1,5-dihydroxy-2,3,6,7-tetraoctyloxy-9,10-anthraquinone | 205243-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5-dihydroxy-2,3,6,7-tetraoctyloxy-9,10-anthraquinone
• 英文别名: 1,5-Dihydroxy-2,3,6,7-tetraoctoxyanthracene-9,10-dione
• CAS: 205243-39-6
• 化学式: C₄₆H₇₂O₈
• 分子量: 753.073
• InChiKey: FOJHICSFBVZTRK-UHFFFAOYSA-N

物化性质

• 沸点：
  831.8±65.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  54
• 可旋转键数：
  32
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,5-dihydroxy-2,3,6,7-tetraoctyloxy-9,10-anthraquinone 在 4-甲基苯磺酸吡啶 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,5-Bis-(2-hydroxy-ethoxy)-2,3,6,7-tetrakis-octyloxy-anthraquinone
  参考文献：
  名称：

  Synthesis and Mesomorphic Properties of Some Anthraquinone Derivatives: New Difunctionalised Discotic Monomers

  摘要：

  Some new 9,10-anthraquinone (rufigallol) derivatives have been prepared and their mesomorphic properties have been studied. The unsymmetrically substituted tetrahydropyranyloxy-ethers (THP-ethers), exhibited columnar mesomorphism at fairly low temperatures and the xray studies carried out for one of the homologues confirmed the hexagonal nature of the mesophase. The deprotected derivatives of these THP-ethers, also form columnar mesophases. All these derivatives are very good candidates for polymerisation studies.

  DOI：

  10.1080/10587250008025232
• 作为产物：
  描述：

  没食子酸 在 硫酸 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 1,5-dihydroxy-2,3,6,7-tetraoctyloxy-9,10-anthraquinone
  参考文献：
  名称：

  新型基于蒽醌的盘状液晶的相行为

  摘要：

  五个新颖柱状液晶化合物（4.1 - 4.5）由携带4支烷氧基链（R =中央蒽醌芯的Ñ -C 6 ħ 13，Ñ -C 8 ħ 17，Ñ -C 10 ħ 21，Ñ -C 12 ħ 25合成了具有两个对角相对的1-乙炔基-4-戊基苯单元的3,7-二甲基辛基），并研究了它们在分子结构变化和自组装成柱状中间相之间的相变。进行了小角度和广角X射线散射（SAXS / WAXS）研究，以推断中间相的确切性质，并且从衍射图样中观察到的峰强度得出了它们相应的电子密度图。对具有不同烷氧基链的化合物进行的比较表明，对于较短的外围烷氧基链，软晶柱状矩形（Cr colrec）相在较低温度下是稳定的（4.1； R = n -C 6 H 13），发现随着温度的升高，呈现柱状六方相（Col h），然后呈现盘状向列相（N D）。相反，增加外围链长Ñ -C 8 ħ 17或支链酮（4.2和4.5）稳定山口ħ相在较低温度下，并显示

  DOI：

  10.1021/acs.langmuir.7b03031

文献信息

• Syntheses and Mesogenic Properties of Dimers and Trimers Consisting of Triphenylene Donor and Anthraquinone Acceptor
  作者：Sanjay Kumar Varshney、Hiroki Nagayama、Veena Prasad、Hideo Takezoe

  DOI：10.1080/15421400903483908

  日期：2010.2.25

  microscope (POM) and differential scanning calorimetry (DSC). The dimers D-A(OH) having the spacer length similar to peripheral alkoxy chains exhibit the nematic (N) phase, whereas dimers D-A(OH) and D-A(OAc) having longer spacer length compared with peripheral alkoxy chains exhibit the columnar (Col) phase. The trimers exhibit N or Col mesophases, as confirmed by X-ray diffraction (XRD) studies, according

  报道了新二聚体的合成和液晶特性，其具有通过柔性间隔物连接到单官能化蒽醌受体 (A) 核 DA 的三亚苯供体 (D) 核。这些二聚体具有羟基 (DA(OH)) 或乙酰氧基 (DA(OAc)) 官能团。此处还报告了线性三聚体 DAD。这些二聚体和三聚体的化学结构通过光谱和光谱分析表征。通过偏光显微镜（POM）和差示扫描量热法（DSC）研究液晶性质。间隔长度与外围烷氧基链相似的二聚体 DA(OH) 呈现向列 (N) 相，而间隔长度比外围烷氧基链长的二聚体 DA(OH) 和 DA(OAc) 呈现柱状 (Col) 相. 根据与 DA 中类似的规则，如 X 射线衍射 (XRD) 研究所证实的，三聚体表现出 N 或 Col 中间相。因此，间隔长度和官能团对分子自组装的影响更大，从而表现出液晶特性。值得注意的是，这些二聚体和三聚体中的一些在室温下显示出 N 或 Col 相。据我们所知，这是第一个具有非分支但正常外围链的分子。
• Microwave-assisted facile synthesis of discotic liquid crystalline symmetrical donor–acceptor–donor triads
  作者：Satyam Kumar Gupta、V. A. Raghunathan、Sandeep Kumar

