1-hydroxy-2-(prop-2'-enyl)-9,10-anthraquinone | 64302-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-2-(prop-2'-enyl)-9,10-anthraquinone
• 英文别名: 1-hydroxy-2-(prop-2'-enyl)anthraquinone；2-allyl-1-hydroxyanthracene-9,10-dione；2-allyl-1-hydroxy-9,10-anthraquinone；2-allyl-1-hydroxyanthra-9,10-quinone；R162；2-Allyl-1-hydroxyanthrachinon；1-hydroxy-2-prop-2-enylanthracene-9,10-dione
• CAS: 64302-87-0
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: IMUBGIOLZQTIGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxy-2-(prop-2'-enyl)-9,10-anthraquinone 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-((E)-3-Hydroxy-oct-1-enyl)-11b-methoxy-4-propyl-11bH-1,3-dioxa-benzo[de]anthracen-7-one
  参考文献：
  名称：

  Caged trans-4-Hydroxy-2-nonenal

  摘要：

  (GRAPHICS)A caged 4-hydroxy-2-nonenal (4-HNE) has been prepared and its photochemistry investigated. Upon photolysis, 1 releases 4-HNE in up to 100% yield. From these photolyses, 4-HNE could be isolated in up to 91% yield. 4-HNE is produced under either aerobic or anaerobic conditions. The caging strategy does not require prior preparation of 4-HNE and, therefore, represents a three-step synthetic route to the bioactive enal in 48% overall yield.

  DOI：

  10.1021/ol048478l
• 作为产物：
  描述：

  1-羟基蒽醌 在 铁粉 、 potassium carbonate 、 1-methylimidazolium tetrafluoroborate 、 1-苄基-3-甲基咪唑氯盐 作用下， 以 丙酮 为溶剂， 反应 0.13h， 生成 1-hydroxy-2-(prop-2'-enyl)-9,10-anthraquinone
  参考文献：
  名称：

  Efficient reductive Claisen rearrangement of prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones with iron powder in ionic liquids

  摘要：

  本研究介绍了铁介导的各种丙-2'-烯氧基蒽醌和 2'-氯丙-2'-烯氧基蒽醌到 1-羟基-2-(丙-2'-烯基)蒽醌和蒽呋喃酮的快速和选择性还原性克莱森重排反应。 所有反应均在离子液体[Bzmim]Cl（1-苄基-3-甲基咪唑氯化物）和[Hmim]BF$_{4}$（1-甲基咪唑四氟硼酸盐）的混合物中进行，反应时间短（5-35 分钟）。我们的研究表明，1-(丙-2'-烯氧基)蒽醌比 1-(2'-氯丙-2'-烯氧基)蒽醌在进行这种重排反应时更为活跃。

  DOI：

  10.3906/kim-1711-49

文献信息

• Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal
  作者：Paul B. Jones、Robert G. Brinson、Saurav J. Sarma、Salwa Elkazaz

  DOI：10.1039/b810954k

  日期：——

  anthraquinonyl chromophore to achieve water solubility, we studied the photochemistry of various substituents to understand their effect on the photochemistry. We observed a significant heavy atom effect that severely reduced the rate of oxidative cleavage of the alkoxy group. Based on the results of our substituent study, we designed a new caged 4-HNE that is soluble under physiological conditions, and

  在我们研究1-烷氧基-9,10-蒽醌的光化学过程中，我们开发了第二代笼状的4-羟基-反式-2-壬烯醛（4-HNE）。当我们优化蒽醌基生色团以达到水溶性时，我们研究了各种取代基的光化学，以了解它们对光化学的影响。我们观察到了显着的重原子效应，该效应严重降低了烷氧基的氧化裂解速率。根据我们对取代基的研究结果，我们设计了一种新的笼状4-HNE，该笼在生理条件下可溶，并且可以高产率光化学释放4-HNE。
• Photocaged dicarbonyl probe provides spatiotemporal control over protein glycation
  作者：Alexander K. Hurben、Peng Ge、Jacob L. Bouchard、Todd M. Doran、Natalia Y. Tretyakova

  DOI：10.1039/d1cc06651j

  日期：——

  On demand dicarbonyl-protein adduct formation in live cells is achieved with subcellular specificity by a targetable, light triggered probe.

