5-[4-(4-ethynylphenylethynyl)phenyl]-1,2,5-dithiazepane | 476182-65-7

• 分子结构分类: 有机化合物
• 英文名称: 5-[4-(4-ethynylphenylethynyl)phenyl]-1,2,5-dithiazepane
• 英文别名: 5-[4-[2-(4-Ethynylphenyl)ethynyl]phenyl]-1,2,5-dithiazepane
• CAS: 476182-65-7
• 化学式: C₂₀H₁₇NS₂
• 分子量: 335.494
• InChiKey: KZCKIJJJKFPFTR-UHFFFAOYSA-N

物化性质

• 沸点：
  519.3±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[4-(4-ethynylphenylethynyl)phenyl]-1,2,5-dithiazepane 、 4-[4-[3,5,7-tris(4-iodophenyl)adamantan-1-yl]phenylethynyl]benzoic acid methyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以8%的产率得到4-[4-[3,5,7-tris[4-[4-[4-(1,2,5-dithiazepan-5-yl)phenylethynyl]phenylethynyl]phenyl]adamantan-1-yl]phenylethynyl]benzoic acid methyl ester
  参考文献：
  名称：

  Nanoscale Tripodal 1,3,5,7-Tetrasubstituted Adamantanes for AFM Applications

  摘要：

  The synthesis of four novel nanoseale 1,3,5,7-tetrasubstituted adamantanes 22 and 25-27 designed for atomic force microscopy (AFM) applications is described. Each tetrahedrally shaped molecule incorporates a broad tripodal base made up of three identical legs that terminate with a sulfurcontaining moiety, which is either a 4-acetylsulfanylmethylphenyl unit or else a (1,2,5-dithiazepan1-yl)phenyl unit. The sulfur atoms are intended for eventual binding of the molecule multivalently to the apex of a gold-coated commercial AFM tip through formation of multiple S-Au bonds. In each molecule, the fourth terminus is a para-substituted benzoic acid methyl ester that is designed to scan the sample. We demonstrate that 27 is sufficiently large and rigid to be imaged by a conventional AFM tip. Adamantanes 22 and 25-27 may also find application as chemically well-defined nanoscale objects for calibration of AFM tips.

  DOI：

  10.1021/jo026923p
• 作为产物：
  描述：

  5-(4-trimethylsilanylethynylphenyl)-[1,2,5]dithiazepane 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 19.5h， 生成 5-[4-(4-ethynylphenylethynyl)phenyl]-1,2,5-dithiazepane
  参考文献：
  名称：

  Nanoscale 1,3,5,7-Tetrasubstituted Adamantanes and p-Substituted Tetraphenyl-methanes for AFM Applications

  摘要：

  [GRAPHICS]Tetrahedrally shaped nanoscale molecules 18-20 were synthesized from the corresponding tetraiodide by a series of Sonogashira coupling reactions. Three of the sulfur-containing termini are intended for eventual binding to a gold-coated conventional AFM tip, while the fourth terminus scans the sample. AFM images of 19 demonstrate that the molecule is sufficiently large and rigid to be imaged by a conventional AFM tip.

  DOI：

  10.1021/ol026495+