1-[6-[4-Propylsulfanyl-6-[6-(4-propylsulfanyl-6-pyridin-2-ylpyridin-2-yl)pyrimidin-4-yl]pyridin-2-yl]pyrimidin-4-yl]ethanone | 197434-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-[6-[4-Propylsulfanyl-6-[6-(4-propylsulfanyl-6-pyridin-2-ylpyridin-2-yl)pyrimidin-4-yl]pyridin-2-yl]pyrimidin-4-yl]ethanone
• CAS: 197434-25-6
• 化学式: C₃₁H₂₉N₇OS₂
• 分子量: 579.75
• InChiKey: WHOGXIRZUGCVSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-[6-[4-Propylsulfanyl-6-[6-(4-propylsulfanyl-6-pyridin-2-ylpyridin-2-yl)pyrimidin-4-yl]pyridin-2-yl]pyrimidin-4-yl]ethanone 、 3,3-Bis-propylsulfanyl-1-{6-[4-propylsulfanyl-6-(6-{4-propylsulfanyl-6-[6-(4-propylsulfanyl-[2,2']bipyridinyl-6-yl)-pyrimidin-4-yl]-pyridin-2-yl}-pyrimidin-4-yl)-pyridin-2-yl]-pyrimidin-4-yl}-propenone 在 potassium tert-butylate 、 ammonium acetate 作用下， 生成 4,6-bis-{4-n-propylthio-6-[4-(4-n-propylthio-6-{4-[4-n-propylthio-6-(pyrid-2-yl)pyrid-2-yl]pyrimid-4-yl}pyrid-6-yl)pyrimid-4-yl]pyrid-2-yl}pyrimidine
  参考文献：
  名称：

  Designed Self-Generation of an Extended Helical Structure From an Achiral Polyheterocylic Strand

  摘要：

  DOI：

  10.1002/anie.199718451
• 作为产物：
  描述：

  1-(6-chloropyrimidin-4-yl)ethanone 在 trans-bis(triphenylphosphine)palladium(II) chloride 乙酸铵 、 盐酸 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 1-[6-[4-Propylsulfanyl-6-[6-(4-propylsulfanyl-6-pyridin-2-ylpyridin-2-yl)pyrimidin-4-yl]pyridin-2-yl]pyrimidin-4-yl]ethanone
  参考文献：
  名称：

  Bassani, Dario M.; Lehn, Jean-Marie, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 10,11, p. 897 - 906

  摘要：

  DOI：

文献信息

• Helicity Coding: Programmed Molecular Self-Organization of Achiral Nonbiological Strands into Multiturn Helical Superstructures: Synthesis and Characterization of Alternating Pyridine-Pyrimidine Oligomers
  作者：Masakazu Ohkita、Jean-Marie Lehn、Gerhard Baum、Dieter Fenske

  DOI：10.1002/(sici)1521-3765(19991203)5:12<3471::aid-chem3471>3.0.co;2-5

  日期：1999.12.3

  Alternating pyridine-pyrimidine oligomers 1, 2, and 3, composed of nineteen, twenty one, and twenty seven heterocycles, respectively, have been synthesized in stepwise fashion and characterized. Examination of their H-1 NMR spectra revealed that these achiral nonbiological oligomers organize spontaneously into multiturn helical structures 1A-3A in solution, as indicated by marked upfield shifts of the aromatic protons coupled with distinct NOE effects. In view of their potential electron-acceptor properties compounds 1-3 also represent coiled wires of nanometric lengths, up to about 90 Angstrom for 3 in its extended form. The helical structure has been confirmed for 1 in the solid state by X-ray crystallography; a chiral channel arrangement involving only one helical enantiomer was found despite of the lack of chiral center in the strand. The oligomers exhibit a broad structureless fluorescence with a large Stokes shift, attributable to intramolecular pyridine excimer emission resulting from the helical ordering. Variable-temperature H-1 NMR experiments revealed that the oligomers exist as equilibrating mixtures of right-handed and left-handed helices. The barrier for helical handedness reversal was found to be independent on the length of the strand; two- (6), three- (1), and four-turn (3) helices showed comparable free energies of activation. Based on these observations, a stepwise folding mechanism involving two perpendicularly twisted pyridine-pyrimidine units in the transition states may be proposed for the helicity inversion processes. The present results together with earlier work indicate that the pyridine-pyrimidine sequence may be considered as a helicity codon, enforcing the formation of helical structures on the basis of: intramolecular structural information.