1-(4-(allyloxy)-3-nitrophenyl)ethan-1-one | 92288-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(allyloxy)-3-nitrophenyl)ethan-1-one
• 英文别名: 1-(4-(allyloxy)-3-nitrophenyl)ethanone；1-(3-Nitro-4-prop-2-enoxyphenyl)ethanone
• CAS: 92288-71-6
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: MVTVRQSHIAYKNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-(allyloxy)-3-nitrophenyl)ethan-1-one 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 以97%的产率得到1-(4-(allyloxy)-3-aminophenyl)ethan-1-one
  参考文献：
  名称：

  芳基胺的环化自由基碳碘化，碳基化和碳氨化

  摘要：

  报道了各种芳基胺的自由基碳碘化。由相应的芳基胺原位生成的芳基重氮盐与Bu 4 NI反应生成相应的芳基，这些芳基经过5-exo或6-exo环化。碘的提取最终以良好或优异的收率提供了碳碘化产品。如果添加TEMPO，则级联反应会提供环化的氨基碳酰化产物。在PhTeTePh存在下进行反应可得到苯基碲化的环化产物。

  DOI：

  10.1002/anie.201403968
• 作为产物：
  描述：

  4'-氟-3'-硝基苯乙酮 、 烯丙醇 在 三乙胺 作用下， 生成 1-(4-(allyloxy)-3-nitrophenyl)ethan-1-one
  参考文献：
  名称：

  Oelschlaeger,H. et al., Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1963, vol. 296, p. 107 - 120

  摘要：

  DOI：

文献信息

• Copper-Promoted Sandmeyer Trifluoromethylation Reaction
  作者：Jian-Jun Dai、Chi Fang、Bin Xiao、Jun Yi、Jun Xu、Zhao-Jing Liu、Xi Lu、Lei Liu、Yao Fu

  DOI：10.1021/ja404217t

  日期：2013.6.12

  A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.

  描述了芳香胺的铜促进的三氟甲基化反应。这种转化在温和条件下顺利进行，并且对许多合成相关的官能团表现出良好的耐受性。它为合成三氟甲基化芳烃和杂芳烃提供了一种替代方法。它也构成了桑德迈尔反应的一个新例子。
• Visible light-promoted carbodi(tri)fluoromethylthiolation of alkenes
  作者：Wengui Wang、Shuna Gao、Zhiying Ding、Weirui Zhu、Shuya Xing、Shuai Zhao、Xinxin Shao、Shoufeng Wang

  DOI：10.1016/j.jfluchem.2022.109949

  日期：2022.2
• A Ratiometric Acoustogenic Probe for <i>in Vivo</i> Imaging of Endogenous Nitric Oxide
  作者：Christopher J. Reinhardt、Effie Y. Zhou、Michael D. Jorgensen、Gina Partipilo、Jefferson Chan

  DOI：10.1021/jacs.7b10783

  日期：2018.1.24

  Photoacoustic (PA) imaging is an emerging imaging modality that utilizes optical excitation and acoustic detection to enable high resolution at centimeter depths. The development of activatable PA probes can expand the utility of this technology to allow for detection of specific stimuli within live-animal models. Herein, we report the design, development, and evaluation of a series of Acoustogenic Probe(s) for Nitric Oxide (APNO) for the ratiometric, analyte-specific detection of nitric oxide (NO) in vivo. The best probe in the series, APNO-5, rapidly responds to NO to form an N-nitroso product with a concomitant 91 nm hypsochromic shift. This property enables ratiometric PA imaging upon selective irradiation of APNO-5 and the corresponding product, tAPNO-S. Moreover, APNO-5 displays the requisite photophysical characteristics for in vivo PA imaging (e.g., high absorptivity, low quantum yield) as well as high biocompatibility, stability, and selectivity for NO over a variety of biologically relevant analytes. APNO-5 was successfully applied to the detection of endogenous NO in a murine lipopolysaccharide-induced inflammation model. Our studies show a 1.9-fold increase in PA signal at 680 run and a 1.3-fold ratiometric turn-on relative to a saline control.