3-(7-methoxy-6-(4-nitrophenylazo)-3,4-dihydro-2H-quinolin-1-yl)propane-1-sulfonic acid | 1345614-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(7-methoxy-6-(4-nitrophenylazo)-3,4-dihydro-2H-quinolin-1-yl)propane-1-sulfonic acid
• 英文别名: 3-[7-methoxy-6-(4-nitrophenylazo)-3,4-dihydro-2H-quinolin-1-yl]propane-1-sulfonic acid
• CAS: 1345614-66-5
• 化学式: C₁₉H₂₂N₄O₆S
• 分子量: 434.473
• InChiKey: IFQOPZBCTKUZBQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  134.7
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-乙基-1,2,3,4-四氢喹啉-7-醇 、 3-(7-methoxy-6-(4-nitrophenylazo)-3,4-dihydro-2H-quinolin-1-yl)propane-1-sulfonic acid 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 1-ethyl-11-(3-sulfopropyl)-3,4,8,9,10,11-hexahydro-2H-13-oxa-6,11-diaza-1-azonia-pentacene trifluoroacetate
  参考文献：
  名称：

  Synthesis of Near-IR Fluorescent Oxazine Dyes with Esterase-Labile Sulfonate Esters

  摘要：

  Near-IR oxazine dyes are reported that contain sulfonate esters which are rapidly cleaved by esterase activity to unmask highly polar anionic sulfonates. Strategies for the synthesis of these dyes included the development of milder dye condensation conditions with Improved functional compatibility and the use of an alkyl halide that allows for the Introduction of esterase-labile sulfonates without the need for sulfonation of the target molecule.

  DOI：

  10.1021/ol202619f
• 作为产物：
  描述：

  3,4-二氢-7-羟基-2(1H)-喹啉酮 在 硼烷四氢呋喃络合物 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-(7-methoxy-6-(4-nitrophenylazo)-3,4-dihydro-2H-quinolin-1-yl)propane-1-sulfonic acid
  参考文献：
  名称：

  Synthesis of Near-IR Fluorescent Oxazine Dyes with Esterase-Labile Sulfonate Esters

  摘要：

  Near-IR oxazine dyes are reported that contain sulfonate esters which are rapidly cleaved by esterase activity to unmask highly polar anionic sulfonates. Strategies for the synthesis of these dyes included the development of milder dye condensation conditions with Improved functional compatibility and the use of an alkyl halide that allows for the Introduction of esterase-labile sulfonates without the need for sulfonation of the target molecule.

  DOI：

  10.1021/ol202619f

文献信息

• A Trifluoroacetic Acid-labile Sulfonate Protecting Group and Its Use in the Synthesis of a Near-IR Fluorophore
  作者：Steven M. Pauff、Stephen C. Miller

  DOI：10.1021/jo302065u

  日期：2013.1.18

  Sulfonated molecules exhibit high water solubility, a property that is valuable for many biological applications but often complicates their synthesis and purification. Here we report a sulfonate protecting group that is resistant to nucleophilic attack but readily removed with trifluoroacetic acid (TFA). The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and

  磺化分子表现出高水溶性，这一特性对许多生物应用很有价值，但通常会使它们的合成和纯化复杂化。在这里，我们报告了一种磺酸盐保护基团，它可以抵抗亲核攻击，但很容易用三氟乙酸 (TFA) 去除。这种保护基团的使用改进了磺化近红外荧光团的合成，温和的脱保护条件允许在不需要色谱法的情况下分离产物。