[5]helicene-5,10-dicarboxylic acid | 1604047-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: [5]helicene-5,10-dicarboxylic acid
• 英文别名: Pentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(14),2(11),3,5,7,9,12,15,17,19,21-undecaene-9,16-dicarboxylic acid；pentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(14),2(11),3,5,7,9,12,15,17,19,21-undecaene-9,16-dicarboxylic acid
• CAS: 1604047-45-1
• 化学式: C₂₄H₁₄O₄
• 分子量: 366.373
• InChiKey: SVVBDHQDLRGCQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [5]helicene-5,10-dicarboxylic acid 在 硫酸 、 碘 作用下， 以 甲苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Facile Photochemical Synthesis of 5,10-Disubstituted [5]Helicenes by Removing Molecular Orbital Degeneracy

  摘要：

  Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [S]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C-2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.

  DOI：

  10.1021/ol5008718
• 作为产物：
  描述：

  对苯二甲醛 在 sodium ethanolate 、 potassium hydroxide 作用下， 以 乙醇 、 乙二醇甲醚 、 水 为溶剂， 反应 92.0h， 生成 [5]helicene-5,10-dicarboxylic acid
  参考文献：
  名称：

  Facile Photochemical Synthesis of 5,10-Disubstituted [5]Helicenes by Removing Molecular Orbital Degeneracy

  摘要：

  Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [S]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C-2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.

  DOI：

  10.1021/ol5008718

文献信息

• Facile Photochemical Synthesis of 5,10-Disubstituted [5]Helicenes by Removing Molecular Orbital Degeneracy
  作者：Natsuki Ito、Takashi Hirose、Kenji Matsuda

  DOI：10.1021/ol5008718

  日期：2014.5.2

  Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [S]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C-2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.