potassium-5-fluoro-2-nitrophenolate

• 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: potassium-5-fluoro-2-nitrophenolate
• 英文别名: potassium salt of 5-fluoro-2-nitrophenol；potassium 5-fluoro-2-nitrophenol；Potassium;5-fluoro-2-nitrophenolate；potassium;5-fluoro-2-nitrophenolate
• 化学式: C₆H₃FNO₃*K
• 分子量: 195.191
• InChiKey: FWRSJNYVYQPNHB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.19
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium-5-fluoro-2-nitrophenolate 在 palladium on activated charcoal 吡啶 、 水 、 氢气 、 diborane(6) 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.67h， 生成 8,29-Difluoro-2,5,15,22-tetraoxa-12,25-diazatetracyclo[24.4.0.06,11.016,21]triaconta-1(26),6(11),7,9,16(21),17,19,27,29-nonaen-18-amine
  参考文献：
  名称：

  Smith, Gerry A.; Kirschenlohr, Heide L.; Metcalfe, James C., Journal of the Chemical Society. Perkin transactions II, 1993, # 6, p. 1205 - 1210

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氟-2-硝基苯酚 在 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以95%的产率得到potassium-5-fluoro-2-nitrophenolate
  参考文献：
  名称：

  Calcium Rubies: A Family of Red-Emitting Functionalizable Indicators Suitable for Two-Photon Ca²⁺ Imaging

  摘要：

  We designed Calcium Rubies, a family of functionalizable BAPTA-based red-fluorescent calcium (Ca2+) indicators as new tools for biological Ca2+ imaging. The specificity of this Ca2+-indicator family is its side arm, attached on the ethylene glycol bridge that allows coupling the indicator to various groups while leaving open the possibility of aromatic substitutions on the BAPTA core for tuning the Ca2+-binding affinity. Using this possibility we now synthesize and characterize three different CaRubies with affinities between 3 and 22 mu M. Their long excitation and emission wavelengths (peaks at 586/604 nm) allow their use in otherwise challenging multicolor experiments, e.g., when combining Ca2+ uncaging or optogenetic stimulation with Ca2+ imaging in cells expressing fluorescent proteins. We illustrate this capacity by the detection of Ca2+ transients evoked by blue light in cultured astrocytes expressing CatCh, a light-sensitive Ca2+-translocating channelrhodopsin linked to yellow fluorescent protein. Using time-correlated single-photon counting, we measured fluorescence lifetimes for all CaRubies and demonstrate a 10-fold increase in the average lifetime upon Ca2+ chelation. Since only the fluorescence quantum yield but not the absorbance of the CaRubies is Ca2+-dependent, calibrated two-photon fluorescence excitation measurements of absolute Ca2+ concentrations are feasible.

  DOI：

  10.1021/ja304018d

文献信息

• 一种2-（5-氟-2-硝基苯氧基）乙酸酯类化合物的合成方法
  申请人：利尔化学股份有限公司

  公开号：CN113045424A

  公开（公告）日：2021-06-29

  本发明涉及农药化工领域，更具体地讲一种2‑(5‑氟‑2‑硝基苯氧基)乙酸酯类化合物的合成方法，所述方法是使式(I)化合物和式(II)化合物在催化剂作用下进行反应得目标产物；所述催化剂为碘化钠、碘化钾中的至少一种；其中，R1为钠或钾；R2为C1‑C6烷基或苄基。该合成工艺对反应后产生的副产物氯化钾，该方法可经过简单过滤可有效分离，从而对其实现资源化利用。另外通过蒸除溶剂的手段可实现溶剂的循环利用，极大减少资源浪费，节约成本，保护环境。
• Analogs of the cyclic hydroxamic acid 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one (DIMBOA): decomposition to benzoxazolinones and reaction with .beta.-mercaptoethanol
  作者：Jeffrey Atkinson、Peter Morand、John T. Arnason、Hermann M. Niemeyer、Hector R. Bravo

