N-pyridin-3-yl-3-[2-[[3-(pyridin-3-ylcarbamoyl)naphthalen-2-yl]oxymethyl]prop-2-enoxy]naphthalene-2-carboxamide | 1269185-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-pyridin-3-yl-3-[2-[[3-(pyridin-3-ylcarbamoyl)naphthalen-2-yl]oxymethyl]prop-2-enoxy]naphthalene-2-carboxamide
• CAS: 1269185-14-9
• 化学式: C₃₆H₂₈N₄O₄
• 分子量: 580.643
• InChiKey: LLKGXWZNEWQSQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-pyridin-3-yl-3-[2-[[3-(pyridin-3-ylcarbamoyl)naphthalen-2-yl]oxymethyl]prop-2-enoxy]naphthalene-2-carboxamide 反应 0.83h， 以80%的产率得到3-hydroxy-4-[2-[[2-hydroxy-3-(pyridin-3-ylcarbamoyl)naphthalen-1-yl]methyl]prop-2-enyl]-N-pyridin-3-ylnaphthalene-2-carboxamide
  参考文献：
  名称：

  Two new fluorescent Zn²⁺ sensors exhibiting different sensing mode with subtle structural changes

  摘要：

  Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised. Both receptors showed highly selective coordination towards Zn2+ and exhibited diverse sensing behaviour due to the structural variations. HL-1 showed monotonous turn-on' response towards Zn2+ while HL-2 displayed highly Zn2+ sensitive turn on' and ratiometric' properties. Detailed Job plot experiment, single crystal data, H-1 NMR, ESI-MS, UV-vis and density functional theory calculation studies were conducted to understand the binding modes of HL-1 and HL-2 with Zn2+. These results revealed the binding stoichiometric ratio between receptors and Zn2+ were 1:1 with low detection limits and high binding constants.[GRAPHICS].Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised via TCR reaction. Both of them showed selective coordination to Zn2+ ions but exhibited incongruent sensing mode due to structural variations. HL-1 showed monotonous 'turn-on' whereas HL-2 displayed highly sensitive 'turn on' and 'ratiometric' properties towards Zn2+.

  DOI：

  10.1080/10610278.2016.1242730
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 氯化亚砜 、 硫酸 、 potassium tert-butylate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 N-pyridin-3-yl-3-[2-[[3-(pyridin-3-ylcarbamoyl)naphthalen-2-yl]oxymethyl]prop-2-enoxy]naphthalene-2-carboxamide
  参考文献：
  名称：

  Two new fluorescent Zn²⁺ sensors exhibiting different sensing mode with subtle structural changes

  摘要：

  Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised. Both receptors showed highly selective coordination towards Zn2+ and exhibited diverse sensing behaviour due to the structural variations. HL-1 showed monotonous turn-on' response towards Zn2+ while HL-2 displayed highly Zn2+ sensitive turn on' and ratiometric' properties. Detailed Job plot experiment, single crystal data, H-1 NMR, ESI-MS, UV-vis and density functional theory calculation studies were conducted to understand the binding modes of HL-1 and HL-2 with Zn2+. These results revealed the binding stoichiometric ratio between receptors and Zn2+ were 1:1 with low detection limits and high binding constants.[GRAPHICS].Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised via TCR reaction. Both of them showed selective coordination to Zn2+ ions but exhibited incongruent sensing mode due to structural variations. HL-1 showed monotonous 'turn-on' whereas HL-2 displayed highly sensitive 'turn on' and 'ratiometric' properties towards Zn2+.

  DOI：

  10.1080/10610278.2016.1242730

文献信息

• Two-mode selective sensing of <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si1.gif" overflow="scroll"><mml:mrow><mml:msub><mml:mrow><mml:mtext>H</mml:mtext></mml:mrow><mml:mrow><mml:mn>2</mml:mn></mml:mrow></mml:msub><mml:mmultiscripts><mml:mrow><mml:mtext>PO</mml:mtext></mml:mrow><mml:mrow><mml:mn>4</mml:mn></mml:mrow><mml:none /><mml:none /><mml:mrow><mml:mo>-</mml:mo></mml:mrow></mml:mmultiscripts></mml:mrow></mml:math> controlled by intramolecular hydrogen bonding as the valve
  作者：Wei-tao Gong、Shuang Bao、Fu-rui Wang、Jun-wei Ye、Gui-ling Ning、Kazuhisa Hiratani

  DOI：10.1016/j.tetlet.2010.11.147

  日期：2011.2

  A novel fluorescent sensor L1 exhibiting selective H2PO4- sensing ability was synthesized. The initial conformation of L1 was controlled via intramolecular hydrogen bonding and the switching/gating function was achieved by disturbing the intramolecular hydrogen bonds before and after interaction with H2PO4-.

  新型荧光传感器L1具有选择性H2个采购订单4--合成感测能力。L1的初始构象是通过分子内氢键控制的，而开关/门控功能是通过干扰与之相互作用之前和之后的分子内氢键来实现的。H2个采购订单4--。
• Two new fluorescent Zn²⁺ sensors exhibiting different sensing mode with subtle structural changes
  作者：Hassan Mehdi、Hongchang Pang、Weitao Gong、Ali Wajahat、Kalavathi Dhinakaran Manivannan、Shaheen Shah、Jun-wei Ye、Guiling Ning

  DOI：10.1080/10610278.2016.1242730

  日期：2017.5.4

  Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised. Both receptors showed highly selective coordination towards Zn2+ and exhibited diverse sensing behaviour due to the structural variations. HL-1 showed monotonous turn-on' response towards Zn2+ while HL-2 displayed highly Zn2+ sensitive turn on' and ratiometric' properties. Detailed Job plot experiment, single crystal data, H-1 NMR, ESI-MS, UV-vis and density functional theory calculation studies were conducted to understand the binding modes of HL-1 and HL-2 with Zn2+. These results revealed the binding stoichiometric ratio between receptors and Zn2+ were 1:1 with low detection limits and high binding constants.[GRAPHICS].Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised via TCR reaction. Both of them showed selective coordination to Zn2+ ions but exhibited incongruent sensing mode due to structural variations. HL-1 showed monotonous 'turn-on' whereas HL-2 displayed highly sensitive 'turn on' and 'ratiometric' properties towards Zn2+.