2-Bromo-9,10-dimethyl-9,10-dihydro-anthracene-9,10-diol | 103456-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-Bromo-9,10-dimethyl-9,10-dihydro-anthracene-9,10-diol
• 英文别名: 2-Bromo-9,10-dimethylanthracene-9,10-diol
• CAS: 103456-61-7
• 化学式: C₁₆H₁₅BrO₂
• 分子量: 319.198
• InChiKey: LNFBFUMJZJKFRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-9,10-dimethyl-9,10-dihydro-anthracene-9,10-diol 在 盐酸 、 正丁基锂 、 邻氨基苯甲酸 、 tin(ll) chloride 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.33h， 生成 2-(9,10-dihydro-9,10-dimethyl-9,10-<1',2'>-benzenoantracenyl) tert-butyl nitroxide
  参考文献：
  名称：

  9,10-Disubstituted-2-anthracenyl tert-butyl nitroxides. ESR spectroscopic indicators for singlet oxygen

  摘要：

  DOI：

  10.1021/jo00368a010
• 作为产物：
  描述：

  2-溴蒽醌 、 甲基锂 以 四氢呋喃 为溶剂， 生成 2-Bromo-9,10-dimethyl-9,10-dihydro-anthracene-9,10-diol
  参考文献：
  名称：

  Fluorescent probe, singlet oxygen detection agent, and singlet oxygen detection method

  摘要：

  本发明的目的是提供一种荧光探针，该探针可以轻松穿透细胞，并能够选择性和高效地检测在细胞中产生的单线态氧，以及含有该荧光探针的单线态氧检测剂和使用该荧光探针的单线态氧检测方法。用于检测单线态氧的荧光探针包括具有硅-罗丹明骨架和增强荧光探针在捕获单线态氧后的荧光强度大于捕获单线态氧前的荧光强度的骨架的化合物，或其盐、水合物或溶剂化物。

  公开号：

  US10564164B2

文献信息

• Far-Red Fluorescence Probe for Monitoring Singlet Oxygen during Photodynamic Therapy
  作者：Sooyeon Kim、Takashi Tachikawa、Mamoru Fujitsuka、Tetsuro Majima

  DOI：10.1021/ja504279r

  日期：2014.8.20

  Singlet oxygen ((1)O2), molecular oxygen in the lowest excited state, has a critical role in the cell-killing mechanism of photodynamic therapy (PDT). Although (1)O2 phosphorescence measurement has been mainly used to monitor (1)O2 formation during PDT, its intensity is far insufficient to obtain two-dimensional images of intracellular (1)O2 with the subcellular spatial resolution using the currently available near-IR detector. Here, we propose a new far-red fluorescence probe of (1)O2, namely, Si-DMA, composed of silicon-containing rhodamine and anthracene moieties as a chromophore and a (1)O2 reactive site, respectively. In the presence of (1)O2, fluorescence of Si-DMA increases 17 times due to endoperoxide formation at the anthracene moiety. With the advantage of negligible self-oxidation by photoirradiation (ΦΔ < 0.02) and selective mitochondrial localization, Si-DMA is particularly suitable for imaging (1)O2 during PDT. Among three different intracellular photosensitizers (Sens), Si-DMA could selectively detect the (1)O2 that is generated by 5-aminolevulinic acid-derived protoporphyrin IX, colocalized with Si-DMA in mitochondria. On the other hand, mitochondria-targeted KillerRed and lysosomal porphyrins could not induce fluorescence change of Si-DMA. This surprising selectivity of Si-DMA response depending on the Sens localization and photosensitization mechanism is caused by a limited intracellular (1)O2 diffusion distance (∼300 nm) and negligible generation of (1)O2 by type-I Sens, respectively. For the first time, we successfully visualized (1)O2 generated during PDT with a spatial resolution of a single mitochondrial tubule.
• KEANA J. F. W.; PRABHU VAIKUNTH S.; OHMIYA SHIGERU; KLOPFENSTEIN CH. E., J. ORG. CHEM., 51,(1986) N 18, 3456-3462
  作者：KEANA J. F. W.、 PRABHU VAIKUNTH S.、 OHMIYA SHIGERU、 KLOPFENSTEIN CH. E.

  DOI：——

  日期：——
• FLUORINE-CONTAINING AROMATIC COMPOUND AND PRODUCTION METHOD THEREOF
  申请人：Asahi Glass Company, Limited

  公开号：US20140357873A1

  公开（公告）日：2014-12-04

  A method of manufacturing a fluorine-containing aromatic compound represented by the following formula (2-1) or formula (2-2): R 1 is a linear perfluoroalkyl group having a carbon number of 1 to 3; X 2 to X 5 are a halogen atom or a hydrogen atom; R 2 to R 5 , L 1 and L 2 are a monovalent hydrocarbon group having a carbon number of 1 to 12, a monovalent aromatic hydrocarbon group, a monovalent hetero aromatic group, a halogen atom, or a hydrogen atom; one or more groups selected from R 2 to R 5 are a monovalent hydrocarbon group having a carbon number of 1 to 12, a monovalent aromatic hydrocarbon group, or a monovalent heteroaromatic group; and m is an integer of 0 or more, n is an integer of 1 or more, and m+n is an integer of 2 or more and 6 or less.
• Fluorescent Probe, Singlet Oxygen Detection Agent, and Singlet Oxygen Detection Method
  申请人：Osaka University

  公开号：US20170363636A1

  公开（公告）日：2017-12-21

  An object of the present invention is to provide a fluorescent probe that easily penetrates a cell and is capable of selectively and efficiently detecting singlet oxygen generated in the cell, a singlet oxygen detection agent containing the fluorescent probe, and a singlet oxygen detection method using the fluorescent probe. The fluorescent probe for detecting singlet oxygen comprises a compound having a silicon-rhodamine skeleton and a skeleton that increases the fluorescence of the fluorescent probe after trapping singlet oxygen to be greater than the fluorescence before trapping singlet oxygen, or a salt, hydrate, or solvate thereof.
• US9087996B2
  申请人：——

  公开号：US9087996B2

  公开（公告）日：2015-07-21