2,6-二甲氧基蒽 | 36319-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2,6-二甲氧基蒽
• 英文名称: 2,6-dimethoxyanthracene
• 英文别名: 2,6-Dimethoxy-anthracen
• CAS: 36319-03-6
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: QCFQYVMTVPXVKG-UHFFFAOYSA-N

物化性质

• 熔点：
  262-264 °C
• 沸点：
  411.4±18.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于室温、干燥且密封的环境中。

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基蒽 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 2,6-bis(methylthio)-3,7-bis(trimethylsilylethynyl)anthracene
  参考文献：
  名称：

  Isomerically Pure Anthra[2,3-b:6,7-b′]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

  摘要：

  A new straightforward synthesis of isomerically pure anthra[2,3-b:6,7-b'] -difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS) from readily available 2,6-dimethoxyanthracene is described. The present successful synthesis makes it possible to overview the linear-shaped anti-acenedichalcogenophene compounds, that is, benzo[1,2-b:4,5-b']-, naphtho[2,3-b:6,7-b']-, and anthra[2,3-b:6,7-b']- difuran, -dithiophene, and -diselenophene. By comparing their electrochemical and photochemical properties, the electronic structures of acenedichalcogenophenes can be expressed as the outcome of balance between the central acene core and the outermost chalcogenophene rings. Among isomerically pure parent anti-anthradichalcogenophenes, anti-ADT and anti-ADS can afford crystalline thin films by vapor deposition, which acted as active layer in organic field-effect transistors with mobility as high as 0.3 cm(2) V-1 s(-1) for ADT and 0.7 cm(2) V-1 s(-1) for ADS. The mobility of isomerically pure anti-ADT is higher by several times than those reported for isomercally mixed ADT, implying that the isomeric purity could be beneficial for realizing the better FET mobility. We also tested the diphenyl derivatives of anti-ADF, -ADT, and -ADS as the active material for OFET devices, which showed high mobility of up to 1.3 cm(2) V-1 s(-1).

  DOI：

  10.1021/jo301438t
• 作为产物：
  描述：

  2,6-二羟基蒽醌 在 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 2,6-二甲氧基蒽
  参考文献：
  名称：

  烷氧基-9,10-蒽醌合成烷氧基蒽的新方法

  摘要：

  在回流乙酸中，锌可以将在不同位置la-h具有单、二和四醚基团的甲氧基-9,10-蒽醌直接还原为相应的甲氧基蒽3a-h，产率适中至良好。在类似条件下，酯基不受影响的 I'-蒽氧基乙酸乙酯 (3i) 和 1,8-氧基双(亚乙基氧基亚乙基氧基)蒽 (5) 也分别以 65% 和 70% 的产率方便地合成。

  DOI：

  10.1055/s-2003-42408

文献信息

• Synthesis of anthracene ethers from anthracene methyl ethers via an acid-catalyzed exchange reaction
  作者：Chih-Hsiu Lin、Krishnan Radhakrishnan

  DOI：10.1039/b412090f

  日期：——

  Selective synthesis of anthracene ethers was achieved under mild conditions via an acid-catalyzed ether-ether exchange reaction and its scope and limitations, as well as its potential in synthesizing anthracene-based crown ethers, tested.

  在温和的条件下，通过酸催化的醚-醚交换反应及其范围和局限性以及在合成基于蒽的冠状醚中的潜力，在温和条件下实现了对蒽醚的选择性合成。
• [EN] POLYMERS FOR USE IN ELECTRONIC DEVICES<br/>[FR] POLYMÈRES DESTINÉS À ÊTRE UTILISÉS DANS DES DISPOSITIFS ÉLECTRONIQUES
  申请人：DUPONT ELECTRONICS INC

  公开号：WO2020018617A1

  公开（公告）日：2020-01-23

  In Formula I: Qa is CRX, SiRx, GeRx, PRX, or N; Qb is CRy, SiRy, GeRy, PRy, or N; R1, R2, and R3 are the same or different at each occurrence and are F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, or siloxy, where adjacent R1 groups can be joined together to form a fused aromatic ring; Rx is H, F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, siloxy, or R6; Ry is H, F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, siloxy, or R7; R6 and R7 are the same or different and are NH2 ArNH2, or OArNH2; Ar is the same or different at each occurrence and is an unsubstituted or substituted C6-18 hydrocarbon aryl; m and n are the same or different and are an integer from 0-2, such that m + n < 2; x is an integer from 0-4; y and z are the same or different and are an integer from 0 to the maximum available.

