(4Z)-2,3,7,9-tetramethyldipyrrin-1(10H)-one | 868829-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (4Z)-2,3,7,9-tetramethyldipyrrin-1(10H)-one
• CAS: 868829-18-9
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: GCBDUBBOSLBDGO-SDQBBNPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.89
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4Z)-2,3,7,9-tetramethyldipyrrin-1(10H)-one 、 (4Z)-2,3,7,8-tetramethyl-10H-dipyrrin-1-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以17%的产率得到(4Z,9Z,15Z)-2,3,7,8,13,17,18-heptamethylbilin-1,19-(21H,24H)-dione
  参考文献：
  名称：

  Inducing anti-Conformers of Biliverdin Chromophores by Reducing Sterical Hindrance

  摘要：

  Two different types of conformational changes of the biliverdin chromophore were accomplished by the concept of reducing sterical hindrance. On one hand, model compounds unsubstituted at position 7 and/or 13 adopt the semi-extended geometry with anti-conformation of the dipyrrinone moiety. On the other hand, stretching of the chromophore with anti-conformation of the dipyrrin substructure was achieved with a model compound unsubstituted at position 12. Both kinds of anti-conformations have been proved by 2D NMR and UV-Vis spectroscopy.

  DOI：

  10.1007/s00706-004-0268-5
• 作为产物：
  描述：

  3,4-dimethyl-3-pyrrolin-2-one 、 3,5-二甲基-2-吡咯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以46%的产率得到(4Z)-2,3,7,9-tetramethyldipyrrin-1(10H)-one
  参考文献：
  名称：

  Inducing anti-Conformers of Biliverdin Chromophores by Reducing Sterical Hindrance

  摘要：

  Two different types of conformational changes of the biliverdin chromophore were accomplished by the concept of reducing sterical hindrance. On one hand, model compounds unsubstituted at position 7 and/or 13 adopt the semi-extended geometry with anti-conformation of the dipyrrinone moiety. On the other hand, stretching of the chromophore with anti-conformation of the dipyrrin substructure was achieved with a model compound unsubstituted at position 12. Both kinds of anti-conformations have been proved by 2D NMR and UV-Vis spectroscopy.

  DOI：

  10.1007/s00706-004-0268-5

文献信息

• Inducing Geometrical Changes of Biliverdin Chromophores by 23N-Methylation
  作者：Martin Hölzl、Christian Klampfl、Karl Grubmayr

  DOI：10.1007/s00706-004-0269-4

  日期：2005.5

  Transfer of sterical hindrance from the periphery to the center of biliverdins by placing a methyl group at N23 and hydrogens at the beta-carbons in position 12 and 13 changes the conformation of the chromophore from (10syn, 4syn) to (10anti,14anti). Additional reduction of sterical hindrance by placing a further hydrogen at the beta-carbon in position 8 induces a change in configuration from (9Z) to (9E).