3-[4,6-Bis(3-carboxyphenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzoic acid | 859322-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[4,6-Bis(3-carboxyphenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzoic acid
• 英文别名: 3-[4,6-bis(3-carboxyphenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzoic acid
• CAS: 859322-94-4
• 化学式: C₂₁H₁₅B₃O₉
• 分子量: 443.778
• InChiKey: IUFSTCGUCGIWJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-[4,6-Bis(3-carboxyphenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzoic acid 、 N-(6-(dimethylamino)-9-(((trifluoromethyl)sulfonyl)oxy)-3H-thioxanthen-3-ylidene)-N-methylmethanaminium trifluoromethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 盐酸 、 溶剂黄146 作用下， 以 乙腈 、 水 为溶剂， 生成
  参考文献：
  名称：

  Novel Rhodamine Dyes via Suzuki Coupling of Xanthone Triflates with Arylboroxins

  摘要：

  新型罗丹明染料是通过“一锅法”从香豆素前体制备的，该方法涉及香豆素与三氟甲基磺酸酐反应，随后再进行钯介导的铃木耦合，将香豆素三氟甲基磺酸酯与芳基硼烷反应。通过该程序制备了9-(3-或4-羧基苯基)和9-(3-硝基苯基)取代的罗丹明。该方法同样适用于硫香豆素和硒香豆素，但不适用于碲香豆素。

  DOI：

  10.1055/s-0029-1218535
• 作为产物：
  描述：

  3-羧基苯硼酸 生成 3-[4,6-Bis(3-carboxyphenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzoic acid
  参考文献：
  名称：

  Novel Rhodamine Dyes via Suzuki Coupling of Xanthone Triflates with Arylboroxins

  摘要：

  新型罗丹明染料是通过“一锅法”从香豆素前体制备的，该方法涉及香豆素与三氟甲基磺酸酐反应，随后再进行钯介导的铃木耦合，将香豆素三氟甲基磺酸酯与芳基硼烷反应。通过该程序制备了9-(3-或4-羧基苯基)和9-(3-硝基苯基)取代的罗丹明。该方法同样适用于硫香豆素和硒香豆素，但不适用于碲香豆素。

  DOI：

  10.1055/s-0029-1218535

文献信息

• A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations
  作者：Thines Kanagasundaram、Antje Timmermann、Carsten S Kramer、Klaus Kopka

  DOI：10.3762/bjoc.15.250

  日期：——

  Background: Silicon rhodamines are of particular interest because of their advantageous dye properties (fluorescence- and biostability, quantum efficiency, tolerance to photobleaching). Therefore, silicon rhodamines find frequent application in STED (stimulated emission depletion) microscopy, as sensor molecules for, e.g., ions and as fluorophores for the optical imaging of tumors. Different strategies were already employed for their synthesis. Because of just three known literature examples in which Suzuki–Miyaura cross couplings gave access to silicon rhodamines in poor to moderate yields, we wanted to improve these first valuable experimental results.

  Results: The preparation of the xanthene triflate was enhanced and several boron sources were screened to find the optimal coupling partner. After optimization of the palladium catalyst, different substituted boroxines were assessed to explore the scope of the Pd-catalyzed cross-coupling reaction.

  Conclusions: A number of silicon rhodamines were synthesized under the optimized conditions in up to 91% yield without the necessity of HPLC purification. Moreover, silicon rhodamines functionalized with free acid moieties are directly accessible in contrast to previously described methods.

  背景：硅罗丹明因其有利的染料特性（荧光和生物稳定性、量子效率、对光漂白的耐受性）而特别受到关注。因此，硅罗丹明常用于STED（受激发射耗尽）显微镜，作为例如离子和肿瘤光学成像的荧光团的传感器分子。已经采用了不同的策略来合成它们。因为在仅有的三个已知文献实例中，铃木-宫浦交叉偶联以较差到中等产率得到了硅罗丹明，我们想要改进这些初步有价值的实验结果。 结果：提高了xanthene triflate的制备，并筛选了多种硼源以找到最佳的偶联伴侣。在优化了钯催化剂之后，评估了不同的取代硼氧烷来探索钯催化的交叉偶联反应的范围。 结论：在优化的条件下合成了多种硅罗丹明，产率高达91%，无需HPLC纯化。此外，与先前描述的方法相比，带有自由酸基团的功能化硅罗丹明可以直接获得。
• Novel Rhodamine Dyes via Suzuki Coupling of Xanthone Triflates with Arylboroxins
  作者：Michael Detty、Brandon Calitree

  DOI：10.1055/s-0029-1218535

  日期：2010.1

  Novel rhodamine dyes were prepared from xanthone precursors in a ‘one-pot’ procedure via reaction of the xanthone with trifluoromethanesulfonic anhydride followed by Pd-mediated Suzuki coupling between the xanthone triflate and an arylboroxin. Rhodamines with 9-(3- or 4-carboxyphenyl) and 9-(3-nitrophenyl) substituents were prepared by this procedure. The procedure also works well with thio- and selenoxanthones, but not with telluroxanthones.

  新型罗丹明染料是通过“一锅法”从香豆素前体制备的，该方法涉及香豆素与三氟甲基磺酸酐反应，随后再进行钯介导的铃木耦合，将香豆素三氟甲基磺酸酯与芳基硼烷反应。通过该程序制备了9-(3-或4-羧基苯基)和9-(3-硝基苯基)取代的罗丹明。该方法同样适用于硫香豆素和硒香豆素，但不适用于碲香豆素。