2-(N-phthalimido)furan | 30739-23-2

• 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-(N-phthalimido)furan
• 英文别名: 2-N-phthaloylfuran；2-(furan-2-yl)isoindoline-1,3-dione；N--phthalimid；N-(2-Furyl)-phthalimid；N-furan-2-yl-phthalimide；2-(Furan-2-yl)isoindole-1,3-dione
• CAS: 30739-23-2
• 化学式: C₁₂H₇NO₃
• 分子量: 213.192
• InChiKey: QYOUAGPNQODNRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 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：
  50.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(N-phthalimido)furan 、 肼 生成 邻苯二甲酰肼
  参考文献：
  名称：

  REISCH J.; LABITZKE H., ARCH. PHARM. , 1975, 308, NO 9, 713-716

  摘要：

  DOI：
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成 2-(N-phthalimido)furan
  参考文献：
  名称：

  N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C–H Amination of Arenes and Heteroarenes

  摘要：

  This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.

  DOI：

  10.1021/ja501906x

文献信息

• Direct C–H amination reactions of arenes with <i>N</i>-hydroxyphthalimides catalyzed by cuprous bromide
  作者：Dongming Zhang、Bin Lv、Pan Gao、Xiaodong Jia、Yu Yuan

  DOI：10.3762/bjoc.18.65

  日期：——

  An efficient Cu-catalyzed strategy for the direct C–H amination of arenes in high yields using N-hydroxyphthalimide as the amidyl radical precursor under air is reported. A possible mechanism is proposed that proceeds via a radical reaction in the presence of CuBr and triethyl phosphite.

  报道了一种使用N-羟基邻苯二甲酰亚胺作为酰胺基自由基前体在空气下以高产率直接 C-H 胺化芳烃的有效 Cu 催化策略。提出了一种可能的机制，即在 CuBr 和亚磷酸三乙酯存在下通过自由基反应进行。
• Visible-Light-Driven C–H Imidation of Arenes and Heteroarenes by a Phosphonium Ylide Organophotoredox Catalyst: Application to C–H Functionalization of Alkenes
  作者：Yasunori Toda、Toya Kobayashi、Fumiya Hirai、Takamichi Yano、Makoto Oikawa、Kimiya Sukegawa、Masahiro Shimizu、Fuyuki Ito、Hiroyuki Suga

  DOI：10.1021/acs.joc.3c00988

  日期：2023.7.7

  Phosphonium ylide catalysis through an oxidative quenching cycle has been developed for visible-light-driven C–H imidation of arenes and heteroarenes. The present protocol could be applied not only to trihalomethylative lactonization reactions involving trifluoromethyl, trichloromethyl, and tribromomethyl radicals but also to the first example of an organophotoredox-catalyzed imidative lactonization

  通过氧化猝灭循环的鏻叶立德催化已被开发用于可见光驱动的芳烃和杂芳烃的 C-H 酰亚胺化。本协议不仅适用于涉及三氟甲基、三氯甲基和三溴甲基自由基的三卤甲基内酯化反应，而且适用于涉及以氮为中心的亲电子自由基物种的有机光氧化还原催化的亚胺化内酯化反应的第一个例子。
• <i>N</i>-Aminopyridinium Salts as Precursors for N-Centered Radicals – Direct Amidation of Arenes and Heteroarenes
  作者：Tobias W. Greulich、Constantin G. Daniliuc、Armido Studer

  DOI：10.1021/ol503338b

  日期：2015.1.16

  Readily prepared N-aminopyridinium salts are valuable precursors for the generation of N-centered radicals. Reduction of these salts by single electron transfer allows for clean generation of amidyl radicals. It is shown that direct radical C-H amination of heteroarenes and arenes can be achieved with N-aminopyridinium salts under mild conditions by using photoredox catalysis.
• [EN] ELECTROACTIVE CHEMILUMINESCENT COMPOUNDS FOR DETECTING BLOOD IN FORENSIC SCIENCE<br/>[FR] COMPOSÉS CHIMIOLUMINESCENTS ÉLECTROACTIFS POUR LA DÉTECTION DE SANG EN CRIMINALISTIQUE
  申请人：ORTA DOGU TEKNIK UNIV

  公开号：WO2021137825A1

  公开（公告）日：2021-07-08

  Chemiluminescence, or chemical luminescence, is the condition of a very small amount of thermal radiation and light radiation as a consequence of the chemical reaction that takes place in the substance. The luminol compound known in the literature is a chemiluminescent substance and is usually used in various applications. Luminol is an acyl-hydrazide ring and it contains the typical properties of this class. Its properties such as photo and thermal stability and chemical behavior in protic polar environments make this substance a good candidate in forensic science. When some important disadvantages of luminol (insolubility, low luminous quantum efficiency (1%) and misleading results in tests and/or disrupting the biologically active (DNA, etc.) structure in the sample being studied, etc.) are taken into consideration, new compounds that are designed so as to eliminate these disadvantages have great importance. It is required to use equally effective markers so as to make effective imaging, especially at the scene of a crime in forensic science. It is considered that this problem will be eliminated by means of these compounds. If the compounds designed in the same manner (different from luminol) only respond to iron ions, the fact about the images taken at the scene of a crime is based on blood samples will be obtained in a more evidential manner/with more clear evidence. After this study, the chemiluminescent radiation sensitivity of the compounds (especially for the detection of blood findings on the scene in forensic cases) to hemin and blood samples will be analyzed.