potassium salt of 5-methyl-2-nitrophenol | 73630-14-5

• 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 salt of 5-methyl-2-nitrophenol
• 英文别名: potassium 5-methyl-2-nitrophenoxide；Potassium;5-methyl-2-nitrophenolate；potassium;5-methyl-2-nitrophenolate
• CAS: 73630-14-5
• 化学式: C₇H₆NO₃*K
• 分子量: 191.228
• InChiKey: QWJXIMPUMBINAE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.02
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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 salt of 5-methyl-2-nitrophenol 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium ethanolate 、 1,8-双二甲氨基萘 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.42h， 生成 1-<2-<2-ethoxycarbonylethyl(ethoxycarbonylmethyl)amino>-4-hydroxyphenoxy>-2-<2-bis(ethoxycarbonylmethyl)amino-5-methylphenoxy>ethane
  参考文献：
  名称：

  Smith, Gerry A.; Metcalfe, James C.; Clarke, Sonia D., Journal of the Chemical Society. Perkin transactions II, 1993, # 6, p. 1195 - 1204

  摘要：

  DOI：
• 作为产物：
  描述：

  6-硝基间甲酚 在 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以92%的产率得到potassium salt of 5-methyl-2-nitrophenol
  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
• 作为试剂：
  描述：

  6-硝基间甲酚 、 氧化环己烯 在 potassium salt of 5-methyl-2-nitrophenol 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以56%的产率得到(1R,2S)-2-(5-甲基-2-硝基苯氧基)环己烷-1-醇
  参考文献：
  名称：

  Biologically useful chelators that release Ca2+ upon illumination

  摘要：

  DOI：

  10.1021/ja00218a034

文献信息

• Chelators whose affinity for calcium is decreased by illumination
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0177202A1

  公开（公告）日：1986-04-09

  Calcium chelating compounds having a decreased affinity for calcium following illumination and of the formulae or wherein: A is -NO2 or -H; R' is -H (unless R2 is H), -CH3 or other alkyl, -F, -Cl or -Br; R2 is -H (unless R' is H), -CH3 or other alkyl, -F, -Cl, -Br, or C1-C4 alkoxy; R3. R4 and R5 are independently -H, OH, NR6R7, or alkoxy, or R3 and R4 together are -OCH20- or -OCH2CH20- and R5 is -H, OH, NR6R7, or alkoxy, or R4 and R5 together are -OCH2O- or OCH2CH2O- and R3 is -H, OH, NR6R7, or alkoxy; X is -OH, alkoxy, -Cl, -Br, -NR6R7, -OCOCH3, -OCOCF3, -OCOCH2NH2, -OP03H, or -OS02CH3; R6 and R7 are independently -H, methyl or ethyl; D is O, N, NH, or N alkyl; Q is a double bond when D is N and a single bond otherwise; R8 is H and R9 is H or R8 and R9, together with heteroatom D, the carbon adjacent R8, and the phenyl ring adjacent to R9, form a quinoline ring system (D=N, Q=double bond); and W is -H, -OH, alkoxy or -NHR6, the compound optionally being as a physiologically acceptable salt or ester thereof.

  光照后对钙的亲和力降低的钙螯合化合物，其式为 或 其中 A 是-NO2 或-H； R'是-H（除非 R2 是 H）、-CH3 或其他烷基、-F、-Cl 或-Br； R2 是-H（除非 R' 是 H）、-CH3 或其他烷基、-F、-Cl、-Br 或 C1-C4 烷氧基； R3.R4 和 R5 独立地为-H、OH、NR6R7 或烷氧基，或 R3 和 R4 同为-OCH20-或-OCH2CH20-，R5 为-H、OH、NR6R7 或烷氧基，或 R4 和 R5 同为-OCH2O- 或 OCH2CH2O-，R3 为-H、OH、NR6R7 或烷氧基； X 是-OH、烷氧基、-Cl、-Br、-NR6R7、-OCOCH3、-OCOCF3、-OCOCH2NH2、-OP03H 或 -OS02CH3； R6 和 R7 独立地为-H、甲基或乙基； D 是 O、N、NH 或 N烷基； 当 D 为 N 时，Q 为双键，否则为单键； R8 是 H，R9 是 H 或 R8 和 R9 与杂原子 D、与 R8 相邻的碳和与 R9 相邻的苯环一起形成一个喹啉环系统（D=N，Q=双键）；以及 W 是-H、-OH、烷氧基或-NHR6，化合物可选为生理上可接受的盐或酯。
• New photosensitive calcium chelators
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0292161A2

