7-bromo-6-((5-bromo-1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)(o-tolyl)methyl)-1-methyl-1,2,3,4-tetrahydroquinoline | 1253592-08-3

• 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: 7-bromo-6-((5-bromo-1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)(o-tolyl)methyl)-1-methyl-1,2,3,4-tetrahydroquinoline
• 英文别名: bis(7-bromo-1,2,3,4-tetrahydro-1-methylquinolin-6-yl)(2-tolyl)methane；7-bromo-6-[(7-bromo-1-methyl-3,4-dihydro-2H-quinolin-6-yl)-(2-methylphenyl)methyl]-1-methyl-3,4-dihydro-2H-quinoline
• CAS: 1253592-08-3
• 化学式: C₂₈H₃₀Br₂N₂
• 分子量: 554.368
• InChiKey: HDOKVFTXYDYFHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-bromo-6-((5-bromo-1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)(o-tolyl)methyl)-1-methyl-1,2,3,4-tetrahydroquinoline 、 二氯二甲基硅烷 在 仲丁基锂 、 四氯苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 以16%的产率得到
  参考文献：
  名称：

  Development of NIR Fluorescent Dyes Based on Si–rhodamine for in Vivo Imaging

  摘要：

  We have developed a series of novel near-infrared (NIR) wavelength-excitable fluorescent dyes, SiR-NIRs, by modifying the Si-rhodamine scaffold to obtain emission in the range suitable for in vivo imaging. Among them, SiR680 and SiR700 showed sufficiently high quantum efficiency in aqueous media. Both antibody-bound and free dye exhibited high tolerance to photobleaching in aqueous solution. Subcutaneous xenograft tumors were successfully visualized in a mouse tumor model using SiR700-labeled anti-tenascin-C (TN-C) antibody, SiR700-RCB1. SiR-NIRs are expected to be useful as labeling agents for in vivo imaging studies including multicolor imaging, and also as scaffolds for NW fluorescence probes.

  DOI：

  10.1021/ja210375e
• 作为产物：
  描述：

  7-溴喹啉 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.17h， 生成 7-bromo-6-((5-bromo-1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)(o-tolyl)methyl)-1-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  [EN] SILYL BRIDGED DYES
  [FR] COLORANTS À PONT SILYLE

  摘要：

  Provided herein are fluorescent dyes possessing a broad range of silyl modifications, which can be used, for example, for enabling brighter dyes, red-shifting of fluorescence, and as handles,e.g., for the introduction of sensors and/or targeting groups, including no-wash fluorogenic labeling agents for nuclear DNA, SnapTag® proteins, and HaloTag® proteins. The fluorescent dyes have the following structure: or a tautomer thereof, or a salt of the foregoing, wherein values for the variables (e.g., X, Z1, Z2, R3, R6, R7, R11) are as described herein.

  公开号：

  WO2023064790A1

文献信息

• Silicon functionalization expands the repertoire of Si-rhodamine fluorescent probes
  作者：Desaboini Nageswara Rao、Xincai Ji、Stephen C. Miller

  DOI：10.1039/d2sc01821g

  日期：——

  molecules. Si-rhodamines, in which the bridging oxygen of rhodamines is replaced with a dimethyl silyl group, are increasingly the dye scaffold of choice for biological applications, as fluorescence is shifted into the near-infrared while maintaining high brightness. Despite intense interest in Si-rhodamines, there has been no exploration of the scope of silicon functionalization in these dyes, a potential

  荧光染料如罗丹明被广泛用于测定活性和成像其他不可见分子的位置。Si-罗丹明，其中罗丹明的桥氧被二甲基甲硅烷基取代，越来越成为生物应用的首选染料支架，因为荧光转移到近红外，同时保持高亮度。尽管对 Si-罗丹明有浓厚的兴趣，但尚未探索这些染料中硅功能化的范围，这是传统罗丹明中不存在的潜在修饰位点。在这里，我们报告了广泛的甲硅烷基修饰，这些修饰可以使染料更亮，进一步红移，调节荧光的新方法，以及引入染料附着手柄，包括用于核 DNA 的荧光标记剂，SNAP 标记和 HaloTag 标记。因此，对桥接硅的修改对于改进和扩展所有 Si 染料的应用具有广泛的用途。