5,23-Dimethoxy-14-oxahexacyclo[15.8.0.02,11.03,8.012,16.020,25]pentacosa-1(17),2(11),3(8),4,6,12(16),20(25),21,23-nonaene-13,15-dione | 1366018-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5,23-Dimethoxy-14-oxahexacyclo[15.8.0.02,11.03,8.012,16.020,25]pentacosa-1(17),2(11),3(8),4,6,12(16),20(25),21,23-nonaene-13,15-dione
• 英文别名: 5,23-dimethoxy-14-oxahexacyclo[15.8.0.02,11.03,8.012,16.020,25]pentacosa-1(17),2(11),3(8),4,6,12(16),20(25),21,23-nonaene-13,15-dione
• CAS: 1366018-28-1
• 化学式: C₂₆H₂₀O₅
• 分子量: 412.442
• InChiKey: SSNJXGHBXIBYDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,23-Dimethoxy-14-oxahexacyclo[15.8.0.02,11.03,8.012,16.020,25]pentacosa-1(17),2(11),3(8),4,6,12(16),20(25),21,23-nonaene-13,15-dione 在 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到2',3''-Dibrom-2'',3'-dimethoxy-1,2,7,8-tetrahydro-3,4:5,6-dibenzo-phenanthren-dicarbonsaeure-(9,10)-anhydrid
  参考文献：
  名称：

  基于四氢[5]螺旋烯的纳米粒子，用于依赖结构的细胞荧光成像

  摘要：

  设计并合成了四种具有四氢[5]螺旋结构的新型荧光染料，其特征是具有三基色发射色（蓝绿色红色），并通过NMR，MS和单晶X射线晶体学对其结构进行了表征。然后通过再沉淀法制备了基于荧光染料的有机纳米粒子，并对其光物理性质进行了研究。这些纳米粒子保留了有机染料的强发射性，并且还可以通过简单地调整三基色染料的比例来制备多色纳米粒子。这些有机纳米颗粒显示出低细胞毒性，良好的光稳定性和高量子产率。此外，纳米颗粒也可以应用于细胞荧光成像中。尤其，有趣的是，对于HeLa细胞，这些纳米颗粒从膜到细胞质的染色区域显示出明显的结构依赖性。该策略通过分子设计为活细胞的特定位置成像提供了荧光探针的新视角。

  DOI：

  10.1002/adfm.201400199

文献信息

• Tetrahydro[5]helicene-based imide dyes with intense fluorescence in both solution and solid state
  作者：Meng Li、Yingli Niu、Xiaozhang Zhu、Qian Peng、Hai-Yan Lu、Andong Xia、Chuan-Feng Chen

  DOI：10.1039/c3cc49680e

  日期：——

  Tetrahydro[5]helicene-based imide dyes with intense fluorescence and large Stokes shifts in solution and solid state were developed and theoretically investigated.

  开发了基于四氢[5]螺芳烃的亚酰亚胺染料，其在溶液和固态中具有强烈的荧光和大的斯托克斯位移，并进行了理论研究。
• Turn-On Fluorescent Sensor for Selective Detection of Zn²⁺, Cd²⁺, and Hg²⁺ in Water
  作者：Meng Li、Hai-Yan Lu、Rui-Li Liu、Jun-Dao Chen、Chuan-Feng Chen

  DOI：10.1021/jo3002744

  日期：2012.4.6

  A new fluorescent chemosensor based on a helical imide as fluorophore and a cyclen moiety as ionophore was synthesized, which not only showed enhanced fluorescent responses in the presence of Zn2+, Cd2+, and Hg2+ but also could simultaneously and selectively distinguish the three cations in a simulated physiological condition with the help of cysteine as an auxiliary reagent.
• A fluorescent probe based on tetrahydro[5]helicene derivative with large Stokes shift for rapid and highly selective recognition of hydrogen sulfide
  作者：Kun-Peng Wang、Qing-Lei Zhang、Xiang Wang、Yang Lei、Wen-Jun Zheng、Shaojin Chen、Qi Zhang、Hai-Yu Hu、Zhi-Qiang Hu

  DOI：10.1016/j.saa.2019.02.079

  日期：2019.5

  In this work, we have designed and synthesized a dinitrobenzene-sulfonate tetrahydro[5]helicene (H-DNP) as an effective fluorescent probe for detection of hydrogen sulfide (H2S). Upon the addition of H2S, a significant fluorescence enhancement (75-fold) at 495 nm can be observed with a distinct color change from colorless to yellow. Additionally, H-DNP shows low background spectroscopic signal, large Stokes Shift up to similar to 140 nm, good sensitivity, rapid response time less than 2 min, low detection limit (48 nM) and high selectivity toward common bio-thiols (Cysteine, Homocysteine and Glutathione). Compared with the previous dinitrophenoxy tetrahydro[5]helicene, this probe has shorter response time and lower detection limit. Most importantly, this probe H-DNP has low toxicity to cells and excellent cell permeability, which can be applied to visualize H2S in living cells. (C) 2019 Elsevier B.V. All rights reserved.