4-羧基宾夕法尼亚绿甲酯 | 879288-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 4-羧基宾夕法尼亚绿甲酯
• 英文名称: 4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzoic acid methyl ester
• 英文别名: methyl 4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzoate；4-carboxy-Pennsylvania Green methyl ester；4-carboxy-pennsylvania green methyl wster；methyl 4-(2,7-difluoro-3-hydroxy-6-oxoxanthen-9-yl)-3-methylbenzoate
• CAS: 879288-18-3
• 化学式: C₂₂H₁₄F₂O₅
• 分子量: 396.347
• InChiKey: DPZLMQCYZDHMGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  220-224 °C
• 沸点：
  595.3±50.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-羧基宾夕法尼亚绿甲酯 在 氢氧化钾 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.0h， 生成 N-(4-{[(2-amino-9H-purin-6-yl)oxy]methyl}benzyl)-4-(2,7-difluoro-3,6-dihydroxy-xanthen-9H-yl)-3-methylbenzamide
  参考文献：
  名称：

  A Concise Synthesis of the Pennsylvania Green Fluorophore and Labeling of Intracellular Targets with O⁶-Benzylguanine Derivatives

  摘要：

  We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O-6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O-6-benzyiguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.

  DOI：

  10.1021/ol7015093
• 作为产物：
  描述：

  4-氟间苯二酚 在 甲烷磺酸 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 30.0h， 生成 4-羧基宾夕法尼亚绿甲酯
  参考文献：
  名称：

  A Concise Synthesis of the Pennsylvania Green Fluorophore and Labeling of Intracellular Targets with O⁶-Benzylguanine Derivatives

  摘要：

  We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O-6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O-6-benzyiguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.

  DOI：

  10.1021/ol7015093

文献信息

• Efficient and Scalable Synthesis of 4-Carboxy-Pennsylvania Green Methyl Ester: A Hydrophobic Building Block for Fluorescent Molecular Probes
  作者：Blake Peterson、Zachary Woydziak、Liqiang Fu

  DOI：10.1055/s-0033-1338535

  日期：——

  practical synthesis of 4-carboxy-Pennsylvania Green methyl ester. Derivatives of this hydrophobic fluorinated fluorophore, a hybrid of the dyes Oregon Green and Tokyo Green, are often cell-permeable, enabling labeling of intracellular targets and components. Moreover, the low pK a of Pennsylvania Green (4.8) confers bright fluorescence in acidic cellular compartments, such as endosomes, enhancing its utility

  摘要 氟化荧光团是研究生物系统的宝贵工具。然而，这些化合物的胺反应性单一异构体衍生物通常非常昂贵。为了提供廉价的替代品，我们开发了 4-羧基-宾夕法尼亚绿甲酯的实用合成方法。这种疏水性氟化荧光团的衍生物是俄勒冈绿和东京绿染料的混合物，通常具有细胞渗透性，能够标记细胞内的靶标和成分。此外，低 p K a宾夕法尼亚格林 (4.8) 的研究在酸性细胞区室（例如内体）中赋予明亮的荧光，从而增强其在化学生物学研究中的实用性。为了改善对关键中间体 2,7-difluoro-3,6-dihydroxyxanthen-9-one 的获取，我们对双（2,4,5-三氟苯基）甲酮进行了超过 40 克规模的氢氧化物的迭代亲核芳族取代. 关键中间体用于制备超过 15 克纯 4-羧基-宾夕法尼亚绿甲酯，总产率为 28%，无需使用色谱法。该化合物可以以基本定量的产率转化为胺反应性N-羟基琥珀酰亚胺酯，用于合成多种荧光分子探针。
• The Pennsylvania Green Fluorophore: A Hybrid of Oregon Green and Tokyo Green for the Construction of Hydrophobic and pH-Insensitive Molecular Probes
  作者：Laurie F. Mottram、Siwarutt Boonyarattanakalin、Rebecca E. Kovel、Blake R. Peterson

  DOI：10.1021/ol052655g

  日期：2006.2.1

  Fluorescent small molecules are powerful tools for exploring cellular biology. As a more hydrophobic, photostable, and less pH-sensitive alternative to fluorescein, we synthesized Pennsylvania Green, a bright, monoanionic fluorophore related to Oregon Green and Tokyo Green. Comparison of membrane probes comprising N-alkyl-3 beta-cholesterylamine linked to 4-carboxy-Tokyo Green (pK(a) similar to 6.2) and 4-carboxy-Pennsylvania Green (pK(a) similar to 4.8) revealed that only Pennsylvania Green was highly fluorescent in acidic early and recycling endosomes within living mammalian cells.
• A Concise Synthesis of the Pennsylvania Green Fluorophore and Labeling of Intracellular Targets with <i>O</i><i>⁶</i>-Benzylguanine Derivatives
  作者：Laurie F. Mottram、Ewa Maddox、Markus Schwab、Florent Beaufils、Blake R. Peterson

  DOI：10.1021/ol7015093

  日期：2007.9.1

  We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O-6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O-6-benzyiguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.