1,2,7,8-Dibenzo-3,4,5,6-tetrahydroxanthylium-perchlorat | 6581-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 1,2,7,8-Dibenzo-3,4,5,6-tetrahydroxanthylium-perchlorat
• 英文别名: Dibenzo(c,h)xanthylium, 5,6,8,9-tetrahydro-, perchlorate；2-oxoniapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4,6,8,13,17,19,21-nonaene;perchlorate
• CAS: 6581-93-7
• 化学式: C₂₁H₁₇O*ClO₄
• 分子量: 384.816
• InChiKey: DSDGMNTVKNEPIW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,7,8-Dibenzo-3,4,5,6-tetrahydroxanthylium-perchlorat 在 正丁基锂 、 高氯酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 7-Benzyl-5,6,8,9-tetrahydro-dibenzo[c,h]xanthenylium; perchlorate
  参考文献：
  名称：

  Benzotriazole-Mediated Conversions of para-H-Substituted Pyrylium, Benzo[b]pyrylium, and Xanthylium Salts into para-Position Functionalized Derivatives (An Indirect Electrophilic Substitution of Electron-Deficient Heteroaromatics)

  摘要：

  4H-Substituted pyrylium 9, benzo[b]pyrylium 15, and xanthylium salts 22 react with benzotriazole to give the corresponding 4H-(benzotriazol-l-yl)pyrans 10, benzo[b]pyrans 16, or xanthenes 23. Novel anion precursors 10, 16, and 23 undergo smooth lithiations at the positions a to the benzotriazol-1-yl function, i.e., at the para-position of the O-heterosycle. Subsequent trapping with different alkyl halides gives intermediates 14, 21, and 25, which are converted by mineral acid into para-functionalized pyrylium 11-13, benzo[b]pyrylium 17-20, and the xanthylium 24 salts in good to excellent yields.

  DOI：

  10.1021/jo971174a
• 作为产物：
  描述：

  1-氯-3,4-二氢-2-萘甲醛 、 3,4-二氢-1(2H)-萘酮 在 高氯酸 作用下， 以 甲苯 为溶剂， 生成 1,2,7,8-Dibenzo-3,4,5,6-tetrahydroxanthylium-perchlorat
  参考文献：
  名称：

  A Systematic Design and Synthesis of PET‐based Fluorescent Probes for Monitoring pH During Mitophagy

  摘要：

  摘要 线粒体是细胞的动力源，在 pH ∼ 8.0 的条件下发挥功能。线粒体功能失调，包括线粒体损伤，会导致 pH 值改变。因此，研究人员致力于开发高效的 pH 探针来跟踪线粒体的 pH 动态。在此，我们开发了一种基于 PET 的荧光探针，用于监测线粒体功能障碍时的 pH 值。我们在五环吡啶荧光团中合成了三种具有可变间隔长度的衍生物（PM-C2、PM-C3 和 PM-C6）。与其他两种衍生物相比，PM-C2 能有效地从受体（叔胺）转移电子。当叔胺在酸性 pH 值下质子化时，这一 PET 过程受到抑制。然而，PM-C3 在类似条件下的荧光强度很小，而 PM-C6 的变化几乎可以忽略不计，这表明这两种衍生物的 PET 过程都很差。此外，DFT/TD-DFT 量子化学计算也很好地支持了这种光学现象和 PET 过程。具有生物相容性、光稳定性和线粒体特异性的 PM-C2 可监测线粒体损伤过程中的 pH 动态，线粒体损伤会被溶酶体吞噬，这也被称为有丝分裂。雷帕霉素和饥饿诱导了这种丝裂吞噬过程，可通过开启荧光增强来监测这一过程。使用我们开发的探针跟踪 Parkin 蛋白从细胞质到受损线粒体的转运，进一步验证了这一过程。

  DOI：

  10.1002/asia.202300308

文献信息

• Tripathi, S.; Simalty, M.; Pouliquen, J., Bulletin de la Societe Chimique de France, 1986, # 4, p. 600 - 612
  作者：Tripathi, S.、Simalty, M.、Pouliquen, J.、Kossanyi, J

  DOI：——

  日期：——
• FEDOTOVA, O. V.;LUBOTSKAYA, T. A.;KRIVENKO, A. P., ISSLED. OBL. SINTEZA I KATALIZA ORGAN. SOEDIN., CAPATOB, 1983, 9-13
  作者：FEDOTOVA, O. V.、LUBOTSKAYA, T. A.、KRIVENKO, A. P.

