6,6'-dibromo-N,N,N'N'-tetrabutyl-1,1'-binaphthyl-2,2'-diamine | 911295-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,6'-dibromo-N,N,N'N'-tetrabutyl-1,1'-binaphthyl-2,2'-diamine
• 英文别名: (R)-6,6'-dibromo-N,N,N'N'-tetrabutyl-1,1'-binaphthyl-2,2'-diamine
• CAS: 911295-08-4
• 化学式: C₃₆H₄₆Br₂N₂
• 分子量: 666.583
• InChiKey: HLBZLHPIHIGVNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.0
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6,6'-dibromo-N,N,N'N'-tetrabutyl-1,1'-binaphthyl-2,2'-diamine 在 palladium diacetate 三(邻甲基苯基)磷 作用下， 以 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Unique Contrast Patterns from Resonance-Enhanced Chiral SHG of Cell Membranes

  摘要：

  Chirality can produce novel nonlinear optical effects that may form the basis for new imaging contrast agents. In this paper, we developed a new chiral chromophore 2, which is the dimer of a known voltage sensitive dye, monomer 1, with the chirality originating from the twisted orientation between two subunits. Racemic dimer and monomer 1 were used as the references to study the effect of chirality in SHG microscopy of live cells. All these dyes selectively stain the outer leaflets of cell membranes, producing strong resonance-enhanced SHG images. At the symmetric junction between two adherent cells, monomer or racemic dimer SHG is forbidden due to centrosymmetry, and indeed little SHG was observed (10 +/- 1% relative to nonjunction). When stained with the chiral dimer, the junction is no longer centrosymmetric and much stronger SHG was observed (39 +/- 4% relative to nonjunction). Plane polarized light produces highly polarized images of spherical cells stained with racemic dye, but for the chiral dye, the polarized pattern is largely eliminated by the chiral SHG emanating from the subresolution membrane convolutions.

  DOI：

  10.1021/ja0635534
• 作为产物：
  描述：

  [1,1’-联萘]-2,2’-二胺 在 硫酸 、 溴 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 6,6'-dibromo-N,N,N'N'-tetrabutyl-1,1'-binaphthyl-2,2'-diamine
  参考文献：
  名称：

  Unique Contrast Patterns from Resonance-Enhanced Chiral SHG of Cell Membranes

  摘要：

  Chirality can produce novel nonlinear optical effects that may form the basis for new imaging contrast agents. In this paper, we developed a new chiral chromophore 2, which is the dimer of a known voltage sensitive dye, monomer 1, with the chirality originating from the twisted orientation between two subunits. Racemic dimer and monomer 1 were used as the references to study the effect of chirality in SHG microscopy of live cells. All these dyes selectively stain the outer leaflets of cell membranes, producing strong resonance-enhanced SHG images. At the symmetric junction between two adherent cells, monomer or racemic dimer SHG is forbidden due to centrosymmetry, and indeed little SHG was observed (10 +/- 1% relative to nonjunction). When stained with the chiral dimer, the junction is no longer centrosymmetric and much stronger SHG was observed (39 +/- 4% relative to nonjunction). Plane polarized light produces highly polarized images of spherical cells stained with racemic dye, but for the chiral dye, the polarized pattern is largely eliminated by the chiral SHG emanating from the subresolution membrane convolutions.

  DOI：

  10.1021/ja0635534