4-acetamido-5-nitrophthalic acid | 209324-71-0

• 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: 4-acetamido-5-nitrophthalic acid
• 英文别名: 4-acetylamino-5-nitro-phthalic acid；4-Acetylamino-5-nitro-phthalsaeure
• CAS: 209324-71-0
• 化学式: C₁₀H₈N₂O₇
• 分子量: 268.183
• InChiKey: QNBUCMNQOCMKOU-UHFFFAOYSA-N

物化性质

• 沸点：
  586.5±50.0 °C(Predicted)
• 密度：
  1.682±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-acetamido-5-nitrophthalic acid 在 硫酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 dimethyl 4,5-diaminophthalate
  参考文献：
  名称：

  SalenZn-bridged D-π-A Dyes For Dye-Sensitized Solar Cells

  摘要：

  AbstractA series of SalenZn based dyes with triphenylamine derivatives as the donor, benzoic acid as the acceptor, and coplanar Salen complexes as the spacer have been designed and synthesized for dye‐sensitized solar cells. The absorption, electrochemical, and photovoltaic properties for all sensitizers have been systematically investigated. When the tail length of the alkyl substituents is increased from C‐0 to C‐8 on the donor part, the efficiency of its DSSC augments evidently. It is found that the incorporation of bis‐carboxyl groups instead of the single carboxyl group as anchoring groups induces a remarkable enhancement of the electron injection efficiency from the excited dyes to the TiO2 semiconductor and generates higher electron density and voltage.

  DOI：

  10.1002/cjoc.201300924
• 作为产物：
  描述：

  4’,5’-二甲基-2’-硝基乙酰苯胺 在 potassium permanganate 、 硫酸 作用下， 以 水 为溶剂， 以59%的产率得到4-acetamido-5-nitrophthalic acid
  参考文献：
  名称：

  Development of a Fluorescent Indicator for Nitric Oxide Based on the Fluorescein Chromophore.

  摘要：

  内源性一氧化氮（NO）似乎可以调节许多生理和病理生理过程。为了获得一氧化氮在体内功能的直接证据，我们开发了 4，5-二氨基荧光素（DAF-2）作为一氧化氮的新型荧光指示剂。由 NO 和 DAF-2 反应生成的绿色荧光三唑荧光素对 NO 具有高灵敏度（检测限：5 nM）。将膜渗透性 DAF-2 二乙酸酯（DAF-2DA）装入活化的大鼠主动脉平滑肌细胞中，细胞内的酯键被酯酶水解，生成 DAF-2。细胞内的荧光增加与 NO 浓度有关。这种成像方法可用于在分子水平上研究 NO 的动态生物作用，并具有较高的时间和空间分辨率。

  DOI：

  10.1248/cpb.46.373

文献信息

• Sur l'acide dinitro-4,5-phtalique
  作者：Henri Goldstein、Jean-Pierre Merminod

  DOI：10.1002/hlca.19520350506

  日期：1952.8.1

  L'oxydation de l'acide dinitro-4,5-méthyl-2-benzoïque et celle du dinitro-4,5-xylène-1,2 conduisent à l'acide dinitro-4,5-phtalique; ce composé possède un groupe nitro mobile, qui se laisse remplacer facilement par d'autres substituants sous l'action de réactifs nucléophiles.

  酰化二硝基-4,​​5-二甲基-2-苯并呋喃二氧基化的二硝基-4,​​5-二甲苯-1,2-亚胺二硝基-4,​​5-邻苯二酚; 硝基流动性组合物，快速替代品，亲核性亲和力替代品。
• Effect of regioisomeric substitution patterns on the performance of quinoxaline-based dye-sensitized solar cells
  作者：Jong Min Park、Chang Young Jung、Yue Wang、Hyun Dong Choi、Seong Je Park、Pinyin Ou、Woo-Dong Jang、Jae Yun Jaung

  DOI：10.1016/j.electacta.2018.12.133

  日期：2019.3

  dyes (NQXs) were synthesized to study the effect of substitution patterns on the performance of quinoxaline-based dye sensitized solar cells (DSSCs). The 1H NMR results indicated that the substitution patterns of ethylene groups on the quinoxaline unit greatly affect the molecular architecture through CH⋯N hydrogen bonding, which also influenced the absorption and efficiency of the DSSCs. The highest

  合成了基于区域异构体的喹喔啉类染料（NQX s），以研究取代模式对基于喹喔啉类染料敏化太阳能电池（DSSC）性能的影响。的1个1 H NMR结果表明，喹喔啉单元上乙烯基团的取代模式极大地影响到C的分子结构ħ⋯Ñ氢键，这也影响了DSSC中的吸收和效率。通过循环伏安法和可见吸收研究，NQX的最高占据分子轨道（HOMO）水平估计为0.94至0.99 V，这适用于DSSC。NQX的光电流密度-电压曲线和入射光电子转换效率谱s表明，在喹喔啉的2-和3-位上引入吩噻嗪基是DSSC中基于喹喔啉的有机敏化剂最有效的模式。
• Detection and Imaging of Nitric Oxide with Novel Fluorescent Indicators:  Diaminofluoresceins
  作者：Hirotatsu Kojima、Naoki Nakatsubo、Kazuya Kikuchi、Shigenori Kawahara、Yutaka Kirino、Hiroshi Nagoshi、Yasunobu Hirata、Tetsuo Nagano

