N,N,N',N'-tetramethyl-spiro[benzo[c]thiophene-1(3H),9'-[9H]xanthene]-3',6'-diamine | 943219-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N,N,N',N'-tetramethyl-spiro[benzo[c]thiophene-1(3H),9'-[9H]xanthene]-3',6'-diamine
• 英文别名: 3-N',3-N',6-N',6-N'-tetramethylspiro[1H-2-benzothiophene-3,9'-xanthene]-3',6'-diamine
• CAS: 943219-53-2
• 化学式: C₂₄H₂₄N₂OS
• 分子量: 388.533
• InChiKey: PMAFREYRXRIDIY-UHFFFAOYSA-N

物化性质

• 沸点：
  569.8±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N,N',N'-tetramethyl-spiro[benzo[c]thiophene-1(3H),9'-[9H]xanthene]-3',6'-diamine 在 sodium hypochlorite 作用下， 以 phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 以23%的产率得到9-(2-sulfoxymethylphenyl)-3,6-bis(dimethylamino)xanthylium
  参考文献：
  名称：

  Development of a Highly Specific Rhodamine-Based Fluorescence Probe for Hypochlorous Acid and Its Application to Real-Time Imaging of Phagocytosis

  摘要：

  The tetramethylrhodamine (TMR) fluorophore is a useful platform for fluorescence probes, being applicable, for example, to biological investigations utilizing fluorescence microscopy, owing to its excellent photochemical properties in aqueous media. We have developed new TMR derivatives that show different dependences of their behavior upon the environment. Among them, HMTMR showed unique characteristics, and its putative spirocyclic structure was confirmed by X-ray crystallography. Utilizing this discovery, we have established a strategy to modulate the fluorescence of TMR by regulating the spirocyclization, and we have obtained a new fluorescence probe that can detect hypochlorous acid specifically. This probe, HySOx, can work in 99.9% aqueous solution at pH 7.4 and was confirmed to be able to detect hypochlorous acid being generated inside phagosomes in real time. HySOx is tolerant to autoxidation and photobleaching under bioimaging conditions. Regulation of the spirocyclization of rhodamines, as we describe here, provides a new approach to the rational development of novel fluorescence probes.

  DOI：

  10.1021/ja068740g
• 作为产物：
  描述：

  焦宁Y 在 potassium cyanide 、 叔丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 正戊烷 为溶剂， 反应 60.17h， 生成 N,N,N',N'-tetramethyl-spiro[benzo[c]thiophene-1(3H),9'-[9H]xanthene]-3',6'-diamine
  参考文献：
  名称：

  Development of a Highly Specific Rhodamine-Based Fluorescence Probe for Hypochlorous Acid and Its Application to Real-Time Imaging of Phagocytosis

  摘要：

  The tetramethylrhodamine (TMR) fluorophore is a useful platform for fluorescence probes, being applicable, for example, to biological investigations utilizing fluorescence microscopy, owing to its excellent photochemical properties in aqueous media. We have developed new TMR derivatives that show different dependences of their behavior upon the environment. Among them, HMTMR showed unique characteristics, and its putative spirocyclic structure was confirmed by X-ray crystallography. Utilizing this discovery, we have established a strategy to modulate the fluorescence of TMR by regulating the spirocyclization, and we have obtained a new fluorescence probe that can detect hypochlorous acid specifically. This probe, HySOx, can work in 99.9% aqueous solution at pH 7.4 and was confirmed to be able to detect hypochlorous acid being generated inside phagosomes in real time. HySOx is tolerant to autoxidation and photobleaching under bioimaging conditions. Regulation of the spirocyclization of rhodamines, as we describe here, provides a new approach to the rational development of novel fluorescence probes.

  DOI：

  10.1021/ja068740g

文献信息

• FLUORESCENT PROBE
  申请人：Nagano Tetsuo

  公开号：US20090317914A1

  公开（公告）日：2009-12-24

  A compound represented by the following general formula (I): [R 1 represents hydrogen atom, or 1 to 4 monovalent substituents; R 2 , R 4 , R 5 , and R 7 represent hydrogen atom, or a monovalent substituent; R 3 represents ═O or ═N + (R 8 )(R 9 ).M − (R 8 and R 9 represent an alkyl group, and M − represents a counter ion); R 6 represents —OH or —N(R 10 )(R 11 ) (R 10 and R 11 represent an alkyl group); n represents an integer of 1 to 3; and X represents —SH or —OH], which is useful for selective measurement of hypochlorite ion and the like.
• LONG-AFTERGLOW LUMINESCENT MATERIAL
  申请人：FUDAN UNIVERSITY

  公开号：US20220204838A1

  公开（公告）日：2022-06-30

  Disclosed is a long-afterglow luminescent material, comprising A) at least one light-absorbing agent, B) at least one luminescent agent, and C) at least one photochemical cache agent. The light-absorbing agent and the luminescent agent are compounds having different structures, and the cache agent is selected from one or more compounds of formula (I), (II) and/or (III). The material has luminescent intensity reaching the level of commercialized inorganic long-afterglow powder SrAl 2 O 4 :Eu 2+ , Dy 3+ , and can emit light when the exciting light is turned off with a light emitting time up to 100 ms to 3600 s.
• US8143069B2
  申请人：——

  公开号：US8143069B2

  公开（公告）日：2012-03-27
• Development of a Highly Specific Rhodamine-Based Fluorescence Probe for Hypochlorous Acid and Its Application to Real-Time Imaging of Phagocytosis
  作者：Suguru Kenmoku、Yasuteru Urano、Hirotatsu Kojima、Tetsuo Nagano

  DOI：10.1021/ja068740g

  日期：2007.6.13

  The tetramethylrhodamine (TMR) fluorophore is a useful platform for fluorescence probes, being applicable, for example, to biological investigations utilizing fluorescence microscopy, owing to its excellent photochemical properties in aqueous media. We have developed new TMR derivatives that show different dependences of their behavior upon the environment. Among them, HMTMR showed unique characteristics, and its putative spirocyclic structure was confirmed by X-ray crystallography. Utilizing this discovery, we have established a strategy to modulate the fluorescence of TMR by regulating the spirocyclization, and we have obtained a new fluorescence probe that can detect hypochlorous acid specifically. This probe, HySOx, can work in 99.9% aqueous solution at pH 7.4 and was confirmed to be able to detect hypochlorous acid being generated inside phagosomes in real time. HySOx is tolerant to autoxidation and photobleaching under bioimaging conditions. Regulation of the spirocyclization of rhodamines, as we describe here, provides a new approach to the rational development of novel fluorescence probes.