potassium 4-chloro-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 4-chloro-2-nitrophenolate
• 英文别名: Potassium;4-chloro-2-nitrophenolate；potassium;4-chloro-2-nitrophenolate
• 化学式: C₆H₃ClNO₃*K
• 分子量: 211.646
• InChiKey: UVUAVYGUCZQNLJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.67
• 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：
  3

反应信息

• 作为反应物：
  描述：

  potassium 4-chloro-2-nitrophenolate 在 盐酸 、 tin(II) chloride dihdyrate 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 64.0h， 生成 [(2-{(2-[2-bis(methoxycarbonylmethyl)amino-4-chlorophenoxy]oct-7-en-2-yl)oxy}-4-formylphenyl)(methoxycarbonylmethyl)amino]acetic acid methyl ester
  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
• 作为产物：
  描述：

  4-氯-2-硝基苯酚 在 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以98%的产率得到potassium 4-chloro-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

• Elucidation of the Mechanism of Polysaccharide Cleavage by Chondroitin AC Lyase from <i>Flavobacterium </i><i>h</i><i>eparinum</i>
  作者：Carl S. Rye、Stephen G. Withers

  DOI：10.1021/ja020627c

  日期：2002.8.1

  enzyme has allowed the measurement of defined and reproducible k(cat) and K(m) values and has expanded the range of mechanistic studies that can be performed. The primary deuterium kinetic isotope effect upon k(cat)/K(m) for the abstraction of the proton alpha to the carboxylic acid was measured to be 1.67 +/- 0.07, showing that deprotonation occurs in a rate-limiting step. Using substrates with leaving

  来自肝素黄杆菌的软骨素 AC 裂解酶通过消除机制降解硫酸软骨素糖胺聚糖，产生在其非还原端具有 delta4,5-不饱和糖醛酸残基的二糖或寡糖。关于该酶促反应的键断裂和形成步骤的顺序的机制细节不存在，主要是由于聚合物底物的不均匀性质。为这种酶创建了一类新的合成底物，可以测量定义的和可重复的 k(cat) 和 K(m) 值，并扩大了可以进行的机械研究的范围。主要氘动力学同位素对 k(cat)/K(m) 的质子 α 提取到羧酸的影响测量为 1.67 +/- 0.07，表明去质子化发生在限速步骤中。使用具有不同反应性的离去基团的底物，产生了平坦的线性自由能关系，表明 C4-O4 键在速率决定步骤中没有断裂。综上所述，这些结果强烈暗示了一种逐步机制。与此一致的是二次氘动力学同位素对 4-[(2)H]-基板上的 1.01 +/- 0.03 的 k(cat)/K(m) 影响的测量，表明在C4 在限速步骤
• Kinetics and Mechanism of Nucleophilic Displacement Reactions of Y-Substituted Phenyl Benzoates with Cyanide Ion
  作者：Song-I Kim、Eun-Hee Kim、Ik-Hwan Um

  DOI：10.5012/bkcs.2010.31.03.689

  日期：2010.3.20

  Discussion The kinetic study was performed spectrophotometrically. All reactions proceeded with quantitative liberation of Y-substituted phenoxide ion (and/or its conjugate acid) under pseudo-first- order conditions (i.e., the nucleophile concentration in excess over the substrate concentration). The reactions obeyed first- order kinetics and pseudo-first-order rate constants (

  Y 取代苯甲酸苯酯 (1) 和苯硫代苯甲酸苯酯 (2) 与 CN 反应的二级速率常数汇总 - 在 80 mol % H 2 O/20 mol % DMSO 中，温度为 25.0 ± 0.1 o C a entry Y p K a 10 2 k CN- / M –1 s –1 12a 4-MeO 10.20 0.843 b 2.13 b 4-Me 10.19 0.783 b 1.89 c 3-CH 3 10.08 0.724 - d H 9.95 1.02 b 2.75 e 4-Cl 9.38 2.32 - f 3-COMe 9.19 3.59 b - g 3-Cl 9.02 4.19 - h 3-CHO 8.98 3.93 - i 4-COOEt 8.50 6.07 - j 3-NO 2 8.35 14.1 b 18.0 k 4-COMe 8.05 7.68 b 7.88 l 4-CN 7
• Ba-Saif, Salem A.; Maude, Antony B.; Williams, Andrew, Journal of the Chemical Society. Perkin transactions II, 1994, # 12, p. 2395 - 2400
  作者：Ba-Saif, Salem A.、Maude, Antony B.、Williams, Andrew

  DOI：——

  日期：——
• Synthesis and Characterization of a New Red-Emitting Ca²⁺ Indicator, Calcium Ruby
  作者：Stéphane Gaillard、Aleksey Yakovlev、Camilla Luccardini、Martin Oheim、Anne Feltz、Jean-Maurice Mallet

  DOI：10.1021/ol070648h

  日期：2007.7.1

  Calcium Ruby m-Cl (X = H, Y = Cl) is a visible-light excited red-emitting calcium concentration ([Ca2+]) indicator dye (579/598 nm peak excitation/emission) with a side arm for conjugation via EDC or click chemistry. Its large molar extinction and high quantum yield rank it among the brightest long-wavelength Ca2+ indicators. Calcium Ruby is a promising alternative to existing dyes for imaging [Ca2+] in multicolor fluorescence applications or in the presence of yellow-green cellular autofluorescence.
• Maude, Antony B.; Williams, Andrew, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1997, # 2, p. 179 - 183
  作者：Maude, Antony B.、Williams, Andrew

  DOI：——

  日期：——