  公开（公告）日：1988-11-23

  The present invention discloses a new class of calcium chelating compounds which have a decreased affinity for calcium following illumination. These new compounds contain a photolabile nitrobenzyl derivative coupled to a tetracarboxylate Ca²⁺ chelating parent compound having the octacoordinate chelating groups characteristic of EGTA or BAPTA. However unlike EGTA or BAPTA-like compounds, in which the two halves of the chelator are linked by a simple 1,2-ethanediyl moiety, the compounds of the present invention modify the stereochemical conformation of this linkage by adding bulky substituents or incorporating the linkage into a carbocyclic or heterocyclic ring. In a first form, the new compounds are comprised of a BAPTA-like chelator coupled to a single 2-nitrobenzyl derivative, which in turn is a photochemical precursor of a 2-nitrosobenzophenone. In a second form, the new compounds are comprised of a BAPTA-like chelator coupled to two 2-nitrobenzyl derivatives, themselves photochemical precursors of the related 2-nitrosobenzophenones.

  本发明公开了一类新的钙螯合化合物，该化合物在光照下对钙的亲和力降低。这些新化合物含有一种可光化的硝基苄基衍生物，该衍生物与具有 EGTA 或 BAPTA 所特有的八配位螯合基团的四羧酸 Ca²⁺ 螯合母体化合物偶联。然而，与 EGTA 或 BAPTA 类化合物不同的是，本发明的化合物通过简单的 1,2-乙二基分子连接螯合剂的两半部分，通过添加笨重的取代基或将连接部分并入碳环或杂环来改变这种连接的立体化学构象。在第一种形式中，新化合物由类似 BAPTA 的螯合剂与单一 2-硝基苯基衍生物耦合而成，而后者又是 2-亚硝基二苯甲酮的光化学前体。在第二种形式中，新化合物由一种 BAPTA 类螯合剂和两种 2-硝基苯基衍生物组成，这两种衍生物本身就是相关 2-亚硝基二苯甲酮的光化学前体。
• Fluorescent indicator dyes for calcium working at long wavelengths
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0314480A2

  公开（公告）日：1989-05-03

  A new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths combine at least one tricyclic chromophore with a tetracarboxylate parent CA2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA2+] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.

  一类具有可见激发和发射波长的新型钙特异性荧光指示剂染料将至少一种三环发色团与四羧酸母体 CA2+ 螯合化合物结合在一起，该化合物具有 BAPTA 特有的八配位配位基团模式，从而产生类似罗丹明或荧光素的荧光团。钙2+的结合可使新化合物的荧光增加 40 倍。钙2+的解离常数在 0.37-2.3 微摩尔范围内，因此新指示剂对高浓度[CA2+]的分辨能力比以前的前代化合物（如 quin-2 或 fluo-2）更强。与以前的指示剂所需的紫外波长相比，新化合物的可见光激发波长更便于荧光显微镜和流式细胞仪的使用。
• 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.
• TSIEN, ROGER Y.;GRYNKIEWICZ, GRZEGORZ;MINTA, AKWASI
  作者：TSIEN, ROGER Y.、GRYNKIEWICZ, GRZEGORZ、MINTA, AKWASI

  DOI：——

  日期：——