Ethyl 7-nitropyrene-2-carboxylate | 180623-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: Ethyl 7-nitropyrene-2-carboxylate
• CAS: 180623-85-2
• 化学式: C₁₉H₁₃NO₄
• 分子量: 319.317
• InChiKey: HKKGRWRBPVYQKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 7-nitropyrene-2-carboxylate 在 tin(ll) chloride 作用下， 以 乙酸乙酯 为溶剂， 以74%的产率得到Ethyl 7-aminopyrene-2-carboxylate
  参考文献：
  名称：

  7-Amino-2-pyrenecarboxylic Acid

  摘要：

  Pyrenes undergo initial electrophilic substitution in the 1 position; a second substitution typically occurs in the 3, 6, or 8 positions. We sought a pyrene with synthetically useful handles in the unusual 2,7 substitution pattern. To that end, 7-amino-2-pyrenecarboxylic acid was prepared by partial reduction of pyrene to 4,5,9,10-tetrahydropyrene, Friedel-Crafts acylation in the 2 position, and conversion to 2-carbethoxytetrahydropyrene through the haloform reaction and esterification. Nitration of the ester proceeded in the 7 position; rearomatization, reduction of the nitro group, and saponification gave the title compound.

  DOI：

  10.1021/jo951966+
• 作为产物：
  描述：

  Ethyl 7-nitro-4,5,9,10-tetrahydropyrene-2-carboxylate 在 溴 作用下， 以 二硫化碳 为溶剂， 以92%的产率得到Ethyl 7-nitropyrene-2-carboxylate
  参考文献：
  名称：

  7-Amino-2-pyrenecarboxylic Acid

  摘要：

  Pyrenes undergo initial electrophilic substitution in the 1 position; a second substitution typically occurs in the 3, 6, or 8 positions. We sought a pyrene with synthetically useful handles in the unusual 2,7 substitution pattern. To that end, 7-amino-2-pyrenecarboxylic acid was prepared by partial reduction of pyrene to 4,5,9,10-tetrahydropyrene, Friedel-Crafts acylation in the 2 position, and conversion to 2-carbethoxytetrahydropyrene through the haloform reaction and esterification. Nitration of the ester proceeded in the 7 position; rearomatization, reduction of the nitro group, and saponification gave the title compound.

  DOI：

  10.1021/jo951966+

文献信息

• 7-Amino-2-pyrenecarboxylic Acid
  作者：Abdallah Musa、Bhama Sridharan、Hyoyoung Lee、Daniell Lewis Mattern

  DOI：10.1021/jo951966+

  日期：1996.1.1

  Pyrenes undergo initial electrophilic substitution in the 1 position; a second substitution typically occurs in the 3, 6, or 8 positions. We sought a pyrene with synthetically useful handles in the unusual 2,7 substitution pattern. To that end, 7-amino-2-pyrenecarboxylic acid was prepared by partial reduction of pyrene to 4,5,9,10-tetrahydropyrene, Friedel-Crafts acylation in the 2 position, and conversion to 2-carbethoxytetrahydropyrene through the haloform reaction and esterification. Nitration of the ester proceeded in the 7 position; rearomatization, reduction of the nitro group, and saponification gave the title compound.