9-[2-(Hydroxymethyl)phenyl]-6-prop-2-enoxyxanthen-3-one | 1268520-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-[2-(Hydroxymethyl)phenyl]-6-prop-2-enoxyxanthen-3-one
• 英文别名: 9-[2-(hydroxymethyl)phenyl]-6-prop-2-enoxyxanthen-3-one
• CAS: 1268520-55-3
• 化学式: C₂₃H₁₈O₄
• 分子量: 358.394
• InChiKey: ZEOYIDRSGKFNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-[2-(Hydroxymethyl)phenyl]-6-prop-2-enoxyxanthen-3-one 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以97%的产率得到9-[2-(hydroxymethyl)phenyl]-6-[(Z)-prop-1-enoxy]xanthen-3-one
  参考文献：
  名称：

  Development and Applications of Fluorogenic Probes for Mercury(II) Based on Vinyl Ether Oxymercuration

  摘要：

  Mercury is a major threat to the environment and to human health. It is highly desirable to develop a user-friendly kit for on-site mercury detection. Such a method must be able to detect mercury below the threshold levels for drinking water, 1-2 ppb. We developed a fluorescence method based on the oxymercuration of vinyl ethers to detect mercury in dental and environmental samples. Chloride ions interfered with the oxymercuration reaction, but the addition of AgNO3 solved this problem. Fine electronic and structural tuning led to the development of a more responsive probe that was less sensitive to chloride ion interference. This second-generation probe could detect 1 ppb mercury ions in water.

  DOI：

  10.1021/ja108028m
• 作为产物：
  描述：

  fluorescein free acid 在 二异丁基氢化铝 、 potassium carbonate 、 氯化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 9-[2-(Hydroxymethyl)phenyl]-6-prop-2-enoxyxanthen-3-one
  参考文献：
  名称：

  An activity-based fluorescent sensor with a penta-coordinate N-donor binding site detects Cu ions in living systems

  摘要：

  一种基于活性的新型传感器在 Cu2+ 离子存在时可使荧光增强 63 倍。该传感器仅在谷胱甘肽和环境中的氧气存在时通过一种可信的 CuII 氢过氧化物发挥作用。

  DOI：

  10.1039/d3cc02201c

文献信息

• Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-On Fluorescent Probe
  作者：Ho Yu Au-Yeung、Jefferson Chan、Teera Chantarojsiri、Christopher J. Chang

  DOI：10.1021/ja4072964

  日期：2013.10.9

  Iron is an essential metal for living organisms, but misregulation of its homeostasis at the cellular level can trigger detrimental oxidative and/or nitrosative stress and damage events. Motivated to help study the physiological and pathological consequences of biological iron regulation, we now report a reaction-based strategy for monitoring labile Fe2+ pools in aqueous solution and living cells. Iron Probe 1 (IP1) exploits a bioinspired, iron-mediated oxidative C-O bond cleavage reaction to achieve a selective turn-on response to Fe2+ over a range of cellular metal ions in their bioavailable forms. We show that this first-generation chemical tool for fluorescence Fe2+ detection can visualize changes in exchangeable iron stores in living cells upon iron supplementation or depletion, including labile iron pools at endogenous, basal levels. Moreover, IP1 can be used to identify reversible expansion of labile iron pools by stimulation with vitamin C or the iron regulatory hormone hepcidin, providing a starting point for further investigations of iron signaling and stress events in living systems as well as future probe development.
• FLUORESCENT CHEMODOSIMETERS FOR MERCURY IONS BASED ON THE OXYMERCURATION OF VINYL ETHERS
  申请人：Koide Kazunori

  公开号：US20120164740A1

  公开（公告）日：2012-06-28

  The present invention is a method to produce and to use a fluorogenic chemodosimeter for the detection of mercury ions in a sample at temperature ranges from about 0° C. to 100° C.
• Development and Applications of Fluorogenic Probes for Mercury(II) Based on Vinyl Ether Oxymercuration
  作者：Shin Ando、Kazunori Koide

  DOI：10.1021/ja108028m

  日期：2011.3.2

  Mercury is a major threat to the environment and to human health. It is highly desirable to develop a user-friendly kit for on-site mercury detection. Such a method must be able to detect mercury below the threshold levels for drinking water, 1-2 ppb. We developed a fluorescence method based on the oxymercuration of vinyl ethers to detect mercury in dental and environmental samples. Chloride ions interfered with the oxymercuration reaction, but the addition of AgNO3 solved this problem. Fine electronic and structural tuning led to the development of a more responsive probe that was less sensitive to chloride ion interference. This second-generation probe could detect 1 ppb mercury ions in water.
• An activity-based fluorescent sensor with a penta-coordinate N-donor binding site detects Cu ions in living systems
  作者：Kunika Gupta、Ankona Datta

  DOI：10.1039/d3cc02201c

  日期：——

  A novel activity-based sensor afforded 63 times fluorescence enhancement in the presence of Cu²⁺ ions. The sensor functioned only in the presence of glutathione and ambient oxygen via a plausible Cu^II hydroperoxo species.

  一种基于活性的新型传感器在 Cu2+ 离子存在时可使荧光增强 63 倍。该传感器仅在谷胱甘肽和环境中的氧气存在时通过一种可信的 CuII 氢过氧化物发挥作用。