N-(2-hydroxybicyclo<2.2.1>heptan-2-yloxy)phtalimide | 125349-05-5

• 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: N-(2-hydroxybicyclo<2.2.1>heptan-2-yloxy)phtalimide
• 英文别名: N-(2-hydroxybicyclo<2.2.2>heptan-2-yloxy)phthalimide；N-(2-Hydroxybicyclo<2.2.1>heptan-3-yloxy)phthalimide；2-((3-hydroxybicyclo[2.2.1]heptan-2-yl)oxy)isoindoline-1,3-dione；2-[(3-Hydroxybicyclo[2.2.1]heptan-2-yl)oxy]-1H-isoindole-1,3(2H)-dione；2-[(3-hydroxy-2-bicyclo[2.2.1]heptanyl)oxy]isoindole-1,3-dione
• CAS: 125349-05-5
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: NJVAJXJOGXARJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-Hydroperoxybicyclo<2.2.1>heptan-2-yloxy)phthalimide 在 三苯基膦 作用下， 以83%的产率得到N-(2-hydroxybicyclo<2.2.1>heptan-2-yloxy)phtalimide
  参考文献：
  名称：

  Novel Catalysis by N-Hydroxyphthalimide in the Oxidation of Organic Substrates by Molecular Oxygen

  摘要：

  DOI：

  10.1021/jo00118a002

文献信息

• 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。
• Alkane Oxidation with Molecular Oxygen Using a New Efficient Catalytic System:  <i>N</i>-Hydroxyphthalimide (NHPI) Combined with Co(acac)<i>_n</i> (<i>n</i> = 2 or 3)
  作者：Yasutaka Ishii、Takahiro Iwahama、Satoshi Sakaguchi、Kouichi Nakayama、Yutaka Nishiyama

  DOI：10.1021/jo951970l

  日期：1996.1.1

  A novel class of catalysts for alkane oxidation with molecular oxygen was examined. N-Hydroxyphthalimide (NHPI) combined with Co(acac)(n)() (n = 2 or 3) was found to be an efficient catalytic system for the aerobic oxidation of cycloalkanes and alkylbenzenes under mild conditions. Cycloalkanes were successfully oxidized with molecular oxygen in the presence of a catalytic amount of NHPI and Co(acac)(2)

  研究了用于用分子氧氧化烷烃的新型催化剂。发现N-羟基邻苯二甲酰亚胺（NHPI）与Co（acac）（n）（）（n = 2或3）结合是在温和条件下好氧氧化环烷烃和烷基苯的有效催化体系。在催化量的NHPI和Co（acac）（2）的存在下于100摄氏度的乙酸中，成功地用分子氧将环烷烃氧化，得到相应的环烷酮和二羧酸。使用该催化系统，烷基苯也被双氧氧化。例如，在这些条件下，甲苯以优异的产率转化为苯甲酸。乙苯和丁苯在其α位置被选择性氧化，分别以良好的收率分别形成相应的酮，苯乙酮和1-苯基-1-丁酮。该氧化的关键中间体被认为是由NHPI和分子氧使用Co（II）物质生成的邻苯二甲酰亚胺N-氧基。使用NHPI / Co（acac）（2）用氧气将乙苯和乙苯-d（10​​）氧化时的同位素效应（k（H）/ k（D））为3.8。
• Epoxidation catalysed by Mn III TPPCl using dioxygen activated by a system containing N-hydroxyphthalimide and styrene, 2-norbornene or indene
  作者：Shigeko Ozaki、Tomomi Hamaguchi、Keiichi Tsuchida、Yukio Kimata、Masaichiro Masui

  DOI：10.1039/p29890000951

  日期：——

  The catalytic epoxidation of alkenes by molecular oxygen activated in the system containing N-hydroxyphthalimide (NHPI) and active alkenes such as styrene, 2-norbornene or indene is reported. The transient intermediates, alkyl hydroperoxides formed by autoxidation of NHPI and the active alkenes are proposed as oxygen sources which transfer mono-oxygen to MnIIITPPCl.

  据报道，烯烃在含N-羟基邻苯二甲酰亚胺（NHPI）和活性烯烃（如苯乙烯，2-降冰片烯或茚）的体系中被分子氧活化而催化环氧化。提出了过渡中间体，通过NHPI的自氧化形成的烷基氢过氧化物和活性烯烃作为将单氧转移到Mn III TPPCl的氧源。