  DOI：——

  日期：——
• Benzotriazole-Mediated Conversions of <i>para</i>-H-Substituted Pyrylium, Benzo[<i>b</i>]pyrylium, and Xanthylium Salts into <i>para</i>-Position Functionalized Derivatives (An Indirect Electrophilic Substitution of Electron-Deficient Heteroaromatics)
  作者：Alan R. Katritzky、Peter Czerney、Julian R. Levell

  DOI：10.1021/jo971174a

  日期：1997.11.1

  4H-Substituted pyrylium 9, benzo[b]pyrylium 15, and xanthylium salts 22 react with benzotriazole to give the corresponding 4H-(benzotriazol-l-yl)pyrans 10, benzo[b]pyrans 16, or xanthenes 23. Novel anion precursors 10, 16, and 23 undergo smooth lithiations at the positions a to the benzotriazol-1-yl function, i.e., at the para-position of the O-heterosycle. Subsequent trapping with different alkyl halides gives intermediates 14, 21, and 25, which are converted by mineral acid into para-functionalized pyrylium 11-13, benzo[b]pyrylium 17-20, and the xanthylium 24 salts in good to excellent yields.
• A Systematic Design and Synthesis of PET‐based Fluorescent Probes for Monitoring pH During Mitophagy
  作者：Rashmi Yadav、Subrata Munan、Mudassar Ali、Koyeli Mapa、Animesh Samanta

  DOI：10.1002/asia.202300308

  日期：2023.6.15

  Mitochondria are the powerhouse of the cell and function at pH ∼8.0. Dysfunctions of mitochondria, includes mitochondrial damage, leading to pH alteration. Hence, researchers aim to develop efficient pH probes for tracking mitochondrial pH dynamics. Herein, we developed a PET‐based fluorescent probe for pH monitoring during mitochondrial dysfunctions. Three derivatives were synthesized with a variable spacer's length in pentacyclic pyridinium fluorophores (PM‐C2, PM‐C3, and PM‐C6). An efficient electron transfers from the receptor (tertiary amine) was observed in the case of PM‐C2 compared to the other two derivatives. This PET process was inhibited when tertiary amine was protonated in acidic pH. However, PM‐C3 showed minimal fluorescence intensity at similar conditions and almost negligible change in case of PM‐C6, suggesting poor PET process for both the derivatives. Furthermore, DFT/TD‐DFT quantum chemical calculation well supported this optical phenomena and PET process. Biocompatible, photostable, and mitochondria‐specific PM‐C2 could monitor pH dynamics during mitochondrial damage which were engulfed by lysosome, also known as mitophagy. This mitophagy process were induced by rapamycin and starvation, which can be monitored by turn‐on fluorescence enhancement. This process was further validated by tracking Parkin‐protein translocation from cytoplasm to damaged mitochondria using our developed probe.

  摘要 线粒体是细胞的动力源，在 pH ∼ 8.0 的条件下发挥功能。线粒体功能失调，包括线粒体损伤，会导致 pH 值改变。因此，研究人员致力于开发高效的 pH 探针来跟踪线粒体的 pH 动态。在此，我们开发了一种基于 PET 的荧光探针，用于监测线粒体功能障碍时的 pH 值。我们在五环吡啶荧光团中合成了三种具有可变间隔长度的衍生物（PM-C2、PM-C3 和 PM-C6）。与其他两种衍生物相比，PM-C2 能有效地从受体（叔胺）转移电子。当叔胺在酸性 pH 值下质子化时，这一 PET 过程受到抑制。然而，PM-C3 在类似条件下的荧光强度很小，而 PM-C6 的变化几乎可以忽略不计，这表明这两种衍生物的 PET 过程都很差。此外，DFT/TD-DFT 量子化学计算也很好地支持了这种光学现象和 PET 过程。具有生物相容性、光稳定性和线粒体特异性的 PM-C2 可监测线粒体损伤过程中的 pH 动态，线粒体损伤会被溶酶体吞噬，这也被称为有丝分裂。雷帕霉素和饥饿诱导了这种丝裂吞噬过程，可通过开启荧光增强来监测这一过程。使用我们开发的探针跟踪 Parkin 蛋白从细胞质到受损线粒体的转运，进一步验证了这一过程。