  DOI：10.1039/b808750d

  日期：——

  We report the synthesis and characterization of two series of novel triphenylene–anthraquinone-based symmetric discotic liquid crystalline trimers. These triads were prepared using microwave dielectric heating. Conventional heating under similar reaction conditions failed to produce desired products. To the best of our knowledge, these are the first donor–acceptor–donor triads in which all the three components represent discotic mesogenic moieties. Chemical structures of these discotic oligomers have been characterized by spectral techniques and elemental analysis. The thermotropic liquid crystalline properties of these donor–acceptor–donor triads were investigated by polarizing optical microscopy and differential scanning calorimetry. They exhibit a columnar mesophase over a wide range of temperature. The columnar hexagonal mesophase structure of these discotic oligomers has been elucidated with the help of X-ray diffraction studies.

  我们报告了两系列新型三萘烯-蒽醌基对称盘状液晶三聚体的合成与表征。这些三聚体是通过微波介电加热制备的。在类似反应条件下，常规加热未能产生预期的产物。据我们所知，这是首个所有三种组分均为盘状中间体的给体-受体-给体三聚体。这些盘状 oligomers 的化学结构已通过光谱技术和元素分析进行了表征。这些给体-受体-给体三聚体的热致液晶性质通过偏光显微镜和差示扫描量热法进行了研究。它们在广泛的温度范围内展现出柱状中相。借助 X 射线衍射研究，我们阐明了这些盘状 oligomers 的柱状六角中相结构。
• Microwave-assisted synthesis of rufigallol and its novel room-temperature liquid crystalline derivatives
  作者：Hari Krishna Bisoyi、Sandeep Kumar

  DOI：10.1016/j.tetlet.2007.04.094

  日期：2007.6

  An efficient, simple, rapid and economic microwave-assisted synthesis of rufigallol, a molecule of both biological and physical interest, is reported. The acid-catalyzed self-condensation of gallic acid under microwave irradiation produces rufigallol in high yield within 90 s. Alkylation of rufigallol with branched-chain alkyl halides under microwave irradiation provides novel room-temperature discotic

  据报道，高效，简单，快速和经济的微波辅助合成的rufigallol是一种具有生物学和物理意义的分子。在微波辐射下，酸催化的没食子酸的自缩合可在90 s内以高收率产生三氟萘洛尔。在微波辐射下，rufigallol与支链烷基卤化物的烷基化以优异的产率提供了新型的室温盘状液晶。
• Multifunctional Spin-carrying Anthraquinone Derivatives
  作者：Yuuki Shibata、Hiroki Akutsu、Jun-ichi Yamada、Masaharu Satoh、Uma S. Hiremath、Channabasaveshwar V. Yelamaggad、Shin’ichi Nakatsuji

  DOI：10.1246/cl.2010.671

  日期：2010.7.5

  Several nitroxide radicals derived from 2,3,6,7-tetraalkoxy-9,10-anthraquinone core have been prepared and their magnetic, redox as well as battery properties are studied. Notably, one of the derivatives with a mono-PROXYL-radical substituent exhibits a fairly stable multistep charge–discharge process and a heat-responsive magnetic behavior.

  研究人员制备了几种以 2,3,6,7- 四烷氧基-9,10-蒽醌为核心的亚硝基自由基，并研究了它们的磁性、氧化还原性以及电池特性。值得注意的是，其中一种具有单-丙氧基-自由基取代基的衍生物表现出相当稳定的多级充放电过程和热响应磁性。
• An Efficient Synthesis, and Characterisation of Anthraquinone-based Discotic Liquid Crystals and Their X-Ray Diffraction Studies
  作者：K. Krishnan、V. S. K. Balagurusamy

  DOI：10.1080/10587250008025228

  日期：2000.10.1

  We herein report an efficient synthesis of 1,2,3.5,6.7-hexaalkoxy-9,10-anthraquinones (also called rufigallol hexaethers) starting from gallic acid. These ethers are known to form columnar phases which are suitable for the study of charge transport, photoconductivity etc. Our X-ray diffraction studies show that the high-temperature mesophase is hexagonal columnar with correlation among the molecular cores alone the column (Col(h), also called Dh) and that, identified for the first time in these systems, there are one or two additional mesophases at low temperature depending on the system, some of them three-dimensionally ordered. Our results show that the mesophase thigh-temperature) range does not dramatically decrease as the length of the alkyl chains at the 1.5 positions become longer than the rest. Since these molecules have absorption in the visible region they may also be the potential candidates for studying photovoltaic effects that are of interest in developing energy conversion applications.