1,9-二氢芘 | 28862-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 1,9-二氢芘
• 英文名称: 1,9-dihydropyrene (4,6)
• 英文别名: 1,9-Dihydropyren；1,9-Dihydropyrene
• CAS: 28862-02-4
• 化学式: C₁₆H₁₂
• 分子量: 204.271
• InChiKey: JBWYHEWFOLZDIH-UHFFFAOYSA-N

物化性质

• 沸点：
  392.4±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,9-二氢芘 在 盐酸 、 三氯化铝 、 lithium 作用下， 以 四氢呋喃 、 甲醇 、 二硫化碳 、 氨 为溶剂， 反应 2.03h， 生成 2-acetyl-4,5,9,10-tetrahydropyrene
  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：

  芘 在 lithium 作用下， 以 氨 为溶剂， 反应 1.0h， 生成 1,9-二氢芘
  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

• Tintel, C.; Cornelisse, J.; Lugtenburg, J., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 1, p. 14 - 20
  作者：Tintel, C.、Cornelisse, J.、Lugtenburg, J.

  DOI：——

  日期：——
• TINTEL, C.;CORNELISSE, J.;LUGTENBURG, J., REC. TRAV. CHIM. PAYS-BAS, 1983, 102, N 1, 14-19
  作者：TINTEL, C.、CORNELISSE, J.、LUGTENBURG, J.

  DOI：——

  日期：——
• 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.