(R)-6,6'-diethynyl-2,2'-bis[(4-piperidinophenyl)ethynyl]-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-6,6'-diethynyl-2,2'-bis[(4-piperidinophenyl)ethynyl]-1,1'-binaphthyl
• 英文别名: 1-[4-[2-[6-Ethynyl-1-[6-ethynyl-2-[2-(4-piperidin-1-ylphenyl)ethynyl]naphthalen-1-yl]naphthalen-2-yl]ethynyl]phenyl]piperidine；1-[4-[2-[6-ethynyl-1-[6-ethynyl-2-[2-(4-piperidin-1-ylphenyl)ethynyl]naphthalen-1-yl]naphthalen-2-yl]ethynyl]phenyl]piperidine
• 化学式: C₅₀H₄₀N₂
• 分子量: 668.881
• InChiKey: KRWKOECKXQEUBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  52
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-硝基碘苯 、 (R)-6,6'-diethynyl-2,2'-bis[(4-piperidinophenyl)ethynyl]-1,1'-binaphthyl 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到(R)-6,6'-bis[(4-nitrophenyl)ethynyl]-2,2'-bis[(4-piperidinophenyl)ethynyl]-1,1'-binaphthyl
  参考文献：
  名称：

  Potential 1,1′-binaphthyl NLO-phores with extended conjugation between positions 2 and 6, and 2′ and 6′

  摘要：

  A synthetic approach is reported which allows independent introduction of alkynyl groups to positions 2,20 and then to 6,6' of binaphthyls. The approach is based on the high selectivity of the Stephens-Castro alkynylation of 6,6'-dibromo-2,2'-diiodo-1,1'- binaphthyl. The tetraalkynylated derivatives exhibit extended conjugation between groups at positions 2 and 6, and 20 and 60, achieved by overcoming steric hindrance at positions 2 and 2' by using alkynyl spacers. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.044
• 作为产物：
  描述：

  (R)-2,2'-bis[(4-piperidinophenyl)ethynyl]-6,6'-bis(trimethylsilylethynyl)-1,1'-binaphthyl 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(R)-6,6'-diethynyl-2,2'-bis[(4-piperidinophenyl)ethynyl]-1,1'-binaphthyl
  参考文献：
  名称：

  Potential 1,1′-binaphthyl NLO-phores with extended conjugation between positions 2 and 6, and 2′ and 6′

  摘要：

  A synthetic approach is reported which allows independent introduction of alkynyl groups to positions 2,20 and then to 6,6' of binaphthyls. The approach is based on the high selectivity of the Stephens-Castro alkynylation of 6,6'-dibromo-2,2'-diiodo-1,1'- binaphthyl. The tetraalkynylated derivatives exhibit extended conjugation between groups at positions 2 and 6, and 20 and 60, achieved by overcoming steric hindrance at positions 2 and 2' by using alkynyl spacers. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.044

文献信息

• Potential 1,1′-binaphthyl NLO-phores with extended conjugation between positions 2 and 6, and 2′ and 6′
  作者：Michal Juríček、Peter Kasák、Marek Stach、Martin Putala

  DOI：10.1016/j.tetlet.2007.10.044

  日期：2007.12

  A synthetic approach is reported which allows independent introduction of alkynyl groups to positions 2,20 and then to 6,6' of binaphthyls. The approach is based on the high selectivity of the Stephens-Castro alkynylation of 6,6'-dibromo-2,2'-diiodo-1,1'- binaphthyl. The tetraalkynylated derivatives exhibit extended conjugation between groups at positions 2 and 6, and 20 and 60, achieved by overcoming steric hindrance at positions 2 and 2' by using alkynyl spacers. (C) 2007 Elsevier Ltd. All rights reserved.