4-[4-[3,5,7-tris(4-iodophenyl)adamantan-1-yl]phenylethynyl]benzoic acid methyl ester | 562823-77-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-[4-[3,5,7-tris(4-iodophenyl)adamantan-1-yl]phenylethynyl]benzoic acid methyl ester
• 英文别名: Methyl 4-[2-[4-[3,5,7-tris(4-iodophenyl)-1-adamantyl]phenyl]ethynyl]benzoate
• CAS: 562823-77-2
• 化学式: C₄₄H₃₅I₃O₂
• 分子量: 976.474
• InChiKey: CPLGCXMFWZIZRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  49
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(S-acetylthiomethyl)phenyl]acetylene 、 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19%的产率得到4-[4-[3,5,7-tris[4-(4-acetylsulfanylmethylphenylethynyl)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：

  4-碘苯甲酸 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 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 4-[4-[3,5,7-tris(4-iodophenyl)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