N-(1-pyrenylmethyl)propargylamine | 690661-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-(1-pyrenylmethyl)propargylamine
• 英文别名: N-(pyren-1-ylmethyl)prop-2-yn-1-amine
• CAS: 690661-34-8
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: WHPVIXBSJHVUTC-UHFFFAOYSA-N

物化性质

• 沸点：
  477.8±20.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-pyrenylmethyl)propargylamine 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 三氯乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 5-[3-(1-pyrenylmethylamino)propynyl]-2'-deoxyuridine
  参考文献：
  名称：

  Pyrene-Labeled Base-Discriminating Fluorescent DNA Probes for Homogeneous SNP Typing

  摘要：

  This paper describes the design of novel base-discriminating fluorescent (BDF) nucleobases and their application to single nucleotide polymorphism (SNP) typing. We devised novel BDF nucleosides, U-Py and C-Py, which contain a pyrenecarboxamide chromophore connected by a propargyl linker. The fluorescence spectrum of the duplex containing a U-Py/A base pair showed a strong emission at 397 nm on 327 nm excitation. In contrast, the fluorescence of duplexes containing U-Py/N base pairs (N = C, G, or T) was considerably weaker. The proposed structure of the duplex containing a matched U-Py/A base pair suggests that the high polarity near the pyrenecarboxamide group is responsible for the strong A-selective fluorescence emission. Moreover, the fluorescence of the duplex containing a U-Py/A base pair was not quenched by a flanking C/G base pair. The fluorescence properties are quite different from previous BDF nucleobases, where fluorescence is quenchable by flanking C/G base pairs. The duplex containing the C derivative, C-Py, selectively emitted fluorescence when the base opposite C-Py was G. The drastic change of fluorescence intensity by the nature of the complementary base is extremely useful for SNP typing. U-Py- and C-Py-containing oligodeoxynucleotides acted as effective reporter probes for homogeneous SNP typing of DNA samples containing c-Ha-ras and BRCA2 SNP sites.

  DOI：

  10.1021/ja039625y
• 作为产物：
  描述：

  1-芘甲醛 、 炔丙胺 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以77%的产率得到N-(1-pyrenylmethyl)propargylamine
  参考文献：
  名称：

  Pyrene-Labeled Base-Discriminating Fluorescent DNA Probes for Homogeneous SNP Typing

  摘要：

  This paper describes the design of novel base-discriminating fluorescent (BDF) nucleobases and their application to single nucleotide polymorphism (SNP) typing. We devised novel BDF nucleosides, U-Py and C-Py, which contain a pyrenecarboxamide chromophore connected by a propargyl linker. The fluorescence spectrum of the duplex containing a U-Py/A base pair showed a strong emission at 397 nm on 327 nm excitation. In contrast, the fluorescence of duplexes containing U-Py/N base pairs (N = C, G, or T) was considerably weaker. The proposed structure of the duplex containing a matched U-Py/A base pair suggests that the high polarity near the pyrenecarboxamide group is responsible for the strong A-selective fluorescence emission. Moreover, the fluorescence of the duplex containing a U-Py/A base pair was not quenched by a flanking C/G base pair. The fluorescence properties are quite different from previous BDF nucleobases, where fluorescence is quenchable by flanking C/G base pairs. The duplex containing the C derivative, C-Py, selectively emitted fluorescence when the base opposite C-Py was G. The drastic change of fluorescence intensity by the nature of the complementary base is extremely useful for SNP typing. U-Py- and C-Py-containing oligodeoxynucleotides acted as effective reporter probes for homogeneous SNP typing of DNA samples containing c-Ha-ras and BRCA2 SNP sites.

  DOI：

  10.1021/ja039625y

文献信息

• Water compatible triazole linked pyrene-C1-glucosyl fluorescent sensor for Au3+ and living cell imaging studies
  作者：Samiul Islam Hazarika、Bholanath Dolai、Ananta Kumar Atta

  DOI：10.1016/j.molstruc.2019.127272

  日期：2020.2

  fluorescent sensor 1 for selective recognition of Au3+ in aqueous medium at physiological pH. The sensor provides important features such as high selectivity and sensitivity, low detection limit, reversibility and quick response time. The selectivity of 1 towards Au3+ ion is established by changes of absorbance and fluorescence in the presence of Au3+ ions. The formation of 1:1 complex (1-Au3+) was established

  摘要我们报道了一种简单的三唑连接芘附加碳水化合物的“关闭”荧光传感器 1，用于在生理 pH 值下选择性识别水性介质中的 Au3+。该传感器具有高选择性和灵敏度、低检测限、可逆性和快速响应时间等重要特性。1 对 Au3+ 离子的选择性是通过在 Au3+ 离子存在下吸光度和荧光的变化来确定的。1:1 复合物 (1-Au3+) 的形成是由 Job 的情节确定的，并得到了 ESI-MS 数据的支持。此外，该传感器已用于识别活细胞中的 Au3+ 离子。
• SUPRAMOLECULAR ENCRYPTED FLUORESCENT SECURITY INK COMPOSITIONS
  申请人：Northwestern University

  公开号：US20160137864A1

  公开（公告）日：2016-05-19

  Fluorescent dyes, ink compositions comprising the dyes, methods and devices for printing the ink compositions, images printed using the ink compositions and methods for authenticating the printed images are provided. The fluorescent dyes are heterorotaxanes that include large macrocyclic rings around fluorophores and are capable of emitting solid-state fluorescence. When the heterorotaxanes are combined with encapsulating agents and competitive binding agents in aqueous solution, the resulting ink composition exhibits a complex, dynamic equilibrium that provides a tunable fluorescence emission spectrum with a non-linear response to the dye concentration.
• SUPRAMOLECULAR FLUORESCENT DYES
  申请人：Northwestern University

  公开号：US20160137845A1

  公开（公告）日：2016-05-19

  Fluorescent dyes are provided. The fluorescent dyes are heterorotaxanes that include large macrocyclic rings around fluorophores and are capable of emitting solid-state fluorescence.