3,8-dihydroxy-spiro[benzo[b]xanthene-12,1'-phthalan]-3'-one

• 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: 3,8-dihydroxy-spiro[benzo[b]xanthene-12,1'-phthalan]-3'-one
• 英文别名: 3,8-Dihydroxy-spiro[benzo[b]xanthen-12,1'-phthalan]-3'-on；3',8'-Dihydroxyspiro[2-benzofuran-3,12'-benzo[b]xanthene]-1-one
• 化学式: C₂₄H₁₄O₅
• 分子量: 382.372
• InChiKey: HXPXKJLFRLWYMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-bromonaphthalene-2,7-diol 在 盐酸 、 正丁基锂 、 甲烷磺酸 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 13.5h， 生成 3,8-dihydroxy-spiro[benzo[b]xanthene-12,1'-phthalan]-3'-one
  参考文献：
  名称：

  Exhaustive Syntheses of Naphthofluoresceins and Their Functions

  摘要：

  Naphthofluorescein and/or seminaphthofluorescein derivatives possessing the additional benzene units to one or both sides of fluorescein were exhaustively constructed through Friedel-Crafts type reactions between corresponding aroylbenzoic acids and dihydroxynaphthalenes. Compound 4 works as a one-dye pH indicator, which shows red in strong acid condition and blue in basic solution. Compound 23 (diacetate of compound 4) shows good transitivity to the HEK 293 cells and acts as a fluorescent pigment for the living cell imaging. Compounds 5, 6, and 9 show fluorescent emission in the NIR region (>700 nm) and imply the potentialities of NIR fluorescent probes.

  DOI：

  10.1021/jo300177b

文献信息

• ANALYTE DETECTION USING NEAR-INFRARED FLUOROPHORES
  申请人：Portland State University

  公开号：US20160223558A1

  公开（公告）日：2016-08-04

  Embodiments of compounds for selectively detecting an analyte are disclosed, along with methods and kits for detecting analytes with the compounds. The compounds are bridged viologen conjugates including at least one fluorophore according to the general structure At least one of R 1 /R 2 , R 2 /R 3 , R 3 /R 4 , R 5 /R 6 , R 6 /R 7 , and/or R 7 /R 8 together form a substituted or unsubstituted cycloalkyl or aryl.

  公开了用于选择性检测分析物的化合物实施例，以及使用这些化合物检测分析物的方法和试剂盒。这些化合物是包括至少一种荧光团的桥联紫罗兰类化合物，其一般结构如下：至少有R1/R2、R2/R3、R3/R4、R5/R6、R6/R7和/或R7/R8中的至少一对形成取代或未取代的环烷基或芳基。
• Ghatak; Dutt, Journal of the Indian Chemical Society, 1929, vol. 6, p. 468
  作者：Ghatak、Dutt

  DOI：——

  日期：——
• Exhaustive Syntheses of Naphthofluoresceins and Their Functions
  作者：Eriko Azuma、Naoko Nakamura、Kouji Kuramochi、Takahiro Sasamori、Norihiro Tokitoh、Ikuko Sagami、Kazunori Tsubaki

  DOI：10.1021/jo300177b

  日期：2012.4.6

  Naphthofluorescein and/or seminaphthofluorescein derivatives possessing the additional benzene units to one or both sides of fluorescein were exhaustively constructed through Friedel-Crafts type reactions between corresponding aroylbenzoic acids and dihydroxynaphthalenes. Compound 4 works as a one-dye pH indicator, which shows red in strong acid condition and blue in basic solution. Compound 23 (diacetate of compound 4) shows good transitivity to the HEK 293 cells and acts as a fluorescent pigment for the living cell imaging. Compounds 5, 6, and 9 show fluorescent emission in the NIR region (>700 nm) and imply the potentialities of NIR fluorescent probes.