N-(2-chloromethylquinolin-6-yl)carbamic acid benzyl ester | 784157-42-2

• 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: N-(2-chloromethylquinolin-6-yl)carbamic acid benzyl ester
• CAS: 784157-42-2
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: ILEFVDVPBNMMEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(2-chloromethylquinolin-6-yl)carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 6-amino-2-N,N-bis(2-pyridylmethyl)aminomethylquinoline
  参考文献：
  名称：

  Development of a Zinc Ion-Selective Luminescent Lanthanide Chemosensor for Biological Applications

  摘要：

  Detection of chelatable zinc (Zn2+) in biological studies has attracted much attention recently, because chelatable Zn2+ plays important roles in many biological systems. Lanthanicle complexes (Eu3+, Tb3+, etc.) have excellent spectroscopic properties for biological applications, such as long luminescence lifetimes of the order of milliseconds, a large Stoke's shift of >200 nm, and high water solubility. Herein, we present the design and synthesis of a novel lanthanide sensor molecule, [Eu-7], for detecting Zn2+. This europium (Eu3+) complex employs a quinolyl ligand as both a chromophore and an acceptor for Zn2+. Upon addition of Zn2+ to a solution of [Eu-7], the luminescence of Eu3+ is strongly enhanced, with high selectivity for Zn2+ over other biologically relevant metal cations. One of the important advantages of [Eu-7] is that this complex can be excited with longer excitation wavelengths (around 340 nm) as compared with previously reported Zn2+-sensitive luminescent lamthanide sensors, whose excitation wavelength is at too high an energy level for biological applications. The usefulness of [Eu-7] for monitoring Zn2+ changes in living HeLa cells was confirmed. This novel Zn2+-selective luminescent lanthanide chemosensor [Eu-7] should be an excellent lead compound for the development of a range of novel luminescent lanthanide chemosensors for biological applications.

  DOI：

  10.1021/ja0469333
• 作为产物：
  描述：

  N-(2-methylquinolin-6-yl)carbamic acid benzyl ester 在 对甲苯磺酰氯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 N-(2-chloromethylquinolin-6-yl)carbamic acid benzyl ester
  参考文献：
  名称：

  Development of a Zinc Ion-Selective Luminescent Lanthanide Chemosensor for Biological Applications

  摘要：

  Detection of chelatable zinc (Zn2+) in biological studies has attracted much attention recently, because chelatable Zn2+ plays important roles in many biological systems. Lanthanicle complexes (Eu3+, Tb3+, etc.) have excellent spectroscopic properties for biological applications, such as long luminescence lifetimes of the order of milliseconds, a large Stoke's shift of >200 nm, and high water solubility. Herein, we present the design and synthesis of a novel lanthanide sensor molecule, [Eu-7], for detecting Zn2+. This europium (Eu3+) complex employs a quinolyl ligand as both a chromophore and an acceptor for Zn2+. Upon addition of Zn2+ to a solution of [Eu-7], the luminescence of Eu3+ is strongly enhanced, with high selectivity for Zn2+ over other biologically relevant metal cations. One of the important advantages of [Eu-7] is that this complex can be excited with longer excitation wavelengths (around 340 nm) as compared with previously reported Zn2+-sensitive luminescent lamthanide sensors, whose excitation wavelength is at too high an energy level for biological applications. The usefulness of [Eu-7] for monitoring Zn2+ changes in living HeLa cells was confirmed. This novel Zn2+-selective luminescent lanthanide chemosensor [Eu-7] should be an excellent lead compound for the development of a range of novel luminescent lanthanide chemosensors for biological applications.

  DOI：

  10.1021/ja0469333

文献信息

• Time-Resolved Long-Lived Luminescence Imaging Method Employing Luminescent Lanthanide Probes with a New Microscopy System
  作者：Kenjiro Hanaoka、Kazuya Kikuchi、Shigeru Kobayashi、Tetsuo Nagano

  DOI：10.1021/ja073392j

  日期：2007.11.1

  luminescence to be selectively imaged. Usual time-resolved fluorescence microscopy provides fluorescence images with nanosecond resolution and has been used to image interactions between proteins, protein phosphorylation, the local pH, the refractive index, ion or oxygen concentrations, etc. Luminescent lanthanide complexes (especially europium and terbium trivalent ions (Eu3+ and Tb3+)), in contrast

  对生物现象的详细研究需要卓越的荧光成像方法，一种允许精确分析的方法是时间分辨荧光测量，它提供高信噪比。在此，我们描述了一种新的荧光成像系统，通过时间分辨、长寿命发光显微镜 (TRLLM) 来可视化活生物样品中的生物分子。在 TRLLM 中，短寿命的背景荧光和散射光被门控，从而可以选择性地对长寿命的发光进行成像。通常的时间分辨荧光显微镜提供具有纳秒分辨率的荧光图像，并已用于对蛋白质、蛋白质磷酸化、局部 pH 值、折射率、离子或氧浓度等之间的相互作用进行成像。相比之下，发光镧系元素配合物（尤其是铕和铽三价离子（Eu3+ 和 Tb3+））具有毫秒级的长发光寿命。我们设计并合成了用于 TRLLM 的新型发光 Eu3+ 配合物，并开发了一种新的 TRLLM 系统，该系统使用传统的荧光显微镜，带有用于门控信号采集的图像增强器单元和氙气闪光灯作为激发源。当新开发的发光Eu3+配合物应用于活细胞时，TRL