3,8-dihydroxypyrene-1,6-dione | 74725-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 3,8-dihydroxypyrene-1,6-dione
• 英文别名: 3,8-dihydroxypyrene-1,6-quinone
• CAS: 74725-71-6
• 化学式: C₁₆H₈O₄
• 分子量: 264.237
• InChiKey: WXAPAZYYOVHUBO-UHFFFAOYSA-N

物化性质

• 沸点：
  579.7±50.0 °C(Predicted)
• 密度：
  1.746±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,8-dihydroxypyrene-1,6-dione 在 对甲苯磺酰叠氮 、 次氯酸叔丁酯 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 (2,7-dichloro-7-formyloxy-1,3,6,8-tetraoxopyren-2-yl) formate
  参考文献：
  名称：

  Gleiter, Rolf; Schang, Peter, Angewandte Chemie, 1980, vol. 92, # 9, p. 768 - 769

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,6,8-四氯芘 在 硫酸 、 三氧化硫 作用下， 以96%的产率得到3,8-dihydroxypyrene-1,6-dione
  参考文献：
  名称：

  具有芘二酮核的新型 π 受体盘状液晶化合物的合成和相结构

  摘要：

  以芘二酮单元为核心合成了几种π受体盘状液晶化合物。通过偏振光学显微镜 (POM) 观察和 XRD 测量揭示了梯田状和带状结构。结合类似结晶化合物的单晶结构分析结果，确认所有液晶化合物形成盘状层状相DL2。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800360

文献信息

• Access to Functionalized Pyrenes, Peropyrenes, Terropyrenes, and Quarterropyrenes via Reductive Aromatization
  作者：Simon Werner、Tobias Vollgraff、Jörg Sundermeyer

  DOI：10.1002/anie.202100686

  日期：2021.6.7

  versatile concept for the synthesis of fourfold functionalized, soluble pyrenes, peropyrenes, terropyrenes, and quarterropyrenes. They were obtained by a modular stepwise approach towards the rylene scaffold via Suzuki–Miyaura cross coupling, oxidative cyclodehydrogenation in the presence of caesium hydroxide under air, and finally zinc-mediated reductive silylation. The silylated reaction products were

  在本文中，我们报告了一种用于合成四重功能化的可溶性芘、过芘、terropyrene 和四分之一芘的通用概念。它们是通过 Suzuki-Miyaura 交叉偶联、在氢氧化铯存在下在空气中氧化环化脱氢以及最终锌介导的还原性硅烷化，通过模块化逐步方法获得的。硅烷化反应产物通过 X 射线晶体学表征。介绍了合成和结晶的季芘的第一个例子，并研究了它的氧化反应。通过 UV/Vis-NIR 和光致发光光谱系统地表征了功能化的 ropyrene，显示每个萘单元的红移 80 nm 和消光系数几乎线性增加。
• Induction and Control of Columnar Mesophase by Charge Transfer Interaction and Side Chain Structures of Tetrasubstituted Pyrenes
  作者：Takuji Hirose、Osamu Kawakami、Mikio Yasutake

  DOI：10.1080/154214090960081

  日期：2006.8.1

  The induction of the columnar phase is described in which intrinsically crystalline 1,4,6,9-tetraacyloxypyrenes have been mixed with tetranitrofluorenone, TeNF, as an electron acceptor. The pyrene derivative with linear nonyl chains, PC9, has not shown any mesophases using trinitrofluorenone, suggesting that stronger charge transfer interaction is favored by TeNF. The shape of the substituents works to control the mesophase type: the mixture of PC9 and TeNF has formed a rectangular columnar phase, and a hexagonal columnar phase is attained by rounder derivatives bearing branched side chains.
• Shigalevskii, V. A.; Chesnovskii, V. S.; Filippov, M. P., Journal of Organic Chemistry USSR (English Translation), 1985, p. 1373 - 1379
  作者：Shigalevskii, V. A.、Chesnovskii, V. S.、Filippov, M. P.、Solomatin, G. G.

  DOI：——

  日期：——
• Liquid-Crystalline Behavior and Structure of Charge-Transfer Complexes of Pyrene Derivatives with Four Linear Alkanoyloxy Substituents
  作者：Takuji Hirose、Takuya Yumoto、Kozue Matsumoto、Satomi Mitsushio、Osamu Kawakami、Mikio Yasutake

  DOI：10.1080/15421406.2010.484613

  日期：2010.6.21

  Pyrene derivatives (PCns) bearing four linear alkanoyloxy chains (n=7, 9, 11, 15) were synthesized and shown to exhibit mesophases as a result of forming charge-transfer (CT) complexes with strongly electron-accepting 2,4,5,7-tetranitro-9-fluorenone (TeNF). The mesomorphic properties were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and variable-temperature X-ray diffraction (XRD) studies. The discotic lamellar phase was confirmed by XRD measurements, but no indication of intercalation of TeNF was observed. The CT complexation was supported by not only spectroscopic studies but the thermal behavior of the co-ground mixture.
• GLEITER R.; SCHANG P., ANGEW. CHEM., 1980, 92, NO 9, 768-769
  作者：GLEITER R.、 SCHANG P.

  DOI：——

  日期：——