2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione | 3319-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione
• 英文别名: 2-methyl-1,4,4a,9a-tetrahydro-anthraquinone；9.10-Dioxo-2-methyl-1.4.9.10.11.12-hexahydro-anthracen；2-Methyl-1,4,4a,9a-tetrahydro-anthrachinon；2-Methyl-1,4,4a,9a-tetrahydro-9,10-anthracenedione
• CAS: 3319-24-2
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: HMPTXYUENQEIPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione 在 N-溴代丁二酰亚胺(NBS) 、 copper(ll) sulfate pentahydrate 、 氨 、 三氟乙酸 、 potassium hydroxide 、 锌 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 生成 9,10-二溴-2-甲基蒽
  参考文献：
  名称：

  Synthesis and characterization of highly soluble blue emitting poly(2-vinylanthracene) with 9,10-di(2-naphthalenyl) and 9,10-di(3-quinolinyl) substituents

  摘要：

  Two new blue fluorescent polymers, poly(9,10-di(2-naphthalenyl)-2-vinylanthracene) (P(2ADN)) and poly(9,10-di(3-quinolinyl)-2-vinylanthracene) (P(3ADQ)), were polymerized from free radical solution addition polymerization with M-n = 21,500 and 15,400, respectively. The polymers are highly soluble in common organic solvents while P(3ADQ) is also soluble in polar solvents including a 1/1 mixture of ethanol/water. Both polymers are amorphous with excellent thermal stability (T-g (Midpoint) = 343 degrees C and 298 degrees C for P(2ADN) and P(3ADQ), respectively). P(2ADN) exhibited three prominent absorption bands in tetrahydrofuran (364, 383 and 403 nm) and is similar to that of P(3ADQ) (369, 384 and 404 nm). The solid-state Commission Internationale d'Eclairage (CIEx,y) color coordinates for illumination were (0.15, 0.10) for P(2ADN) and (0.15, 0.13) for P(3ADQ) which lied within the requirements for a true blue display color. The photoluminescence (PL) of the polymers red-shifted 16-17 nm from their respective pendant chromophore 2-methyl-9,10-di(2-naphthalenyl)anthracene (2MADN) and 2-methyl-9,10-di(3-quinolinyl)anthracene (3MADQ) and can be attributed to partial pi-pi stacking between the adjacent aromatic pendant groups in the polymer chains. The luminescences of 3MADQ and P(3ADQ) are sensitive to pH and the pK(a), for the alkalescent 3MADQ and P(3ADQ) calculated was 2.4 and 2.7, respectively. Both polymers have similar band-gap energy (E-g) between 2.88 and 2.91 eV, while the LUMO/HOMO for P(3ADQ) is shifted slightly downward -0.06 to -0.03 eV compared to P(2ADN). The mobility (mu(hole)) of the two polymers were measured to be 4.0 x 10(-7) and 10(-8) cm(2)/(V-s) for P(2ADN) and P(3ADQ), respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.04.021
• 作为产物：
  描述：

  1,4-萘醌 、 天然橡胶 在 1-(triethylsilyl)pyridin-1-ium-2,3,4,5,6-d5 trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione
  参考文献：
  名称：

  甲硅烷基三氟甲磺酸酯的路易斯酸度与催化狄尔斯-阿尔德反应的反应速率的相关性

  摘要：

  各种甲硅烷基三氟甲磺酸酯的路易斯酸度通过使用 [D5] 吡啶作为 2H NMR 光谱探针进行量化。报道了吡啶-甲硅烷基加合物的 2 H NMR 信号的化学位移。三氟甲磺酸甲硅烷酯催化的 Diels-Alder 反应的速率常数是通过使用 UV/Vis 光谱确定的。观察到 2H NMR 化学位移的幅度与所研究的大多数甲硅烷基三氟甲磺酸酯的速率常数的相关性，但 Me3SiOTf 表现出惊人的大偏差。对照实验表明可以排除狄尔斯-阿尔德反应的质子催化。

  DOI：

  10.1002/ejoc.201101307

文献信息

• High Activity and Efficient Turnover by a Simple, Self-Assembled “Artificial Diels–Alderase”
  作者：Vicente Martí-Centelles、Andrew L. Lawrence、Paul J. Lusby

  DOI：10.1021/jacs.7b12146

  日期：2018.2.28

  The Diels-Alder (DA) reaction is a cornerstone of synthesis, yet Nature does not use catalysts for intermolecular [4+2] cycloadditions. Attempts to create artificial "Diels-Alderases" have also met with limited success, plagued by product inhibition. Using a simple Pd2L4 capsule we now show DA catalysis that combines efficient turnover alongside enzyme-like hallmarks. This includes excellent activity

  Diels-Alder (DA) 反应是合成的基石，但自然界不使用催化剂进行分子间 [4+2] 环加成。制造人工“Diels-Alderases”的尝试也取得了有限的成功，受到产品抑制的困扰。使用一个简单的 Pd2L4 胶囊，我们现在展示了 DA 催化，它结合了高效的周转与酶样特征。这包括出色的活性（kcat/kuncat > 103）、与最熟练的 DA 催化抗体相当的选择性过渡态稳定性，以及对区域和化学选择性的控制，否则使用小分子催化剂难以实现。与其他使用合成胶囊的催化方法不同，这种方法不受熵效应的定义。相反，多个氢键相互作用调节反应性，
• Evaluation of a Nonresonant Microwave Applicator for Continuous-Flow Chemistry Applications
  作者：Per Öhrngren、Ashkan Fardost、Francesco Russo、Jon-Sverre Schanche、Magnus Fagrell、Mats Larhed

