(Z)-3,4-Dimethyl-5-(3,4-dimethyl-5-formyl-2-pyrrolylmethylen)-3-pyrrolin-2-on | 65113-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3,4-Dimethyl-5-(3,4-dimethyl-5-formyl-2-pyrrolylmethylen)-3-pyrrolin-2-on
• 英文别名: (Z)-3,4-Dimethyl-5-(3,4-dimethyL5-formyl-2-pyrrolylmethylen)-3-pyrrolin-2-on；5-[(Z)-(3,4-dimethyl-5-oxopyrrol-2-ylidene)methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 65113-71-5
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: FVYFHZSRVPORHO-XGICHPGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3,4-Dimethyl-5-(3,4-dimethyl-5-formyl-2-pyrrolylmethylen)-3-pyrrolin-2-on 、 1',3,4-trimethyl-2,2'-pyrromethen-5<1H>-one 在 三氟乙酸 作用下， 反应 72.0h， 以23%的产率得到(4Z,9Z,15Z)-2,3,7,8,17,18,23-heptamethylbilin-1,19-(21H,23H,24H)-dione
  参考文献：
  名称：

  Inducing Geometrical Changes of Biliverdin Chromophores by 23N-Methylation

  摘要：

  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).

  DOI：

  10.1007/s00706-004-0269-4

文献信息

• Inducing anti-Conformers of Biliverdin Chromophores by Reducing Sterical Hindrance
  作者：Martin Hölzl、Alexander Jarosik、Karl Grubmayr

  DOI：10.1007/s00706-004-0268-5

  日期：2005.5

  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.
• Protonated 2,3-Dihydrobilindiones—Models for the Chromophores of Phycocyanin and the Red-Absorbing Form of Phytochrome
  作者：Michael Stanek、Karl Grubmayr

  DOI：10.1002/(sici)1521-3765(19980904)4:9<1653::aid-chem1653>3.0.co;2-k

  日期：1998.9.4

  New structural and thermodynamic data on the protonation of 2,3-dihydrobilindiones are presented with respect to the ionic aspects of the chromophore-protein interactions in biliproteins. When intermolecular protonation with stoichiometric quantities of strong (sulfonic) acids was investigated by NMR spectroscopy, it was found that the positive charge is localized at the nitrogen atom of the azafulvenic ring B moiety. Complete protonation by weaker (carboxylic) acids can be achieved only intramolecularly at low temperature. The (2R,3R,3'R,CysR)-cysteine adduct of phycocyanobilin dimethyl ester was synthesized to mimic the acid-base chemistry between protein and chromophore. Thermodynamic data for the equilibrium between its neutral form 1 and zwitterion 1(+/-) were calculated from the temperature dependence of the visible spectra (Delta H degrees = -20.8 kJ mol(-1) Delta S degrees = -71 J mol(-1) K-1). These data are in accord. with others from intramolecular proton transfers, explaining the perfect order of highly conserved consensus sequences necessary for the effective protonation of the chromophores in various light-harvesting biliproteins such as phycocyanin. On the other hand, the highly negative value of Delta S degrees indicates the possibility of the reprotonation of the protein in case of steric interference. The geometrical changes of the protonated Pr chromophore of phytochrome as a result of the Z-->E photoisomerization may trigger proton transfer back to the protein and thus initiate the sequence of dark reactions that lead to the physiologically active Pfr form of phytochrome.
• On the chemistry of pyrrole pigments, LXXXIX: Vinylogous linear di- and tetrapyrroles
  作者：Heinz Falk、Maria Fr�hwirth

  DOI：10.1007/bf00808284

  日期：1992.12

  A vinylogous dipyrrinone, its Ehrlich aldehyde condensate, and the vinylogous bilindione derived from the vinylogous dipyrrinone were prepared. Their structural aspects of tautomerism, configuration and conformation were derived by analysis of their H-1-NMR data. Selected physical properties were determined and are discussed.
• Beitr�ge zur Chemie der Pyrrolpigmente, 82. Mitt.: Wasserl�sliche Polymere mit kovalent gebundenen violinoiden und 2,3-dihydro-verdinoiden Gallenfarbstoffen
  作者：Heinz Falk、Karl Grubmayr、Martha Marko

  DOI：10.1007/bf00809971

  日期：——