3-oxo-3H-phenoxazin-7-yl isobutyrate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-oxo-3H-phenoxazin-7-yl isobutyrate
• 英文别名: isobutyryl resorufin；(7-Oxophenoxazin-3-yl) 2-methylpropanoate
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: WUFVPNUJTQNLHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二氟甲烷亚磺酸钠 、 3-oxo-3H-phenoxazin-7-yl isobutyrate 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以88%的产率得到2-((difluoromethyl)sulfonyl)-3-oxo-3H-phenoxazin-7-yl isobutyrate
  参考文献：
  名称：

  试卤灵衍生物的区域选择性二氟甲烷磺酰化和三氟甲磺酸化

  摘要：

  本文报道了试卤灵衍生物的区域选择性二氟甲磺酰化或三氟甲磺酸化，其允许以良好收率轻松获得 2-二氟甲磺酰化或三氟甲磺酸化试卤灵衍生物。二氟甲磺酰基的安装显着增加了发色团的​​溶解度并扩大了其斯托克斯位移。与试卤灵对应物相比，基于二氟甲烷磺酰化试卤灵的荧光探针被证明能够以更强的荧光信号对活细胞中的酶活性进行成像。

  DOI：

  10.1021/acs.orglett.1c03192
• 作为产物：
  描述：

  试卤灵 、 异丁酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57%的产率得到3-oxo-3H-phenoxazin-7-yl isobutyrate
  参考文献：
  名称：

  试卤灵衍生物的区域选择性二氟甲烷磺酰化和三氟甲磺酸化

  摘要：

  本文报道了试卤灵衍生物的区域选择性二氟甲磺酰化或三氟甲磺酸化，其允许以良好收率轻松获得 2-二氟甲磺酰化或三氟甲磺酸化试卤灵衍生物。二氟甲磺酰基的安装显着增加了发色团的​​溶解度并扩大了其斯托克斯位移。与试卤灵对应物相比，基于二氟甲烷磺酰化试卤灵的荧光探针被证明能够以更强的荧光信号对活细胞中的酶活性进行成像。

  DOI：

  10.1021/acs.orglett.1c03192

文献信息

• Assessment of Acyl Groups and Reaction Conditions in the Competition between Perhydrolysis and Hydrolysis of Acyl Resorufins for Developing an Indicator Reaction for Fluorometric Analysis of Hydrogen Peroxide.
  作者：Hatsuo Maeda、Shinya Matsu-ura、Mari Nishida、Yuji Yamauchi、Hidenobu Ohmori

  DOI：10.1248/cpb.50.169

  日期：——

  Perhydrolysis of acetyl resorufin (AR) was reported previously to work as a fluorometric indicator reaction for glucose determination using only glucose oxidase. However, hydrolysis of AR in blank solution rendered the working concentration range of this method less than two orders of magnitude. To exclude or at least significantly reduce this interference, acyl groups and reaction conditions in the competition between perhydrolysis and hydrolysis of various acyl resorufins were assessed. Fluorometric evaluation of reactions in the presence or absence of H2O2 in phosphate buffer (pH 7.5, 100 mM)–CH3CN at 25 °C demonstrated that in tert-butylacetyl, isobutyryl, cyclohexanecarbonyl and pivaloyl resorufins (TBAR, IBR, CHR and PVR, respectively) among 10 acyl resorufins examined here, the competitive situation was shifted in a much more favorable way to perhydrolysis than in AR, although fluorometric responses due to their H2O2-dependent deacylation were suppressed in comparison with AR. Examination of the effects of pH, components and concentrations of buffers as well as reaction temperature established reaction conditions that not only allowed perhydrolysis of each of these four compounds to prevail over hydrolysis more effectively, but also improved the H2O2-based fluorometric responses. Thus, perhydrolysis of TBAR, IBR, CHR and PVR in phosphate buffer (pH 8.0, 20 mM)–CH3CN at 25 °C worked effectively as fluorometric indicator reactions for H2O2 analysis, affording a calibration curve over a concentration range of three orders of magnitude. Taking sensitivity, reproducibility and the response for blank solution into consideration, PVR seemed to be the best choice as a fluorochromogen for H2O2 determination under these conditions. For H2O2 analysis at lower pH, perhydrolysis of IBR in phosphate buffer (pH 7.5, 20 mM)–CH3CN was shown to effectively function as an indicator reaction. Applicability of the fluorometric methods with PVR and IBR to blood glucose determination was also discussed, comparing with Trinder's method with phenol, 4-aminoantipyrine and peroxidase (POD).