  DOI：10.1021/ac9801723

  日期：1998.7.1

  Nitric oxide is a gaseous, free radical which plays a role as an intracellular second messenger and a diffusable intercellular messenger. To obtain direct evidence for NO functions in vivo, we have designed and synthesized diaminofluoresceins (DAFs) as novel fluorescent indicators for NO. The fluorescent chemical transformation of DAFs is based on the reactivity of the aromatic vicinal diamines with NO in the presence of dioxygen. The N-nitrosation of DAFs, yielding the highly green-fluorescent triazole form, offers the advantages of specificity, sensitivity, and a simple protocol for the direct detection of NO (detection limit 5 nM). The fluorescence quantum efficiencies are increased more than 100 times after the transformation of DAFs by NO. Fluorescence detection with visible light excitation and high sensitivity enabled the practical assay of NO production in living cells. Membrane-permeable DAF-2 diacetate (DAF-2 DA) can be used for real-time bioimaging of NO with fine temporal and spatial resolution. The dye was loaded into activated rat aortic smooth muscle cells, where the ester bonds are hydrolyzed by intracellular esterase, generating DAF-2. The fluorescence in the cells increased in a NO concentration-dependent manner.

  一氧化氮是一种气态自由基，它既是细胞内的第二信使，也是可扩散的细胞间信使。为了直接证明一氧化氮在体内的功能，我们设计并合成了二氨基荧光素（DAFs），作为一氧化氮的新型荧光指示剂。DAFs 的荧光化学变化是基于芳香族环状二胺在二氧存在下与 NO 的反应性。DAFs 的 N-亚硝基化反应生成了高绿色荧光的三唑形式，具有特异性、灵敏度高、操作简单等优点，可直接检测 NO（检测限为 5 nM）。DAF 被 NO 转化后，荧光量子效率提高了 100 多倍。利用可见光激发的荧光检测和高灵敏度，可以对活细胞中的 NO 生成进行实际检测。膜渗透性 DAF-2 diacetate（DAF-2 DA）可用于对 NO 进行实时生物成像，并具有较高的时间和空间分辨率。将染料装入活化的大鼠主动脉平滑肌细胞，细胞内酯酶水解酯键，生成 DAF-2。细胞内的荧光增加与 NO 浓度有关。
• Synthesis of new di-anchoring organic sensitizer based on quinoxaline acceptor for dye-sensitized solar cells
  作者：Jong Min Park、Chang Young Jung、Joong Hyun Cho、Dae Hyun Kim、Yue Wang、Jae Yun Jaung

  DOI：10.1016/j.tetlet.2018.07.049

  日期：2018.8

  New quinoxaline-based organic sensitizer bearing di-anchoring group for dye-sensitized solar cells (DSSCs) was synthesized from diethyl 4,5-diaminophthaltate, in which was prepared under mild condition by using Takehito’s method. The synthesized sensitizer was compared with mono-anchoring sensitizer through absorption spectra, emission spectra, J-V curve, and IPCE spectra, indicating the di-anchoring

  由4,5-二氨基邻苯二甲酸二乙酯在温和条件下采用Takehito法制备了一种新型的染料敏化太阳能电池（DSSCs）的带有双锚定基团的喹喔啉类有机增敏剂。通过吸收光谱，发射光谱，J - V曲线和IPCE光谱将合成的敏化剂与单锚定敏化剂进行了比较，表明由于分子内电荷转移和通道效率更高，双锚定基团显着提高了J sc值。数字增量。
• Development of a Fluorescent Indicator for Nitric Oxide Based on the Fluorescein Chromophore.
  作者：Hirotatsu KOJIMA、Kuniko SAKURAI、Kazuya KIKUCHI、Shigenori KAWAHARA、Yutaka KIRINO、Hiroshi NAGOSHI、Yasunobu HIRATA、Tetsuo NAGANO

  DOI：10.1248/cpb.46.373

  日期：——

  Endogenous nitric oxide (NO) appears to modulate many physiological and pathophysiolgoical processes. In order to obtain direct evidence for NO functions in vivo, we have developed 4, 5-diaminofluorescein (DAF-2) as a novel fluorescent indicator for NO. Green-fluorescent triazolofluorescein formed by the reaction of NO and DAF-2 affords high sensitivity for NO (detection limit : 5 nM). Membrane-permeable DAF-2 diacetate (DAF-2DA) was loaded into activated rat aortic smooth muscle cells, where the ester bonds are hydrolyzed by intracellular esterase, generating DAF-2. The fluorescence in the cells increased in a NO concentration-dependent manner. This imaging method should be useful for studies of the dynamic biological actions of NO at the molecular level with fine temporal and spatial resolution.

  内源性一氧化氮（NO）似乎可以调节许多生理和病理生理过程。为了获得一氧化氮在体内功能的直接证据，我们开发了 4，5-二氨基荧光素（DAF-2）作为一氧化氮的新型荧光指示剂。由 NO 和 DAF-2 反应生成的绿色荧光三唑荧光素对 NO 具有高灵敏度（检测限：5 nM）。将膜渗透性 DAF-2 二乙酸酯（DAF-2DA）装入活化的大鼠主动脉平滑肌细胞中，细胞内的酯键被酯酶水解，生成 DAF-2。细胞内的荧光增加与 NO 浓度有关。这种成像方法可用于在分子水平上研究 NO 的动态生物作用，并具有较高的时间和空间分辨率。