1-[6-[3,3-Bis(propylsulfanyl)prop-2-enoyl]pyrimidin-4-yl]-3,3-bis(propylsulfanyl)prop-2-en-1-one | 197434-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[6-[3,3-Bis(propylsulfanyl)prop-2-enoyl]pyrimidin-4-yl]-3,3-bis(propylsulfanyl)prop-2-en-1-one
• CAS: 197434-21-2
• 化学式: C₂₂H₃₂N₂O₂S₄
• 分子量: 484.772
• InChiKey: BZMBBZUTBBDTNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[6-[3,3-Bis(propylsulfanyl)prop-2-enoyl]pyrimidin-4-yl]-3,3-bis(propylsulfanyl)prop-2-en-1-one 在 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 为溶剂， 反应 37.0h， 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：
• 作为产物：
  描述：

  1-碘代丙烷 、 1,1'-(4,6-嘧啶二基)二乙酮 在 二硫化碳 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以62%的产率得到1-[6-[3,3-Bis(propylsulfanyl)prop-2-enoyl]pyrimidin-4-yl]-3,3-bis(propylsulfanyl)prop-2-en-1-one
  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

• Dynamic Chemical Devices: Generation of Reversible Extension/Contraction Molecular Motion by Ion-Triggered Single/Double Helix Interconversion
  作者：Mihail Barboiu、Gavin Vaughan、Nathalie Kyritsakas、Jean-Marie Lehn

  DOI：10.1002/chem.200390085

  日期：2003.2.3

  The polyheterocyclic strands 1-H and 2-H adopt a helical shape enforced by the pyridine-pyrimidine helicity codon. The crystal structure of 2-H shows the formation of stacks of dimers of right- and left-handed individual helices. Treatment of 1-H and 2-H with silver triflate results in the generation of double-helical entities 1-DH and 2-DH, containing two strands and two silver ions. NMR studies and

  多杂环链1-H和2-H采用由吡啶-嘧啶的螺旋密码子增强的螺旋形状。2-H的晶体结构显示出右手和左手单个螺旋的二聚体的堆叠。用三氟甲磺酸银处理1-H和2-H导致生成包含两个链和两个银离子的双螺旋实体1-DH和2-DH。NMR研究和2-DH晶体结构的确定表明，通过将每个Ag（+）离子与两个末端联吡啶单元（每个链中的一个）配位，并且通过内部杂环之间明显的pi-pi堆积相互作用，双链体得以稳定股，产生非常坚固的双螺旋结构。单螺旋和双螺旋的可逆互变可以通过添加能够螯合Ag（+）并通过质子化释放的cryptand来实现。因此，连续添加酸和碱会导致较短的（大约3.6 A）单螺旋和较长的（大约10.3 A）双螺旋之间可逆的相互转化，从而导致产生明显的伸展/收缩运动。系统1,2-H / 1,2-DH代表一种动态化学装置，该装置经历了由酸/碱中和作用推动的可逆分子机械运动的离子调制。导致产生明显的伸展/收缩运动。系统1
• Designed Self-Generation of an Extended Helical Structure From an Achiral Polyheterocylic Strand
  作者：Dario M. Bassani、Jean-Marie Lehn、Gerhard Baum、Dieter Fenske

  DOI：10.1002/anie.199718451

  日期：1997.9.17
• 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.