1-(4-(allyloxy)-3-aminophenyl)ethan-1-one | 1215969-69-9

• 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-aminophenyl)ethan-1-one
• 英文别名: 1-(4-(allyloxy)-3-aminophenyl)ethanone；1-(3-Amino-4-prop-2-enoxyphenyl)ethanone；1-(3-amino-4-prop-2-enoxyphenyl)ethanone
• CAS: 1215969-69-9
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: LUYSEXDHBWMBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-(allyloxy)-3-aminophenyl)ethan-1-one 在 甲烷磺酸 、 四丁基碘化铵 、 亚硝酸异戊酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以97%的产率得到1-(3-(iodomethyl)-2,3-dihydrobenzofuran-5-yl)ethanone
  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'-羟基-3'-硝基苯乙酮 在 盐酸 、 tin(II) chloride dihdyrate 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 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

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。
• Intramolecular Radical Carboaminoxylation of Aryl Amines
  作者：Armido Studer、Marcel Hartmann、Carolin Gerleve

  DOI：10.1055/s-0035-1560770

  日期：——

  Cyclizing radical carboaminoxylation of various aryl amines is presented. The aryl diazonium salts in situ generated from the corresponding aryl amines are reduced by tetra-n-butylammonium iodide (TBAI) to give the corresponding aryl radicals. These aryl radicals undergo 5-exo and 6-exo cyclization. Subsequent trapping with TEMPO or various other nitroxides provides the corresponding cyclized carboaminoxylated

  介绍了各种芳胺的环化自由基羧基氧基化。由相应的芳胺原位生成的芳基重氮盐被四正丁基碘化铵 (TBAI) 还原，得到相应的芳基。这些芳基经历 5-exo 和 6-exo 环化。随后用 TEMPO 或各种其他氮氧化物捕集以中等至非常好的产率提供相应的环化羧基氨基氧化产物。
• The Trifluoromethylating Sandmeyer Reaction: A Method for Transforming CN into CCF₃
  作者：Duncan L. Browne

  DOI：10.1002/anie.201308997

  日期：2014.2.3

  trifluoromethylate: The beneficial properties imparted by the trifluoromethylation of aromatic compounds continue to drive the discovery of novel reagents and reactions for the late‐stage introduction of such moieties. Highlighted here is the recently discovered Sandmeyer trifluoromethylation approach, which now permits aromatic amines to be substrates in a direct trifluoromethylation strategy.

  三氟甲基化的一种手段：芳香族化合物三氟甲基化所赋予的有益性能继续推动新型试剂和反应的发现，以期在后期引入此类部分。这里重点介绍的是最近发现的Sandmeyer三氟甲基化方法，该方法现在允许芳香胺成为直接三氟甲基化策略的底物。
• 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.