  通过可定位的、光触发的探针，在活细胞中实现了亚细胞特异性的需求二羰基蛋白加合物形成。
• Reductive claisen rearrangements of anthraquinone allyl ethers
  作者：Ian K. Boddy、J. Boniface、Richard C. Cambie、Peter A. Craw、David S. Larsen、Hamish McDonald、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1016/s0040-4039(00)85614-2

  日期：1982.1

  Gentle heating of allyloxyanthraquinones with sodium dithionite in dimethylformanide - water effects a rapid and controlled rearrangement to give high yields of 2-allyanthraquinones.

  将二甲基甲酰胺-水中的连二亚硫酸钠与烯丙氧基蒽醌温和加热，可快速而受控地进行重排，从而获得高产率的2-烯丙基蒽醌。
• ELECTROCHEMICAL SENSORS
  申请人：KAHN Carolyn R.

  公开号：US20120187000A1

  公开（公告）日：2012-07-26

  Systems and methods are provided for detecting the presence of an analyte in a sample. A solid state electrochemical sensor can include a redox active moiety having an oxidation and/or reduction potential that is sensitive to the presence of an analyte immobilized over a surface of a working electrode. A redox active moiety having an oxidation and/or reduction potential that is insensitive to the presence of the analyte can be used for reference. Voltammetric measurements made using such systems can accurately determine the presence and/or concentration of the analyte in the sample. The solid state electrochemical sensor can be robust and not require calibration or re-calibration.

  提供了用于检测样品中分析物存在的系统和方法。固态电化学传感器可以包括一个氧化还原活性基团，其氧化和/或还原电位对固定在工作电极表面的分析物的存在敏感。可以使用一个对分析物存在不敏感的氧化还原活性基团作为参考。使用这种系统进行伏安测量可以准确地确定样品中分析物的存在和/或浓度。固态电化学传感器可以坚固耐用，不需要校准或重新校准。
• Real-time imaging method of NAPDH-dependent metabolic activity in cell and use thereof
  申请人：INDUSTRY FOUNDATION OF CHONNAM NATIONAL UNIVERSITY

  公开号：US10308973B1

  公开（公告）日：2019-06-04

  Provided is a real-time imaging method of NAPDH-dependent metabolic activity in a cell and a use thereof, and more particularly, an imaging method capable of measuring concentration gradient and change in an intracellular coenzyme using a mutant of metagenome-derived blue fluorescent protein (mBFP) in real-time and an application method thereof. In particular, the method of imaging and quantifying the coenzyme contained in various biological samples may be performed by improving fluorescence in a short time even under anaerobic conditions, without adding a substrate required for coenzyme measurement or conversion without destroying cells, and without consuming the time required for formation of a special structure (fluorophore) for generating fluorescence unlike the existing quantitative systems. In particular, provided is a stable quantitative/imaging technique that is directly applicable to biological samples having various complex compositions without signal interference caused by impurities by removing an inherent enzymatic activity of mBFP.

  本发明提供了一种细胞内 NAPDH 依赖性代谢活动的实时成像方法及其用途，更具体地说，是一种能够利用元基因组衍生的蓝色荧光蛋白（mBFP）突变体实时测量细胞内辅酶的浓度梯度和变化的成像方法及其应用方法。特别是，与现有的定量系统不同，该方法可以通过在短时间内提高荧光来成像和定量各种生物样本中含有的辅酶，即使在厌氧条件下也是如此，无需添加辅酶测量或转换所需的底物，无需破坏细胞，也无需消耗用于产生荧光的特殊结构（荧光团）的形成所需的时间。特别是，通过去除 mBFP 固有的酶活性，提供了一种稳定的定量/成像技术，可直接用于具有各种复杂成分的生物样品，而不会受到杂质造成的信号干扰。