  先前报道乙酰试卤灵 (AR) 的过水解可作为仅使用葡萄糖氧化酶测定葡萄糖的荧光指示剂反应。然而，空白溶液中 AR 的水解使得该方法的工作浓度范围小于两个数量级。为了排除或至少显着减少这种干扰，评估了各种酰基试卤灵的过水解和水解之间的竞争中的酰基和反应条件。在 25 °C 下，在磷酸盐缓冲液（pH 7.5，100 mM）–CH3CN 中存在或不存在 H2O2 的情况下对反应进行荧光评估，结果表明在叔丁基乙酰基、异丁酰基、环己烷羰基和新戊酰基试卤灵 (TBAR ，IBR，CHR 和 PVR，分别）在这里检查的 10 种酰基试卤灵中，竞争形势以比 AR 更有利的方式转向过水解，尽管与 AR 相比，由于其 H2O2 依赖性脱酰化导致的荧光响应受到抑制。检查 pH 值、缓冲液成分和浓度以及反应温度的影响，建立了反应条件，不仅使这四种化合物中的每一种化合物的过水解更有效地压倒水解，而且还改善了基于 H2O2 的荧光响应。因此，TBAR、IBR、CHR 和 PVR 在磷酸盐缓冲液（pH 8.0，20 mM）–CH3CN 在 25 °C 下的过水解可有效地作为 H2O2 分析的荧光指示剂反应，提供超过三个数量级的浓度范围。考虑到灵敏度、重现性和空白溶液的响应，PVR 似乎是在这些条件下测定 H2O2 的荧光显色剂的最佳选择。对于较低 pH 下的 H2O2 分析，IBR 在磷酸盐缓冲液（pH 7.5，20 mM）–CH3CN 中的过水解被证明可以有效地发挥指示反应的作用。还讨论了 PVR 和 IBR 荧光法测定血糖的适用性，并与苯酚、4-氨基安替比林和过氧化物酶 (POD) 的 Trinder 法进行了比较。
• Regioselective Difluoromethane sulfonylation and Triflylation of Resorufin Derivatives
  作者：Qingwei Tan、Shuxuan Zhao、Yuyao Li、Jialing Jiang、Huiling Tang、Yefeng Chen、Yan Peng、Hexin Xie

  DOI：10.1021/acs.orglett.1c03192

  日期：2021.11.5

  Reported herein is a regioselective difluoromethane sulfonylation or triflylation of resorufin derivatives, which allows easy access to 2-difluoromethane sulfonylated or triflylated resorufin derivatives in good yields. The installation of a difluoromethane sulfonyl group significantly increases the solubility of the chromophore and expands its Stokes shift. A difluoromethane sulfonylated resorufin-based

  本文报道了试卤灵衍生物的区域选择性二氟甲磺酰化或三氟甲磺酸化，其允许以良好收率轻松获得 2-二氟甲磺酰化或三氟甲磺酸化试卤灵衍生物。二氟甲磺酰基的安装显着增加了发色团的​​溶解度并扩大了其斯托克斯位移。与试卤灵对应物相比，基于二氟甲烷磺酰化试卤灵的荧光探针被证明能够以更强的荧光信号对活细胞中的酶活性进行成像。