1-[6-(4-Propylsulfanyl-6-{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}-pyridin-2-yl)-pyrimidin-4-yl]-ethanone | 257957-55-4

• 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-(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}-pyridin-2-yl)-pyrimidin-4-yl]-ethanone
• CAS: 257957-55-4
• 化学式: C₅₅H₅₁N₁₃OS₄
• 分子量: 1038.36
• InChiKey: RQQBVNDFCSLWTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.37
• 重原子数：
  73.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  184.64
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  1-[6-[6-[6-(1-Ethoxyethenyl)pyrimidin-4-yl]-4-propylsulfanylpyridin-2-yl]pyrimidin-4-yl]-3,3-bis(propylsulfanyl)prop-2-en-1-one 、 1-[6-(4-Propylsulfanyl-6-{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}-pyridin-2-yl)-pyrimidin-4-yl]-ethanone 在 18-冠醚-6 、 potassium tert-butylate 、 ammonium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以27%的产率得到
  参考文献：
  名称：

  Helicity Coding: Programmed Molecular Self-Organization of Achiral Nonbiological Strands into Multiturn Helical Superstructures: Synthesis and Characterization of Alternating Pyridine-Pyrimidine Oligomers

  摘要：

  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.

  DOI：

  10.1002/(sici)1521-3765(19991203)5:12<3471::aid-chem3471>3.0.co;2-5
• 作为产物：
  描述：

  6-[6-(6-{6-[6-(6-{6-[6-(1-Ethoxy-vinyl)-pyrimidin-4-yl]-4-propylsulfanyl-pyridin-2-yl}-pyrimidin-4-yl)-4-propylsulfanyl-pyridin-2-yl]-pyrimidin-4-yl}-4-propylsulfanyl-pyridin-2-yl)-pyrimidin-4-yl]-4-propylsulfanyl-[2,2']bipyridinyl 在 盐酸 、 水 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 1.0h， 以93%的产率得到1-[6-(4-Propylsulfanyl-6-{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}-pyridin-2-yl)-pyrimidin-4-yl]-ethanone
  参考文献：
  名称：

  Helicity Coding: Programmed Molecular Self-Organization of Achiral Nonbiological Strands into Multiturn Helical Superstructures: Synthesis and Characterization of Alternating Pyridine-Pyrimidine Oligomers

  摘要：

  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.

  DOI：

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