  DOI：10.1021/jo00005a025

  日期：1991.3

  Analogues of the aglucones of naturally occurring cyclic hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-ones) from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the ring-substituted methyl alpha-(o-nitrophenoxy)-alpha-methoxyacetates, followed by demethylation of the C-2 methoxy group with BBr3 or BCl3 to reveal the 2-hydroxy group. A structure-activity series was produced by varying the substituent at C-7 on the aromatic ring [R = MeO (1), t-Bu (6), Me (7), H (8), Cl (9), F (10), CO2Me (11a)]. The pK(a) values for the hydroxamic acid and the phenol moieties were determined for each member of the C-7 series. They correlated well with sigma in a linear free energy relationship (LFER) yielding values of rho = 0.71 (with sigma-p) for pK(a1) (the hydroxamic acid) and rho = 1.6 (with sigma-m) for pK(a2) (the phenol). A LFER also existed between the rate constants for the unimolecular decomposition of these hydroxamic acids to benzoxazolinones and sigma+ (rho = 1.1). The rates of hydroxamic acid reduction to lactams by beta-mercaptoethanol were also investigated. It was found that only compounds with electron-rich aromatic rings and specifically an oxa functionality para to the hydroxamic acid nitrogen atom (compounds 1 and 3-5) had measurable rates of reduction. H-1 NMR spectra recorded during this reaction in D2O buffers (pD9), however, showed that compounds 1, 2, 6-9 (the only ones investigated) formed a hemithioacetal at C-2 even though only 1 has a measurable rate of reduction by the same thiol. The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic nitrogen of a resonance-stabilized ion pair.
• Calcium Rubies: A Family of Red-Emitting Functionalizable Indicators Suitable for Two-Photon Ca²⁺ Imaging
  作者：Mayeul Collot、Christina Loukou、Aleksey V. Yakovlev、Christian D. Wilms、Dongdong Li、Alexis Evrard、Alsu Zamaleeva、Laurent Bourdieu、Jean-François Léger、Nicole Ropert、Jens Eilers、Martin Oheim、Anne Feltz、Jean-Maurice Mallet

  DOI：10.1021/ja304018d

  日期：2012.9.12

  We designed Calcium Rubies, a family of functionalizable BAPTA-based red-fluorescent calcium (Ca2+) indicators as new tools for biological Ca2+ imaging. The specificity of this Ca2+-indicator family is its side arm, attached on the ethylene glycol bridge that allows coupling the indicator to various groups while leaving open the possibility of aromatic substitutions on the BAPTA core for tuning the Ca2+-binding affinity. Using this possibility we now synthesize and characterize three different CaRubies with affinities between 3 and 22 mu M. Their long excitation and emission wavelengths (peaks at 586/604 nm) allow their use in otherwise challenging multicolor experiments, e.g., when combining Ca2+ uncaging or optogenetic stimulation with Ca2+ imaging in cells expressing fluorescent proteins. We illustrate this capacity by the detection of Ca2+ transients evoked by blue light in cultured astrocytes expressing CatCh, a light-sensitive Ca2+-translocating channelrhodopsin linked to yellow fluorescent protein. Using time-correlated single-photon counting, we measured fluorescence lifetimes for all CaRubies and demonstrate a 10-fold increase in the average lifetime upon Ca2+ chelation. Since only the fluorescence quantum yield but not the absorbance of the CaRubies is Ca2+-dependent, calibrated two-photon fluorescence excitation measurements of absolute Ca2+ concentrations are feasible.
• Smith, Gerry A.; Kirschenlohr, Heide L.; Metcalfe, James C., Journal of the Chemical Society. Perkin transactions II, 1993, # 6, p. 1205 - 1210
  作者：Smith, Gerry A.、Kirschenlohr, Heide L.、Metcalfe, James C.、Clarke, Sonia D.

  DOI：——

  日期：——