2-(hydroxymethyl)-9,10-dimethyloxyanthracene | 280764-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(hydroxymethyl)-9,10-dimethyloxyanthracene
• 英文别名: 2-(hydroxymethyl)-9,10-dimethoxyanthracene；2-hydroxymethyl-9,10-dimethoxyanthracene；(9,10-Dimethoxyanthracen-2-yl)methanol
• CAS: 280764-63-8
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: ZMDDTYNGSUCZIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-9,10-dimethyloxyanthracene 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 cerium(III) chloride 、 四丁基氟化铵 、 四氯化钛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 苯 为溶剂， 反应 10.5h， 生成 (±)-zenkequinone B
  参考文献：
  名称：

  The first total synthesis of (±)-zenkequinone B

  摘要：

  The first total synthesis of tetrahydrobenzo[a]anthraquinone natural product (+/-)-zenkequinone B (1) is reported. The key step involves the TiCl(4)-promoted intramolecular cyclization of 4-aryl-2-hydroxybutanal diethyl acetal 4 to give compound 3. The total synthesis of (+/-)-zenekequinone B (1) has been accomplished in five steps from readily available 2-(chloromethyl)-9,10-dimethoxyanthracene (5) in 40.3% overall yield. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2011.02.103
• 作为产物：
  描述：

  2-羟甲基蒽醌 、 碘甲烷 在 sodium dithionite 作用下， 生成 2-(hydroxymethyl)-9,10-dimethyloxyanthracene
  参考文献：
  名称：

  供体-受体系统中的远距离分子内光诱导的电子转移：放热对电子转移速率的影响

  摘要：

  通过荧光猝灭实验研究了在长距离分隔的供体-受体系统中光诱导的分子内电子转移。在高度放热的反应中观察到电子传递速率常数降低，这表明存在“倒置区域”，这与马库斯模型一致。

  DOI：

  10.1039/c39920000669

文献信息

• Long distance intramolecular photoinduced electron transfer in donor–acceptor systems: effect of exothermicity on electron-transfer rates
  作者：Sheng-ze Zhou、Shu-yin Shen、Qing-fu Zhou、Hui-jun Xu

  DOI：10.1039/c39920000669

  日期：——

  Photoinduced intramolecular electron transfer in donor–acceptor systems separated by a long distance are studied by fluorescence quenching experiments; reduced rate constants for electron transfer are observed in highly exothermic reactions, which indicates the existence of an ‘inverted region’, in accord with Marcus' model.

  通过荧光猝灭实验研究了在长距离分隔的供体-受体系统中光诱导的分子内电子转移。在高度放热的反应中观察到电子传递速率常数降低，这表明存在“倒置区域”，这与马库斯模型一致。
• Self-Assembly of Electron Donor−Acceptor Dyads into Ordered Architectures in Two and Three Dimensions:  Surface Patterning and Columnar “Double Cables”
  作者：Paolo Samorì、Xiaomin Yin、Natalia Tchebotareva、Zhaohui Wang、Tadeusz Pakula、Frank Jäckel、Mark D. Watson、Alessandro Venturini、Klaus Müllen、Jürgen P. Rabe

  DOI：10.1021/ja038648+

  日期：2004.3.1

  We report the synthesis and characterization of covalent dyads and multiads of electron acceptors (A) and donors (D), with the purpose of exploiting their nanophase separation behavior toward (a) two-dimensional (2D) surface patterning with well-defined integrated arrays of dissimilar molecular electronic features and (b) bulk self-assembly to noncovalent columnar versions of the so-called "double cable" systems, the likes of which could eventually provide side-by-side percolation pathways for electrons and holes in solar cells. Soluble, alkylated hexa-peri-hexabenzocoronenes (HBCs) bearing tethered anthraquinones (AQs) are shown by scanning tunneling microscopy (STM) to self-assemble at the solution -graphite interface into either defect-rich polycrystalline monolayers or extended 2D crystalline domains, depending on the number of tethered AQs. In the bulk, the thermal stability of the room-temperature HBC columnar phase is increased, which is attributed to the desired nanotriphase separation of HBC columns, insulating alkyl sheaths, and AQ units. Homeotropic alignment (columns normal to surfaces), predicted to be ideal for potential exploitation of such "double cables" in photovoltaic devices, is demonstrated.
• Jiang, Hua; Xu, Huijun; Ye, Jianping, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 5, p. 925 - 930
  作者：Jiang, Hua、Xu, Huijun、Ye, Jianping

  DOI：——

  日期：——
• The first total synthesis of (±)-zenkequinone B
  作者：Rammohan Devulapally、Yung-Son Hon

  DOI：10.1016/j.tetlet.2011.02.103

  日期：2011.6

  The first total synthesis of tetrahydrobenzo[a]anthraquinone natural product (+/-)-zenkequinone B (1) is reported. The key step involves the TiCl(4)-promoted intramolecular cyclization of 4-aryl-2-hydroxybutanal diethyl acetal 4 to give compound 3. The total synthesis of (+/-)-zenekequinone B (1) has been accomplished in five steps from readily available 2-(chloromethyl)-9,10-dimethoxyanthracene (5) in 40.3% overall yield. (C) 2011 Published by Elsevier Ltd.