ethyl 2-[(4,5-dicyanonaphthalen-1-yl)amino]acetate | 1447722-56-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-[(4,5-dicyanonaphthalen-1-yl)amino]acetate
• 英文别名: Ethyl 2-[(4,5-dicyanonaphthalen-1-yl)amino]acetate
• CAS: 1447722-56-6
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: OUSOYGORCIDMNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  85.9
• 氢给体数：
  1
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-azidonaphthalene-1,8-dicarbonitrile	465498-42-4	C12H5N5	219.205

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-[(4,5-dicyanonaphthalen-1-yl)amino]acetic Acid	1447722-52-2	C14H9N3O2	251.244

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(4,5-dicyanonaphthalen-1-yl)amino]acetate 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以95%的产率得到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 tetrahydroborate 、 sodium azide 、 吡啶硼烷 、 sodium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 20.5h， 生成 ethyl 2-[(4,5-dicyanonaphthalen-1-yl)amino]acetate
  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

文献信息

• 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.