5-(4-ethynylphenyl)-1,2,5-dithiazepane | 476182-61-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(4-ethynylphenyl)-1,2,5-dithiazepane
• CAS: 476182-61-3
• 化学式: C₁₂H₁₃NS₂
• 分子量: 235.374
• InChiKey: CCBNMFYYBDVKJM-UHFFFAOYSA-N

物化性质

• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-ethynylphenyl)-1,2,5-dithiazepane 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 19.0h， 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+
• 作为产物：
  描述：

  N,N-bis(2-chloroethyl)-4-iodoaniline 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 potassium thioacyanate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 60.5h， 生成 5-(4-ethynylphenyl)-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+

文献信息

• Nanoscale Tripodal 1,3,5,7-Tetrasubstituted Adamantanes for AFM Applications
  作者：Quan Li、Aleksey V. Rukavishnikov、Pavel A. Petukhov、Tatiana O. Zaikova、Changshu Jin、John F. W. Keana

  DOI：10.1021/jo026923p

  日期：2003.6.1

  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.