2,7-dichloro-3,6-dihydroxyxanth-9-one | 91821-41-9

• 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: 2,7-dichloro-3,6-dihydroxyxanth-9-one
• 英文别名: 2,7-dichloro-3,6-dihydroxy-xanthen-9-one；2,7-Dichlor-3,6-dihydroxy-xanthon；2,7-Dichloro-3,6-dihydroxy-9H-xanthen-9-one；2,7-dichloro-3,6-dihydroxyxanthen-9-one
• CAS: 91821-41-9
• 化学式: C₁₃H₆Cl₂O₄
• 分子量: 297.094
• InChiKey: ZDXVNXSGKAXUPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-dichloro-3,6-dihydroxyxanth-9-one 在 咪唑 、 叔丁基锂 作用下， 以 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 2.5h， 生成 2,7-Dichloro-6-hydroxy-9-(18-methyl-2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)xanthen-3-one
  参考文献：
  名称：

  Rational design of novel photoinduced electron transfer type fluorescent probes for sodium cation

  摘要：

  We have developed novel fluorescence probes for sodium cation based on photoinduced electron transfer (PeT). In this study, we rationally designed new probes and succeeded in achieving fluorescence enhancement upon sodium ion binding by reducing the HOMO energy level of the chelator group within the probe molecule. Our new probes show low pH dependency, possibly because of their simple structures. Our results confirm the value of rational probe design based on PeT. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.108
• 作为产物：
  描述：

  4-氯间苯二酚 在 zinc(II) chloride 、 三氯氧磷 作用下， 以 水 为溶剂， 20.0~220.0 ℃ 、253.31 kPa 条件下， 反应 12.0h， 生成 2,7-dichloro-3,6-dihydroxyxanth-9-one
  参考文献：
  名称：

  Rational design of novel photoinduced electron transfer type fluorescent probes for sodium cation

  摘要：

  We have developed novel fluorescence probes for sodium cation based on photoinduced electron transfer (PeT). In this study, we rationally designed new probes and succeeded in achieving fluorescence enhancement upon sodium ion binding by reducing the HOMO energy level of the chelator group within the probe molecule. Our new probes show low pH dependency, possibly because of their simple structures. Our results confirm the value of rational probe design based on PeT. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.108

文献信息

• Fluorescent probe
  申请人：——

  公开号：US07524974B2

  公开（公告）日：2009-04-28

  A fluorescent probe which is represented by the following formula (I): (wherein, R1 and R2 represent hydrogen atom, or a substituent for trapping proton, a metal ion, or an active oxygen species, or the like; R3 represents a monovalent substituent; R4 and R5 represent hydrogen atom or a halogen atom; R6 represents hydrogen atom, an alkylcarbonyl group, or an alkylcarbonyloxymethyl group, provided that a combination of R1, R2, and R3 provides (1) substantially high electron density of the benzene ring to which said groups bind, so that the compound represented by the formula (I) is substantially no fluorescent before the trapping of proton, or the like, and (2) substantially reduced electron density of the benzene ring to which said groups bind, so that a compound after the trapping, which is derived from the compound represented by the formula (I) is substantially highly fluorescent after the trapping of proton or the like). A fluorescent probe having an excellent fluorescence property is provided.

  一种荧光探针，其由以下公式（I）表示： （其中，R1和R2代表氢原子，或用于捕获质子、金属离子或活性氧物种等的取代基；R3代表一价取代基；R4和R5代表氢原子或卤素原子；R6代表氢原子、烷基羰基基团或烷基羰氧甲基基团，前提是R1、R2和R3的组合提供（1）苯环的电子密度显著高，使得由公式（I）表示的化合物在捕获质子等之前基本不发光，以及（2）苯环的电子密度显著降低，使得捕获后的化合物，即由公式（I）表示的化合物衍生物，在捕获质子等后基本上具有高荧光性）。提供了具有优异荧光性能的荧光探针。
• Visible wavelength fluorescent calcium indicators that are (i) leakage resistant and (ii) operate near membranes
  申请人：Minta Akwasi

  公开号：US20050233467A1

  公开（公告）日：2005-10-20

  A new class of visible wavelength fluorescent calcium indicators with the BAPTA-like portion rendered zwitterionic by introduction of amine and carboxylic groups. “Fluo” compounds generally function with no extra ionized groups. The modified BAPTA moiety confers new properties while retaining ion selectivity and pH insensitivity. The dyes demonstrate reduced cell leakage and improved ability to study calcium near the cell membrane and preserve the fluorescent properties of “fluo” dyes. The modifications include (a) piperazinoacetic acid XIII for the leakage resistance (FLUO-LR), (b) dodecylpiperazine XIII for a near membrane indicator (FLUO-MOMO, FLUO-NOMO amphipathic “fluo” indicators which bind to cellular membranes and respond to calcium near the membrane), and (c) a propionic acid XII for general leakage resistance -FLUO-LOJO, FLUO-KOJO “fluo” indicators with an extra charge that enables them to resist leakage).

  一种新的可见光荧光钙指示剂，其BAPTA类部分通过引入胺和羧基使其带有两性离子。 "Fluo"化合物通常不需要额外的离子化基团。修改后的BAPTA基团保留了离子选择性和pH不敏感性的同时赋予了新的性质。这些染料表现出降低的细胞泄漏和改善了研究细胞膜附近钙离子的能力以及保持“fluo”染料的荧光特性。这些修改包括（a）对偶氮基乙酸XIII用于防泄漏（FLUO-LR），（b）十二烷基哌嗪XIII用于近膜指示剂（FLUO-MOMO，FLUO-NOMO两性“fluo”指示剂，它们结合到细胞膜并对膜附近的钙离子做出反应），以及（c）丙酸XII用于一般的防泄漏-FLUO-LOJO，FLUO-KOJO“fluo”指示剂带有额外的电荷，使它们能够抵抗泄漏。
• Fluorescent indicator dyes for calcium working at long wavelengths
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0314480A2

  公开（公告）日：1989-05-03

  A new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths combine at least one tricyclic chromophore with a tetracarboxylate parent CA2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA2+] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.

  一类具有可见激发和发射波长的新型钙特异性荧光指示剂染料将至少一种三环发色团与四羧酸母体 CA2+ 螯合化合物结合在一起，该化合物具有 BAPTA 特有的八配位配位基团模式，从而产生类似罗丹明或荧光素的荧光团。钙2+的结合可使新化合物的荧光增加 40 倍。钙2+的解离常数在 0.37-2.3 微摩尔范围内，因此新指示剂对高浓度[CA2+]的分辨能力比以前的前代化合物（如 quin-2 或 fluo-2）更强。与以前的指示剂所需的紫外波长相比，新化合物的可见光激发波长更便于荧光显微镜和流式细胞仪的使用。
• US5049673A
  申请人：——

  公开号：US5049673A

  公开（公告）日：1991-09-17
• Rational design of novel photoinduced electron transfer type fluorescent probes for sodium cation
  作者：Suguru Kenmoku、Yasuteru Urano、Koujirou Kanda、Hirotatsu Kojima、Kazuya Kikuchi、Tetuso Nagano

  DOI：10.1016/j.tet.2004.06.108

  日期：2004.11

  We have developed novel fluorescence probes for sodium cation based on photoinduced electron transfer (PeT). In this study, we rationally designed new probes and succeeded in achieving fluorescence enhancement upon sodium ion binding by reducing the HOMO energy level of the chelator group within the probe molecule. Our new probes show low pH dependency, possibly because of their simple structures. Our results confirm the value of rational probe design based on PeT. (C) 2004 Elsevier Ltd. All rights reserved.