2-(2-(4-methoxyphenyl)-2-oxoethoxy)isoindoline-1,3-dione | 1262623-27-7

• 英文名称: 2-(2-(4-methoxyphenyl)-2-oxoethoxy)isoindoline-1,3-dione
• 英文别名: 2-[2-(4-methoxyphenyl)-2-oxoethoxy]isoindoline-1,3-dione；N-(2-oxo-2-(p-methoxyphenyl)ethoxy)phthalimide
• CAS: 1262623-27-7
• 化学式: C₁₇H₁₃NO₅
• 分子量: 311.294
• InChiKey: PCCKWDOCWPYFPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(2-(4-methoxyphenyl)-2-oxoethoxy)isoindoline-1,3-dione 400.0 ℃ 、1.33 Pa 条件下， 反应 -6.0h， 以49%的产率得到2-(4-甲氧基苯基)-2-氧代乙醛
  参考文献：
  名称：

  N-烷氧基邻苯二甲酰亚胺气相热解为功能取代的醛：动力学和机理研究

  摘要：

  在 400-500 o C 和 0.02 Torr 条件下，伯 N-烷氧基邻苯二甲酰亚胺的快速真空热解 (FVP) 得到官能取代的醛。基于动力学数据和产物分析提出了这种热解转化的机制。

  DOI：

  10.3998/ark.5550190.0011.a13
• 作为产物：
  描述：

  2-(2-hydroperoxy-2-(4-methoxyphenyl)ethoxy)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88%的产率得到2-(2-(4-methoxyphenyl)-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

• 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。
• Copper(II)-Catalyzed Direct Dioxygenation of Alkenes with Air and <i>N</i>-Hydroxyphthalimide: Synthesis of β-Keto-<i>N</i>-alkoxyphthalimides
  作者：Raghunath Bag、Dinabandhu Sar、Tharmalingam Punniyamurthy

  DOI：10.1021/acs.orglett.5b00770

  日期：2015.4.17

  Copper(II)-catalyzed direct dioxygenation of alkenes using air and a simple N-hydroxyphthalimide leading to beta-keto-N-alkoxyphthalimides has been developed. The reaction system is mild, efficient, and effective at room temperature with broad substrate scope and substantial steric hindrance. The radical-trapping and O-18-labeling experiments have been demonstrated.