4-azidonaphthalene-1,8-dicarbonitrile | 465498-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-azidonaphthalene-1,8-dicarbonitrile
• 英文别名: 4-Azidonaphthalene-1,8-dicarbonitrile
• CAS: 465498-42-4
• 化学式: C₁₂H₅N₅
• 分子量: 219.205
• InChiKey: DYBGQXMUDKIUIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-azidonaphthalene-1,8-dicarbonitrile 在 sodium tetrahydroborate 、 吡啶硼烷 、 sodium sulfate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 38.0h， 生成 2-[(4,5-dicyanonaphthalen-1-yl)amino]acetic Acid
  参考文献：
  名称：

  Synthesis of a Hydrophilic Naphthalimidedioxime

  摘要：

  Imidedioximes are formed in hydroxylamine-treated polyacrylonitrile adsorbents used in the extraction of uranium from seawater. Although known to be a good uranophile, the glutarimidedioxime model compound 1 is rapidly hydrolyzed under acidic conditions used to elute metals from the adsorbent. This work reports the synthesis of a hydrophilic naphthalimidedioxime derivative 14, which is stable under acidic elution conditions. The synthesis starts from simple acenaphthenequinone 7 and converts it to a functional group dense imidedioxime 14 in 7 steps.

  DOI：

  10.1021/jo4009386
• 作为产物：
  描述：

  4-bromonaphthalene-1,8-dicarbonitrile 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 以94%的产率得到4-azidonaphthalene-1,8-dicarbonitrile
  参考文献：
  名称：

  4-Amino-1,8-dicyanonaphthalene derivatives as novel fluorophore and fluorescence switches: efficient synthesis and fluorescence enhancement induced by transition metal ions and protons

  摘要：

  A new electronic push-pull fluorophore. 4-amino-1,8-dicyanonaphthalene, and its derivatives have been synthesized efficiently. They can be used as photo-induced electron transfer fluorescence switches which exhibit considerable fluorescence enhancement induced by transition metal ions Cr3+ and Fe3+ and also respond to pH values very sensitively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00441-0

文献信息

• 4-Amino-1,8-dicyanonaphthalene derivatives as novel fluorophore and fluorescence switches: efficient synthesis and fluorescence enhancement induced by transition metal ions and protons
  作者：Xuhong Qian、Yi Xiao

  DOI：10.1016/s0040-4039(02)00441-0

  日期：2002.4

  A new electronic push-pull fluorophore. 4-amino-1,8-dicyanonaphthalene, and its derivatives have been synthesized efficiently. They can be used as photo-induced electron transfer fluorescence switches which exhibit considerable fluorescence enhancement induced by transition metal ions Cr3+ and Fe3+ and also respond to pH values very sensitively. (C) 2002 Published by Elsevier Science Ltd.
• Synthesis of a Hydrophilic Naphthalimidedioxime
  作者：Christopher D. Grant、Sung Ok Kang、Benjamin P. Hay

  DOI：10.1021/jo4009386

  日期：2013.8.2

  Imidedioximes are formed in hydroxylamine-treated polyacrylonitrile adsorbents used in the extraction of uranium from seawater. Although known to be a good uranophile, the glutarimidedioxime model compound 1 is rapidly hydrolyzed under acidic conditions used to elute metals from the adsorbent. This work reports the synthesis of a hydrophilic naphthalimidedioxime derivative 14, which is stable under acidic elution conditions. The synthesis starts from simple acenaphthenequinone 7 and converts it to a functional group dense imidedioxime 14 in 7 steps.