N-[(2Z,4Z)-8-ethynyl-4-(hydroxyimino)-3-azatricyclo[7.3.1.0⁵,¹³]-trideca-1(12),5,7,9(13),10-pentaen-2-ylidene]hydroxylamine | 1447823-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(2Z,4Z)-8-ethynyl-4-(hydroxyimino)-3-azatricyclo[7.3.1.0⁵,¹³]-trideca-1(12),5,7,9(13),10-pentaen-2-ylidene]hydroxylamine
• 英文别名: N-[6-ethynyl-3-(hydroxyamino)benzo[de]isoquinolin-1-ylidene]hydroxylamine
• CAS: 1447823-40-6
• 化学式: C₁₄H₉N₃O₂
• 分子量: 251.244
• InChiKey: SVPUUQKXYGHUNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2Z,4Z)-8-ethynyl-4-(hydroxyimino)-3-azatricyclo[7.3.1.0⁵,¹³]-trideca-1(12),5,7,9(13),10-pentaen-2-ylidene]hydroxylamine 在 copper(ll) sulfate pentahydrate 、 L-sodium ascorbate 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 2-[4-[(2Z,4Z)-2,4-bis(hydroxyimino)-3-azatricyclo[7.3.1.0⁵,¹³]-trideca-1(12),5,7,9(13),10-pentaen-8-yl]-1H-1,2,3-triazol-1-yl]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-[2-(trimethylsilyl)ethynyl]naphthalene-1,8-dicarbonitrile 在 盐酸羟胺 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以95%的产率得到N-[(2Z,4Z)-8-ethynyl-4-(hydroxyimino)-3-azatricyclo[7.3.1.0⁵,¹³]-trideca-1(12),5,7,9(13),10-pentaen-2-ylidene]hydroxylamine
  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