2,6-bis(2-hydroxyethyloxy)-9,10-anthraquinone | 500004-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-bis(2-hydroxyethyloxy)-9,10-anthraquinone
• 英文别名: 2,6-bis[(hydroxyethyl)oxy]anthraquinone；2,6-Bis(2-hydroxyethoxy)anthraquinone；2,6-bis(2-hydroxyethoxy)anthracene-9,10-dione
• CAS: 500004-01-3
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: CZXLNSNTTDAVKE-UHFFFAOYSA-N

物化性质

• 沸点：
  593.1±50.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-bis(2-hydroxyethyloxy)-9,10-anthraquinone 在 吡啶 、 咪唑 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 9,10-bis(4,5-dimethylthio-1,3-dithiol-2-ylidene)-2,6-bis(1,4,8-trioxa-5,7-dioxodecyl)-9,10-dihydroanthracene
  参考文献：
  名称：

  Synthesis and Properties of Bingel-type Methanofullerene−π-Extended-TTF Diads and Triads

  摘要：

  Novel C-60/pi-extended tetrathiafulvalene (exTTF) diads (12a-c) and triads [D(2)A (14a-c) and DA(2) (25, 27a-c)] have been synthesized by the Bingel cyclopropanation reaction of the respective exTTF-containing malonates and [60]fullerene. The reaction of exTTF-bismalonates with C-60 affords the respective C-60-exTTF diads (26a-c) together with the triad C-60-exTTF-C-60 (25, 27a-c) and a regioisomeric mixture of bisadducts (28b-c). Theoretical calculations (PM3) predict the favored geometry for triads 14a-c depending upon the orientation (up and down) of the 1,3-dithiole rings in the exTTFs, as well as the more stable regioisomers for the bisadducts 28. Cyclic voltammetry measurements reveal that C-60 and exTTF units do not intereact in the ground state. Compounds 26a-c and 27a-c are not electrochemically stable. A photoinduced electron transfer leading to the formation of the radical pair (C-60(-)-exTTF(.+)) has been observed for compounds 14a-c.

  DOI：

  10.1021/jo020412l
• 作为产物：
  描述：

  2,6-bis(2-hydroxyethoxy)anthrquinone 、 1-bromoethanol 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 生成 2,6-bis(2-hydroxyethyloxy)-9,10-anthraquinone
  参考文献：
  名称：

  Bis-basic ethers of 2,6- and 2,7-dihydroxyanthraquinones

  摘要：

  本文披露了具有抗病毒活性的新化合物和制药配方。所披露的化合物具有以下结构式：其中一个R.sup.2是氢原子，另一个R.sup.2是基团A，A是具有2或3个碳原子的直链烷基基团，每个R.sup.3和R.sup.4是氢原子，具有1至3个碳原子的烷基基团，或者每组R.sup.3和R.sup.4与它们连接的氮原子一起形成饱和的单环杂环基团。还包括这些碱的酸盐。这些化合物可以通过描述的各种方法制备。

  公开号：

  US03974186A1

文献信息

• Anthraquinones as Artificial DNA Building Blocks
  作者：Nicolas Bouquin、Vladimir L. Malinovskii、Robert Häner

  DOI：10.1002/ejoc.200800080

  日期：2008.5

  Synthesis and properties of oligodeoxynucleotides containing anthraquinone-derived building blocks with flexible linkers are described. Starting from the 1,4-, 1,5-, 1,8- and 2,6-dihydroxyanthraquinone isomers, the corresponding phosphoramidites were prepared and incorporated into oligonucleotides. The site of linker attachment was found to be of critical importance for hybrid stability. Whereas the

  描述了含有蒽醌衍生结构单元和柔性接头的寡脱氧核苷酸的合成和性质。从 1,4-、1,5-、1,8- 和 2,6- 二羟基蒽醌异构体开始，制备相应的亚磷酰胺并将其掺入寡核苷酸中。发现接头附着位点对于杂交稳定性至关重要。虽然 2,6-异构体导致显着的稳定性，但所有其他异构体对双链体的稳定性有负面影响。光谱研究表明蒽醌类具有荧光猝灭剂的作用。提出了蒽醌修饰的双链杂种模型。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• US3974186A
  申请人：——

  公开号：US3974186A

  公开（公告）日：1976-08-10
• US4073904A
  申请人：——

  公开号：US4073904A

  公开（公告）日：1978-02-14
• Bis-basic ethers of 2,6- and 2,7-dihydroxyanthraquinones
  申请人：Richardson-Merrell Inc.

  公开号：US03974186A1

  公开（公告）日：1976-08-10

  Disclosed are novel compounds and pharmaceutical formulations having antiviral activity. The disclosed compounds have the formula ##SPC1## Wherein one R.sup.2 is a hydrogen atom and the other R.sup.2 is the radical ##SPC2## A is a straight chain alkylene group having 2 or 3 carbon atoms and each R.sup.3 and R.sup.4 is a hydrogen atom, an alkyl radical having 1 to 3 carbon atoms or each set of R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached is a saturated monocyclic heterocyclic group. Also included are the acid addition salts of these bases. These compounds may be prepared by various methods which are described.

  本文披露了具有抗病毒活性的新化合物和制药配方。所披露的化合物具有以下结构式：其中一个R.sup.2是氢原子，另一个R.sup.2是基团A，A是具有2或3个碳原子的直链烷基基团，每个R.sup.3和R.sup.4是氢原子，具有1至3个碳原子的烷基基团，或者每组R.sup.3和R.sup.4与它们连接的氮原子一起形成饱和的单环杂环基团。还包括这些碱的酸盐。这些化合物可以通过描述的各种方法制备。
• Synthesis and Properties of Bingel-type Methanofullerene−π-Extended-TTF Diads and Triads
  作者：Susana González、Nazario Martín、Dirk M. Guldi

  DOI：10.1021/jo020412l

  日期：2003.2.1

  Novel C-60/pi-extended tetrathiafulvalene (exTTF) diads (12a-c) and triads [D(2)A (14a-c) and DA(2) (25, 27a-c)] have been synthesized by the Bingel cyclopropanation reaction of the respective exTTF-containing malonates and [60]fullerene. The reaction of exTTF-bismalonates with C-60 affords the respective C-60-exTTF diads (26a-c) together with the triad C-60-exTTF-C-60 (25, 27a-c) and a regioisomeric mixture of bisadducts (28b-c). Theoretical calculations (PM3) predict the favored geometry for triads 14a-c depending upon the orientation (up and down) of the 1,3-dithiole rings in the exTTFs, as well as the more stable regioisomers for the bisadducts 28. Cyclic voltammetry measurements reveal that C-60 and exTTF units do not intereact in the ground state. Compounds 26a-c and 27a-c are not electrochemically stable. A photoinduced electron transfer leading to the formation of the radical pair (C-60(-)-exTTF(.+)) has been observed for compounds 14a-c.