This oxidative process employs mild conditions with green and atom efficient dioxygen (O2) as the oxidant.

  本文介绍了氯化铁（III）（FeCl 3）催化的苯乙烯的需氧氧化，以相当高的收率形成β-酮-N-烷氧基邻苯二甲酰亚胺。该氧化过程采用温和的条件，绿色和原子有效的双氧（O 2）作为氧化剂。
• Electrochemical Oxidative Difunctionalization of Alkenes to Access α-Oxygenated Ketones
  作者：Changhui Dai、Yijie Shen、Yifan Wei、Ping Liu、Peipei Sun

  DOI：10.1021/acs.joc.1c01831

  日期：2021.10.1

  Dioxygenation of alkenes was developed by the combination of electrochemical synthesis and aerobic oxidation, leading to easy accessibility of α-oxygenated ketones in an eco-friendly fashion. Using air as the oxygen source and the absence of transition metals were the critical features of this protocol. A wide range of alkenes and N-hydroxyimides were found to be compatible and provided α-oxygenated

  烯烃的双氧化是通过电化学合成和有氧氧化相结合开发的，从而以环保的方式轻松获得 α-氧化酮。使用空气作为氧源和没有过渡金属是该协议的关键特征。发现范围广泛的烯烃和N-羟基酰亚胺是相容的，并以中等至高产率提供 α-氧化酮。
• Cobalt Catalyst‐Controlled Selective Dioxygenation of Styrenes Using <i>N‐</i> Hydroxyphthalimide with Molecular Oxygen
  作者：Xiaosong Hao、Huihui Ji、Hongju Zhan、Qian Zhang、Dong Li

  DOI：10.1002/adsc.202100921

  日期：2022.1.4

  A cobalt-catalyzed selective dioxygenation of styrenes with N-hydroxyphthalimide (NHPI) was developed using molecular oxygen as the terminal oxidant. Alcohol and ketone products can be selectively formed from identical substrates by catalyst control. The reaction was applicable to a broad range of styrenes and exhibited good functional group tolerance. It provided a method for preparation of 1,2-diol

  使用分子氧作为末端氧化剂开发了一种钴催化的苯乙烯与N-羟基邻苯二甲酰亚胺(NHPI) 的选择性双氧化反应。醇和酮产品可以通过催化剂控制由相同的底物选择性地形成。该反应适用于范围广泛的苯乙烯，并表现出良好的官能团耐受性。提供了一种制备1,2-二醇或α-羟基酮衍生物的方法。