  DOI：10.1021/op300003b

  日期：2012.5.18

  successfully carried out using a 200 mm × ⌽ 3 mm tubular borosilicate reactor and a flow between 47 and 2120 μL/min. The microwave heating pattern was visualized with an IR camera. The transformations include palladium-catalyzed coupling reactions (oxidative Heck and Suzuki reactions), heterocyclic chemistry (oxathiazolone and Fischer indole synthesis), rearrangement (Claisen), and a Diels–Alder cycloaddition

  介绍并评估了用于连续流有机化学的非共振微波辐射器的概念。可以在2.4至2.5 GHz之间调节入射微波辐射的频率，以优化能量吸收率。反应温度由五个红外传感器监控，它们的信号可用于自动调节微波发生器的功率输出。已经探索了将几种不同的溶剂加热到比标准沸点高20°C的温度。使用200 mm×⌽3 mm的管状硼硅酸盐反应器并在47至2120μL/ min的流速下成功进行了几种不同的有机反应。微波加热模式用红外摄像机观察。转化包括钯催化的偶联反应（氧化性Heck和Suzuki反应），杂环化学（恶唑烷酮和菲舍尔吲哚合成），重排（克莱森）和Diels-Alder环加成反应。用Fischer吲哚反应进行的横向放大至57 mmol / h。
• A Lewis Acidity Scale in Relation to Rate Constants of Lewis Acid Catalyzed Organic Reactions
  作者：Gerhard Hilt、Florian Pünner、Juri Möbus、Vesal Naseri、Martin A. Bohn

  DOI：10.1002/ejoc.201101029

  日期：2011.10

  The quantification of Lewis acidity is accomplished by a deuterated quinolizidine probe utilizing 2H NMR spectroscopy. The chemical shifts of the 2H NMR signals for aluminum, boron, titanium, and zinc halides are reported. The rate constants for Lewis acid catalyzed reactions were determined by utilizing UV/Vis spectroscopy for Diels–Alder and Povarov reactions under pseudo-first-order conditions.

  路易斯酸度的量化是通过使用 2 H NMR 光谱的氘化喹唑啉探针完成的。报告了铝、硼、钛和锌卤化物的 2H NMR 信号的化学位移。路易斯酸催化反应的速率常数是通过在伪一级条件下利用紫外/可见光谱测定 Diels-Alder 和 Povarov 反应来确定的。2H NMR 化学位移的大小与以相同顺序研究的许多路易斯酸的有机转化速率常数相关，但确定了一些偏差。
• Rate enhancement of using silica gel as a practical, efficient grinding auxiliary to break π-π stacking under mechanochemical conditions
  作者：Cong Wang、Conghui Yue、Anthony Smith、James Mack

  DOI：10.1016/j.jorganchem.2022.122430

  日期：2022.10

  reactions and the physical properties revealed that the rate enhancement effect of silica gel appear to be based on a combination of surface charge, small particle size, acidity of silica gel and ability to absorb moisture. Among those factors, we think the most important factor is the strong surface charge of silica gel after grinding.

  作为一种实用、高效、易得、低成本的研磨助剂，硅胶在机械化学条件下可以打破π-π堆积。在涉及线性多环芳烃的多种类型的反应中，这种效应可能会导致显着的速率提高和产率。此外，为了深入了解研磨助剂在机械化学条件下的行为，在控制反应中使用了几种颗粒，并确定了不同的物理性质。控制反应和物理性质表明，硅胶的速率增强效应似乎是基于表面电荷、小粒径、硅胶的酸性和吸湿能力的综合作用。在这些因素中，我们认为最重要的因素是硅胶研磨后的强表面电荷。
• METHOD FOR PRODUCING XYLAN-CONTAINING MATERIAL
  申请人：Nippon Paper Industries Co., Ltd.

  公开号：EP3252083A1

  公开（公告）日：2017-12-06

  An object of the present invention is to provide a method for easily extracting and efficiently recovering xylan from wood. A xylan-containing material is produced by a method comprising the steps of: (a) adding an acid and/or carbon dioxide to a black liquor discharged during a soda cooking step of wood chips including hardwood chips to adjust the pH of the black liquor to be in the range of 1 to 9, thereby giving a suspension; (b) dehydrating and washing an insoluble matter generated in the suspension to separately collect the insoluble matter; and (c) adding an organic solvent to the insoluble matter obtained at the step (b) to give a suspension, and separately collecting a xylan-containing material made of the insoluble matter present in the suspension by solid/liquid separation.

  本发明的目的是提供一种从木材中轻松提取和高效回收木聚糖的方法。 含木聚糖材料的生产方法包括以下步骤(a) 向木片（包括硬木片）的苏打蒸煮步骤中排出的黑液中加入酸和/或二氧化碳，以调节黑液的 pH 值在 1 至 9 之间，从而得到悬浮液；(b) 脱水和洗涤悬浮液中产生的不溶物，以单独收集不溶物；(c) 向步骤(b)中得到的不溶物中加入有机溶剂，得到悬浮液，并通过固/液分离分别收集由悬浮液中的不溶物制成的含木糖材料。