  在公式I中：Qa是CRX，SiRx，GeRx，PRX或N；Qb是CRy，SiRy，GeRy，PRy或N；R1、R2和R3在每次出现时相同或不同，并且是F，CN，烷基，氟烷基，未取代或取代的碳氢基芳基，未取代或取代的杂环芳基，烷氧基，氟烷氧基，未取代或取代的芳氧基，硅烷基或硅氧基，其中相邻的R1基团可以结合在一起形成融合的芳香环；Rx是H，F，CN，烷基，氟烷基，未取代或取代的碳氢基芳基，未取代或取代的杂环芳基，烷氧基，氟烷氧基，未取代或取代的芳氧基，硅烷基，硅氧基或R6；Ry是H，F，CN，烷基，氟烷基，未取代或取代的碳氢基芳基，未取代或取代的杂环芳基，烷氧基，氟烷氧基，未取代或取代的芳氧基，硅烷基，硅氧基或R7；R6和R7相同或不同，并且是NH2 ArNH2或OArNH2；Ar在每次出现时相同或不同，并且是未取代或取代的C6-18碳氢基芳基；m和n相同或不同，并且是0-2的整数，使得m + n < 2；x是0-4的整数；y和z相同或不同，并且是0到最大可用的整数。
• Liquid crystalline dienophiles as regiochemical director in bimolecular Diels-Alder reactions
  作者：Tatsuya Yamaguchi、Takuro Yoshida、Tomohisa Nagamatsu、Takehisa Kunieda、Takeshi Honda、Masaaki Hirobe

  DOI：10.1016/s0040-4039(00)74315-2

  日期：1991.4

  The uncatalyzed cycloadditions of 2,6-dialkoxyanthracenes (2) to cholesteric liquid-crystalline fumarates (1) serving both as dienophiles and media resulted in highly regioselective formation of the syn-adducts (3)(70% d.e.).

  2，6-二烷氧基蒽（2）与胆甾型液晶富马酸酯（1）的未催化环加成导致双亲和物和介质的高度区域选择性形成了顺式加合物（3）（70％de）。
• Synthesis of Anthryl Sulfides from Anthryl Methyl Ethers via Acid-Catalyzed Ether-Sulfide Exchange Reaction
  作者：Chih-Hsiu Lin、Krishnan Radhakrishnan

  DOI：10.1055/s-2005-872268

  日期：——

  Under acidic condition, anthryl methyl ethers behave as anthryl cation synthons and undergo ipso-substitution to produce anthryl sulfides. These compounds are hard to access with currently available methodology and they have great potentials as organic electronic materials.

  在酸性条件下，蒽基甲基醚表现为蒽基阳离子合成子，并进行同位取代以产生蒽基硫化物。这些化合物很难用目前可用的方法获得，它们作为有机电子材料具有巨大的潜力。
• Optical activity of C2 symmetrical 9,10-dihydro-9,10-ethanoanthracenes
  作者：S. Hagishita、K. Kuriyama

  DOI：10.1016/0040-4020(72)88028-1

  日期：1972.1

  Optically active C2-symmetrical 9,10-dihydro-9,10-ethanoanthracene (DEA) derivatives have been prepared and their absolute configurations determined by kinetic resolution of phenylmethylcarbinol with optically active DEA-11,12-dicarboxylic acid chloride, spectroscopic studies and chemical correlations. The rotational strengths for the α- and the p-band regions calculated from the dipole-velocity procedure

  制备了旋光的C 2对称的9,10-二氢-9,10-乙基蒽（DEA）衍生物，并通过用旋光的DEA-11,12-二羧酸氯化物动力学拆分苯基甲基甲醇确定了它们的绝对构型，并进行了光谱研究和化学相关性。α-和p的旋转强度由π-SCF近似中的偶极速度过程计算出的带区，而不是点偶极激子处理，与实验吻合良好。尽管旋转强度主要是由局部激励的耦合产生的，但在某些情况下，电荷转移构型会导致A和B组合的跃迁能顺序在励磁构型中发生反转。这是基于激子近似的实验结果和计算结果之间不一致的最重要因素，其中假定两个发色团之间没有电子交换。