(2,3''-Bis-tert-butoxycarbonylmethoxy-4''-iodo-[1,1';4',1'']terphenyl-2'-yloxy)-acetic acid tert-butyl ester | 678988-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,3''-Bis-tert-butoxycarbonylmethoxy-4''-iodo-[1,1';4',1'']terphenyl-2'-yloxy)-acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-[2-[4-[4-iodo-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]phenoxy]acetate
• CAS: 678988-86-8
• 化学式: C₃₆H₄₃IO₉
• 分子量: 746.637
• InChiKey: NYYQVAGMQNZLPW-UHFFFAOYSA-N

物化性质

• 熔点：
  42.0-43.0 °C
• 沸点：
  684.1±55.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  频那醇硼烷 、 (2,3''-Bis-tert-butoxycarbonylmethoxy-4''-iodo-[1,1';4',1'']terphenyl-2'-yloxy)-acetic acid tert-butyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 [2,2'-Bis-tert-butoxycarbonylmethoxy-4''-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-[1,1';4',1'']terphenyl-3''-yloxy]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of {323}-p-Octiphenyls:  Orthogonal Functionalization along a Rigid-Rod Scaffold for Refined Supramolecular Architecture

  摘要：

  The synthesis of p-octiphenyls carrying orthogonal tert-butyl esters in the peripheral positions 12, 22, 33, 62, 73, and 82 and either p-methoxybenzyl or benzyl ester substituents in the central positions 42 and 53 is described. Resolution-enhanced HSQC/HMBC two-dimensional NMR spectroscopy is implemented as an attractive method for the complete characterization of complex p-oligophenyl scaffolds.

  DOI：

  10.1021/ol036363w
• 作为产物：
  描述：

  2-甲氧基苯基硼酸 在 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 、 caesium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 25.0h， 生成 (2,3''-Bis-tert-butoxycarbonylmethoxy-4''-iodo-[1,1';4',1'']terphenyl-2'-yloxy)-acetic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of {323}-p-Octiphenyls:  Orthogonal Functionalization along a Rigid-Rod Scaffold for Refined Supramolecular Architecture

  摘要：

  The synthesis of p-octiphenyls carrying orthogonal tert-butyl esters in the peripheral positions 12, 22, 33, 62, 73, and 82 and either p-methoxybenzyl or benzyl ester substituents in the central positions 42 and 53 is described. Resolution-enhanced HSQC/HMBC two-dimensional NMR spectroscopy is implemented as an attractive method for the complete characterization of complex p-oligophenyl scaffolds.

  DOI：

  10.1021/ol036363w

文献信息

• Zipper Assembly of Photoactive Rigid-Rod Naphthalenediimide π-Stack Architectures on Gold Nanoparticles and Gold Electrodes
  作者：Naomi Sakai、Adam L. Sisson、Thomas Bürgi、Stefan Matile

  DOI：10.1021/ja077099v

  日期：2007.12.1

  We introduce zipper assembly as a simple and general concept to create complex functional architectures an conducting surfaces. Rigid-rod pi-stack architecture composed of p-oligophenyl rods and blue naphthalenediimide (NDI) stacks is selected as an example. First, short p-quaterphenyl initiators with four anionic NDIs are deposited on gold. Then, long p-octiphenyl propagators with eight cationic NDIs are added. The lower half of the propagator pi-stacks with the initiator, whereas the upper half of the molecule remains free. These cationic sticky-ends zip up with anionic propagators to produce anionic sticky-ends, and so on. Zipper assembly on gold nanoparticles is demonstrated by the appearance of the absorption of face-to-face NDI pi-stacks and the shift of the surface plasmon resonance band with increasing layer thickness. Complete inhibition by zipper capping demonstrates that zipper assembly affords complex architectures that are more ordered than those obtained by conventional layer-by-layer (LBL) approaches. Zipper assembly on gold electrodes produces increasing photocurrents with increasing number of zipped layers. The photocurrents obtained by this method are much higher than those obtained by conventional LBL controls; zipper termination by capping cleanly stops any increase in photocurrent.