2-((2-methyl-9,10-dihydro-8H-pyrano[2,3-h]quinolin-8-yl)thio)ethanol | 1427512-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 2-((2-methyl-9,10-dihydro-8H-pyrano[2,3-h]quinolin-8-yl)thio)ethanol
• 英文别名: 2-[(2-methyl-9,10-dihydro-8H-pyrano[2,3-h]quinolin-8-yl)sulfanyl]ethanol
• CAS: 1427512-50-2
• 化学式: C₁₅H₁₇NO₂S
• 分子量: 275.371
• InChiKey: QYUPNLOAIWUKID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-(hydroxymethyl)-2-methylquinolin-7-ol 以 水 、 乙腈 为溶剂， 反应 10.0h， 生成 2-((2-methyl-9,10-dihydro-8H-pyrano[2,3-h]quinolin-8-yl)thio)ethanol
  参考文献：
  名称：

  A Bioorthogonal Ligation Enabled by Click Cycloaddition ofo-Quinolinone Quinone Methide and Vinyl Thioether

  摘要：

  There is an increasing interest in the use of bioorthogonal ligation to advance biomedical research through selective labeling of biomolecules in living systems. Accordingly, discovering new reactions to expand the toolbox of bioorthogonal chemistry is of particular interest to chemical biologists. Herein we report a new bioorthogonal ligation enabled by click hetero-Diels-Alder (HDA) cycloaddition of in situ-generated o-quinolinone quinone methides and vinyl thioethers. This reaction is highly selective and proceeds smoothly under aqueous conditions. The functionalized vinyl thioethers are small and chemically stable in vivo, making them suitable for use as bioorthogonal chemical reporters that can be effectively coupled to various biomolecules. We utilized this bioorthogonal ligation for site-specific labeling of proteins as well as imaging of bioactive small molecules inside live cells.

  DOI：

  10.1021/ja401989p

文献信息

• Computation-Guided Development of the “Click” <i>ortho</i>-Quinone Methide Cycloaddition with Improved Kinetics
  作者：Xiaoyun Zhang、Shuo-Qing Zhang、Qiang Li、Fan Xiao、Zongwei Yue、Xin Hong、Xiaoguang Lei

  DOI：10.1021/acs.orglett.0c00578

  日期：2020.4.17

  rate-determining step of this transformation, and two highly reactive oQQM precursors were predicted. Guided by the calculations, a new “click” oQM cycloaddition which shows significantly improved kinetics and remarkable efficiency on protein labeling was developed.

  我们在这里报告的“点击”的深层机理研究邻-quinone甲基化物（Ø QM）环之间的邻-喹啉醌甲基化物（Ò QQM）和硫基-乙烯基醚（TV），命名为TQ-结扎。DFT计算揭示了意想不到的事实，即脱水ö QQM前体是这样的转变的速率决定步骤，以及两个高反应性ö QQM前体进行了预测。通过计算的指导下，一个新的“点击” Ø QM环，显示显著改善动力学和蛋白标记效率惊人的开发。