2-nitro-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde | 272789-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-nitro-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde
• 英文别名: 2-Nitro-5-(oxan-2-yloxy)benzaldehyde
• CAS: 272789-37-4
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: DNIVJVJQGVAHPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-nitro-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde 在 palladium on activated charcoal 盐酸 、 重铬酸吡啶 、 正丁基锂 、 氢气 、 乙酸酐 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 17.75h， 生成 5-hydroxy-2-formamidophenyl-2'-thiazolylketone
  参考文献：
  名称：

  Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani

  摘要：

  The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5-hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00479-3
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 5-羟基-2-硝基苯甲醛 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以60%的产率得到2-nitro-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde
  参考文献：
  名称：

  设计和合成用于抗体催化的有机磷神经毒剂水解的α，α-二氟次膦酸酯半抗原。

  摘要：

  在安全中和有机磷化学武器的一种新方法中，我们设计了一种半抗原，以诱导具有磷酸酶活性的催化抗体。在这里，我们报告该α，α-二氟次膦半抗原6的合成。讨论了将关键的α，α-二氟甲基特征引入次膦酸酯半抗原的各种方法。用亲电的宝石二氟化剂N-氟苯磺酰亚胺可获得最佳结果。

  DOI：

  10.1002/(sici)1521-3765(20000317)6:6<1050::aid-chem1050>3.0.co;2-5

文献信息

• Synthesis and peripheral substituent effects of bay-annulated indigo derivatives
  作者：Taniyuki Furuyama、Daichi Tamura、Hajime Maeda、Masahito Segi

  DOI：10.1016/j.tetlet.2018.06.036

  日期：2018.7

  study, indolo-naphthyridine-6,13-diones (5a–d) with four different peripheral substituents were prepared via bay-annulation reactions of indigo. The resulting compounds (5a–d) exhibited fluorescence in the red to near-IR region, while the parent indigo molecule showed no fluorescence. Although the peripheral substituents were oriented to the exterior of the π-conjugated system, the electronic structure

  在这项研究中，通过靛蓝的湾环化反应制备了具有四个不同外围取代基的吲哚-萘啶-6,13-​​二酮（5a–d）。所得化合物（5a–d）在红色至近红外区域显示荧光，而母体靛蓝分子未显示荧光。尽管外围取代基定向于π共轭体系的外部，但电子结构影响了吸收光谱和荧光光谱。此外，计算的分子轨道和吸收光谱成功地再现了实验吸收光谱和循环伏安图。
• ORGANIC SEMICONDUCTOR POLYMERS
  申请人：BRONSTEIN HUGO

  公开号：US20180287066A1

  公开（公告）日：2018-10-04

  The organic semiconductor polymers relate to polymers containing an indolo-naphthyridine-6,13-dione thiophene (INDT) chromophore. The organic semiconductor polymers are formed by polymerizing INDT monomer with thiophene to obtain a conjugated polymer of the chromophore linked by thiophene monomers (INDT-T), with phenyl to obtain a conjugated polymer of the chromophore linked by phenyl monomers (INDT-P), with selenophene to obtain a conjugated polymer of the chromophore linked by selenophene monomers (INDT-S), or with benzothiadazole to obtain a conjugated polymer of the chromophore linked by benzothiadazole monomers (INDT-BT).

  有机半导体聚合物涉及含有吲哚萘啉-6,13-二酮噻吩（INDT）色团的聚合物。有机半导体聚合物通过将INDT单体与噻吩聚合得到由噻吩单体连接的色团的共轭聚合物（INDT-T），与苯聚合得到由苯单体连接的色团的共轭聚合物（INDT-P），与硒吩聚合得到由硒吩单体连接的色团的共轭聚合物（INDT-S），或者与苯并噻唑聚合得到由苯并噻唑单体连接的色团的共轭聚合物（INDT-BT）。
• Organic semiconductor polymers
  申请人：Bronstein Hugo

  公开号：US10547005B2

  公开（公告）日：2020-01-28

  The organic semiconductor polymers relate to polymers containing an indolo-naphthyridine-6,13-dione thiophene (INDT) chromophore. The organic semiconductor polymers are formed by polymerizing INDT monomer with thiophene to obtain a conjugated polymer of the chromophore linked by thiophene monomers (INDT-T), with phenyl to obtain a conjugated polymer of the chromophore linked by phenyl monomers (INDT-P), with selenophene to obtain a conjugated polymer of the chromophore linked by selenophene monomers (INDT-S), or with benzothiadazole to obtain a conjugated polymer of the chromophore linked by benzothiadazole monomers (INDT-BT).

  有机半导体聚合物涉及含有吲哚-萘啶-6,13-二酮噻吩（INDT）发色团的聚合物。这些有机半导体聚合物的形成方法如下：INDT 单体与噻吩聚合，得到由噻吩单体连接的发色团共轭聚合物（INDT-T）；INDT 单体与苯基聚合，得到由苯基单体连接的发色团共轭聚合物（INDT-P）、与硒吩一起获得由硒吩单体连接的发色团共轭聚合物（INDT-S），或与苯并噻二唑一起获得由苯并噻二唑单体连接的发色团共轭聚合物（INDT-BT）。
• A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells
  作者：Kealan J. Fallon、Nilushi Wijeyasinghe、Nir Yaacobi-Gross、Raja S. Ashraf、David M. E. Freeman、Robert G. Palgrave、Mohammed Al-Hashimi、Tobin J. Marks、Iain McCulloch、Thomas D. Anthopoulos、Hugo Bronstein

  DOI：10.1021/acs.macromol.5b00542

  日期：2015.8.11

  A novel, highly soluble chromophore for use in organic electronics based on an indigoid structure is reported. Copolymerization with thiophene affords an extremely narrow band gap polymer with a maximum absorption at similar to 800 nm. The novel polymer exhibits high crystallinity and high ambipolar transport in OFET devices of 0.23 cm(2) V-1 s(-1) for holes and 0.48 cm(2) V-1 s(-1) for electrons. OPV device efficiencies up to 2.35% with light absorbance up to 950 nm demonstrate the potential for this novel chromophore in near-IR photovoltaics.