2-(3-hydroxy-6-methoxy-9H-xanthen-9-yl)benzoic acid methyl ester | 1374021-44-9

• 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-(3-hydroxy-6-methoxy-9H-xanthen-9-yl)benzoic acid methyl ester
• 英文别名: 2-(3-hydroxy-6-methoxy-9H-xanthene-9-yl)benzoic acid methyl ester；methyl 2-(3-hydroxy-6-methoxy-9H-xanthen-9-yl)benzoate
• CAS: 1374021-44-9
• 化学式: C₂₂H₁₈O₅
• 分子量: 362.382
• InChiKey: ASLRTXMZCGAXON-UHFFFAOYSA-N

物化性质

• 沸点：
  503.4±50.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷；甲醇；二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxy-6-methoxy-9H-xanthen-9-yl)benzoic acid methyl ester 在 甲酸 、 copper(II) nitrate trihydrate 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 7.5h， 生成 methyl 2-(6-methoxy-3-oxo-3H-xanthen-9-yl)benzoate
  参考文献：
  名称：

  A Highly Selective Fluorescence “Turn-On” Probe for Cu(II) Based on Reaction and Its Imaging in Living Cells

  摘要：

  A new oxidative C-O bond cleavage reaction-based probe FluHMPP was designed and prepared. FluHMPP displays excellent selective turn-on fluorescence response for Cu-II in aqueous solution under visible light excitation. The cleavage products are fully characterized. Fluorescein fragment is further oxidized to highly fluorescent MFME (3'-O-methylfluorescein methyl ester), and benzyl ether of imine fragment has been transformed to carboxyl. Confocal microscopy experiments have demonstrated that FluHMPP could also be used in live cells for the detection of Cu-II.

  DOI：

  10.1021/ic401865e
• 作为产物：
  描述：

  fluorescein free acid 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 2-(3-hydroxy-6-methoxy-9H-xanthen-9-yl)benzoic acid methyl ester
  参考文献：
  名称：

  细胞内硫醇和光照明顺序激活双锁定分子探针，以精确的空间精度长期显示和跟踪细胞

  摘要：

  合成了一种新型的可光转换的荧光探针，该探针可以被细胞内的硫醇激活。这种分子探针包括三部分：7-氨基香豆素光触发，可去除硫醇的能量受体，以及具有作为荧光报告分子的细胞内硫醇反应性的笼状荧光素支架。在细胞外，能量受体阻断香豆素的发射，该香豆素调节荧光素的光裂解和光活化。在细胞内，高浓度的硫醇释放出能量受体，从而激活了光触发的S1状态，该光触发了香豆素蓝色荧光以进行预可视化，并释放了笼状的绿色荧光素，从而在照明时突出了特定的细胞。与传统的光活化有机染料相比，细胞内硫醇激活的探针需要双重激活：一种是细胞内硫醇激活，另一种是光激活。双重激活将荧光精确地限制在活细胞内部以及光激活的特定空间区域，因此在活细胞中具有精确的空间精度。

  DOI：

  10.1002/chem.201403905

文献信息

• Fluorescence turn-on detection of hypochlorous acid via HOCl-promoted dihydrofluorescein-ether oxidation and its application in vivo
  作者：Yi Zhou、Ju-Ying Li、Kai-Hui Chu、Ke Liu、Cheng Yao、Jing-Yun Li

  DOI：10.1039/c2cc30265a

  日期：——

  We report three new water-soluble dihydrofluorescein-ether probes FCN1, FCN2 and FCN3 for the detection of hypochlorous acid (HOCl), which were designed on the basis of a specific HOCl-promoted oxidation reaction. This work also provided a useful method to monitor the accumulated HOCl in specific organelles using a zebrafish model.

  我们报告了三种新型水溶性二氟荧光素醚探针 FCN1、FCN2 和 FCN3，用于检测亚氯酸（HOCl），这些探针是基于特定的 HOCl 促进氧化反应设计的。本研究还提供了一种有用的方法，通过斑马鱼模型监测特定细胞器中累积的 HOCl。
• Development of Highly Sensitive Fluorescent Probes for Detection of Intracellular Copper(I) in Living Systems
  作者：Masayasu Taki、Shohei Iyoshi、Akio Ojida、Itaru Hamachi、Yukio Yamamoto

  DOI：10.1021/ja100714p

  日期：2010.5.5

  fluorescent probes FluTPA1 and FluTPA2, in which the tetradentate ligand tris[(2-pyridyl)methyl]amine (TPA) is connected to a reduced form of a fluorescein platform through a benzyl ether linkage. These probes selectively react with copper ions in the presence of submillimolar glutathione and emit intense green fluorescence from the reaction product, O-methylfluorescein. Confocal images of live cells further

