2-(isochroman-1-yloxy)isoindoline-1,3-dione | 1034621-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(isochroman-1-yloxy)isoindoline-1,3-dione
• 英文别名: 2-(3,4-dihydro-1H-isochromen-1-yloxy)isoindole-1,3-dione
• CAS: 1034621-96-9
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: XFVPULPQSNBFPA-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  481.1±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(isochroman-1-yloxy)isoindoline-1,3-dione 在 一水合肼 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 16.0h， 以67.1%的产率得到
  参考文献：
  名称：

  Organocatalyzed cross-dehydrogenative coupling for C(sp3)–O bonds formation: a rapid access to α-aminoxyl isochromans

  摘要：

  Tetrabutyl ammonium iodide catalyzed cross-dehydrogenative coupling reaction between -C(sp(3))-H of isochromans and N-hydroxyphathalimide has been achieved using tert-butylhydroxyperoxide as theterminal oxidant. This method offers rapid access to prevalent -aminoxyl isochroman architectures. A diverse of synthetic isochromans was tolerated with this protocol, giving the corresponding product in moderate to good yields.[GRAPHICS].

  DOI：

  10.1007/s10562-018-2640-9
• 作为产物：
  描述：

  苯酐 在 盐酸羟胺 、 sodium acetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(isochroman-1-yloxy)isoindoline-1,3-dione
  参考文献：
  名称：

  Formation of C–O Bond via Cross-Dehydrogenative Coupling between Isochroman and Oxime under Metal-Free Oxidation Conditions

  摘要：

  DDQ-mediated C-O bond formation through cross-dehydrogenative coupling (CDC) reaction without any metal catalyst under mild conditions was developed. Series of isochromans and oximes could be employed as substrates, and the products were obtained in good yields.

  DOI：

  10.1055/s-0032-1317960

文献信息

• Photoinduced Electron-Transfer-Promoted Redox Fragmentation of <i>N</i>-Alkoxyphthalimides
  作者：Maria Zlotorzynska、Glenn M. Sammis

  DOI：10.1021/ol202740w

  日期：2011.12.2

  new photoinduced electron-transfer-promoted redox fragmentation of N-alkoxyphthalimides has been developed. Mechanistic experiments have established that this reaction proceeds through a unique concerted intramolecular fragmentation process. This distinctive mechanism imparts many synthetic advantages, which are highlighted in the redox fragmentation of various heterocyclic substrates.

  已经开发了一种新的光诱导的N-烷氧基邻苯二甲酰亚胺电子转移促进的氧化还原片段化。机理实验已经确定，该反应通过独特的协同分子内断裂过程进行。这种独特的机理赋予了许多合成优势，这些优势在各种杂环底物的氧化还原片段化中得到了彰显。
• Transition-Metal-Free Oxidative Aminooxyarylation of Alkenes: Annulations toward Aminooxylated Oxindoles
  作者：Ming-Zhong Zhang、Na Luo、Rui-Yang Long、Xian-Tao Gou、Wen-Bing Shi、Shu-Hua He、Yong Jiang、Jin-Yang Chen、Tieqiao Chen

  DOI：10.1021/acs.joc.7b02740

  日期：2018.2.16

  An efficient oxidative aminooxyarylation of alkenes under a transition-metal-free condition was described. Under the reaction conditions, N-hydroxyphthalimide (NHPI) reacted readily with N-arylacrylamides to produce cyclic products via a radical C–H functionalization process, achieving both C–O and C–C bonds formation in one pot. This reaction provided a facile access to the valuable aminooxylated

  描述了在无过渡金属条件下烯烃的有效氧化氨基氧基化。在反应条件下，N-羟基邻苯二甲酰亚胺（NHPI）与N-芳基丙烯酰胺容易反应，通过自由基CH-H官能化过程生成环状产物，从而在一锅中同时形成C-O和C-C键。该反应提供了容易获得有价值的氨基氧基化的吲哚的途径。在反应条件下，苄基和α-亚甲基C（sp 3）-H键也被氨氧基化。
• Ultrasound accelerated synthesis of <i>O</i>-alkylated hydroximides under solvent- and metal-free conditions
  作者：Hongmei Jiang、Xiaoyue Tang、Sihan Liu、Lian Wang、Haicheng Shen、Jiankui Yang、Huixian Wang、Qing-Wen Gui

  DOI：10.1039/c9ob02245g

  日期：——

  A novel, sustainable, environmentally friendly, solvent-free and metal catalyst-free method for the CDC reaction between NHPI and benzyl/ether compounds is described.

  描述了一种新颖、可持续、环保、无溶剂和无金属催化剂的方法，用于NHPI和苄基/醚化合物之间的CDC反应。
• Cu-Facilitated C−O Bond Formation Using <i>N</i>-Hydroxyphthalimide: Efficient and Selective Functionalization of Benzyl and Allylic C−H Bonds
  作者：Ji Min Lee、Eun Ju Park、Seung Hwan Cho、Sukbok Chang

  DOI：10.1021/ja8031218

  日期：2008.6.1

  A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and Phl(OAc)(2) in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals.