6-ethynyl-N,N-dimethylnaphthalen-2-amine | 1429057-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-ethynyl-N,N-dimethylnaphthalen-2-amine
• 英文别名: 6-Ethynyl-N,N-dimethylnaphthalen-2-amine
• CAS: 1429057-58-8
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: LKMJRBJOKOALRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-ethynyl-N,N-dimethylnaphthalen-2-amine 在 四甲基乙二胺 、 铜 、 戴斯-马丁氧化剂 、 copper(l) chloride 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成 7-(6-(dimethylamino)naphthalen-2-yl)hepta-2,4,6-triynal
  参考文献：
  名称：

  Near-Infrared Fluorescent Probes with Rotatable Polyacetylene Chains for the Detection of Amyloid-β Plaques

  摘要：

  DOI：

  10.1021/acs.jpcb.0c08845
• 作为产物：
  描述：

  6-bromo-N-methyl-2-naphthylamine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 potassium carbonate 、 二环己胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 6-ethynyl-N,N-dimethylnaphthalen-2-amine
  参考文献：
  名称：

  一种荧光激酶抑制剂，在结合时表现出诊断性的变化。

  摘要：

  描述了在结合激酶后显示出有利的溶剂变色性质的荧光LCK抑制剂的开发。荧光特性是通过在ATP竞争性激酶抑制剂的药效基团中包含前生荧光团来实现的。荧光滴定实验证明了该抑制剂的溶剂变色性质，其中在结合LCK时清楚地观察到发射强度的显着增加和发射最大值的变色移动。细胞环境中的显微镜实验以及流式细胞仪表明，抑制剂的荧光强度与LCK浓度相关。此外，

  DOI：

  10.1002/anie.201909536

文献信息

• Desulfitative Sonogashira cross-coupling of thiopyronin for the synthesis of NIR arylacetylene-containing rhodamines
  作者：Guangshuai Zhou、Nathaniel Finney、Yali Wang

  DOI：10.1039/d3cc05995b

  日期：2024.3.12

  A classical, safe and efficient red-shift strategy contributing to NIR arylacetylene-containing rhodamines has been developed via the desulfitative Sonogashira cross-coupling reaction of thiopyronin for the first time, exhibiting a broad substrate scope with good yields. In addition, compound 3m shows great potential for application as a singlet oxygen probe, demonstrating the practicality of the method

  首次通过硫代吡罗宁的脱硫 Sonogashira 交叉偶联反应开发了一种经典、安全且高效的红移策略，有助于产生近红外芳基乙炔含罗丹明，该策略具有广泛的底物范围和良好的产率。此外，化合物3m显示出作为单线态氧探针的巨大应用潜力，证明了该方法的实用性。
• JP5946170
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of solvatofluorochromic 7-arylethynylated 7-deaza-2′-deoxyadenosine derivatives: application to the design of environmentally sensitive fluorescent probes forming stable DNA duplexes
  作者：Azusa Suzuki、Kohki Kimura、Shinya Ishioroshi、Isao Saito、Nobukatsu Nemoto、Yoshio Saito

  DOI：10.1016/j.tetlet.2013.02.063

  日期：2013.5

  We synthesized environmentally sensitive fluorescent (ESF) 7-deaza-2'-deoxyadenosine derivatives including ethynylanthracene substituted (atz)A (1) and ethynylnaphthalene substituted (nz)A (2a), (cnz)A (2b), (anz)A (2c), and (dnz)A (2d), and investigated their photophysical properties. Among them, only push-pull type cyano- and acetyl-substituted naphthylethynylated 7-deaza-2'-deoxyadenosine, (cnz)A (2b) and (anz)A (2c), exhibited remarkable solvatofluorochromic properties (Delta lambda = 71 and 63 nm, respectively). We incorporated non-solvatofluorochromic (atz)A (1) and solvatofluorochromic (cnz)A (2b) into oligodeoxynucleotides and found that (cnz)A (2b) forms a stable base pair with both thymine and cytosine, being accompanied by a change of fluorescence intensity. Such ESF nucleosides can be used for studying structures and functions of nucleic acids. (C) 2013 Elsevier Ltd. All rights reserved.
• C2-substituted 8-aza-7-deaza-2′-deoxyadenosines as environmentally sensitive fluorescent nucleosides for discriminating apurinic/apyrimidinic sites in DNA duplex
  作者：Takumi Yamauchi、Takuya Takeda、Masaki Yanagi、Noriki Takahashi、Azusa Suzuki、Yoshio Saito

  DOI：10.1016/j.tetlet.2016.11.029

  日期：2017.1

  We synthesized various C2-naphthylethynylated 8-aza-7-deaza-2'-deoxyadenosines la-lc as novel environmentally sensitive fluorescent (ESF) purine nucleosides. In particular, the N,N-dimethylaminosubstituted derivative is exhibits a remarkably high solvatochromicity (Delta lambda = 111 nm). 1c-containing oligodeoxynucleotide (ODN) probes clearly discriminated an apurinic/apyrimidinic site (AP site) in the complementary strand via a change in emission wavelength and intensity when hybridized with a target ODN. (C) 2016 Elsevier Ltd. All rights reserved.
• Near-Infrared Fluorescent Probes with Rotatable Polyacetylene Chains for the Detection of Amyloid-β Plaques
  作者：Longfei Zhang、Xin Gong、Chuan Tian、Hualong Fu、Hongwei Tan、Jiapei Dai、Mengchao Cui

  DOI：10.1021/acs.jpcb.0c08845

  日期：2021.1.21