  我们在这里描述了新的铜选择性荧光探针 FluTPA1 和 FluTPA2，其中四齿配体三 [(2-吡啶基) 甲基] 胺 (TPA) 通过苄基醚键连接到荧光素平台的还原形式。这些探针在亚毫摩尔谷胱甘肽存在下选择性地与铜离子反应，并从反应产物 O-甲基荧光素发出强烈的绿色荧光。活细胞的共聚焦图像进一步表明 FluTPA2 具有膜渗透性，并且可以观察活细胞中存在的 Cu(I)。
• Fluorescent probes for detecting monoamine oxidase activity and cell imaging
  作者：Xuefeng Li、Huatang Zhang、Yusheng Xie、Yi Hu、Hongyan Sun、Qing Zhu

  DOI：10.1039/c3ob42326c

  日期：——

  A series of new fluorogenic probes for monoamine oxidases (MAOs) were reported based on an oxidation and β-elimination mechanism. The limits of detection of the probes for MAO-A and -B were determined to be 3.5 and 6.0 μg mL−1 respectively. These probes displayed strong activity towards MAOs, especially MAO-B. Cellular imaging studies were also successfully conducted with MCF-7 cells.

  根据氧化和β-消除机制，报告了一系列新的单胺氧化酶（MAOs）荧光探针。这些探针对 MAO-A 和 -B 的检测限分别为 3.5 和 6.0 μg mL-1。这些探针对 MAOs（尤其是 MAO-B）具有很强的活性。此外，还用 MCF-7 细胞成功地进行了细胞成像研究。
• Development of Green-Emitting Iron Complex-Based Fluorescent Probes for Intracellular Hydrogen Peroxide Imaging
  作者：Yutaka Hitomi、Toshiyuki Takeyasu、Masahito Kodera

  DOI：10.1246/bcsj.20140055

  日期：2014.7.15

  We previously reported the synthesis of the metal-based fluorescent probes MBFh1 and MBFh2 for hydrogen peroxide (H2O2) imaging, which release the red-emitting fluorophore resorufin, whose response rate is significantly faster than that of other nonmetal-based H2O2 probes, upon reacting with H2O2. In this study, we have synthesized the new fluorescent probe MBFh3 1 and its ester derivatives 2 and 3, in which a mononuclear nonheme iron(III)–monoamido complex and a 3′-O-methyldihydrofluorescein derivative are connected via a propane linker. Probes 2 and 3 are methyl and 1-(ethoxycarbonyloxy)ethyl ester derivatives of 1, respectively. These probes rapidly react with H2O2 to release green-emitting 3′-O-methylfluoresceins. Fluorescent microscopy studies using HeLa and A431 cells showed that intracellular H2O2 can be visualized using probes 1 and 2, but not 3.

  我们以前曾报道过用于过氧化氢（H2O2）成像的金属基荧光探针 MBFh1 和 MBFh2 的合成，它们与 H2O2 反应后释放出红色发光荧光团 resorufin，其响应速度明显快于其他非金属基 H2O2 探针。在这项研究中，我们合成了新的荧光探针 MBFh3 1 及其酯衍生物 2 和 3，其中单核非血红素铁（III）-单氨基配合物和 3′-O-甲基二氢荧光素衍生物通过丙烷连接。探针 2 和 3 分别是 1 的甲基和 1-（乙氧基羰基氧基）乙基酯衍生物。这些探针能迅速与 H2O2 反应，释放出绿色发光的 3′-O-甲基荧光素。使用 HeLa 和 A431 细胞进行的荧光显微镜研究表明，使用探针 1 和 2 可以观察到细胞内的 H2O2，而使用探针 3 则不能。
• Rational Utilization of Black Phosphorus Nanosheets to Enhance Palladium‐Mediated Bioorthogonal Catalytic Activity for Activation of Therapeutics
  作者：Mingjie Rong、Jian Liu、Zhen Sun、Tong Li、Yang Li、Chunhuan Jiang、Lehui Lu

  DOI：10.1002/anie.202216822

  日期：——

  A novel strategy is applied to enhance palladium-mediated bioorthogonal catalytic activity by using a powerful partner: black phosphorus (BP) nanosheets, which can accelerate the transformation of Pd2+ to Pd0 to boost the reaction cycle, thus achieving a superior decaging efficiency of prodyes and prodrugs.

  一种新策略通过使用强大的合作伙伴黑磷 (BP) 纳米片来增强钯介导的生物正交催化活性，它可以加速 Pd 2+向 Pd 0的转化以促进反应循环，从而实现卓越的降解效率prodyes 和 prodrugs。