S(a)-2,2'-diethoxy-1,1'-binaphthalene-6,6'-bis(4-vinylpyridine)

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S(a)-2,2'-diethoxy-1,1'-binaphthalene-6,6'-bis(4-vinylpyridine)
• 英文别名: (S)-2,2'-diethoxy-1,1'-binaphthyl-6,6'-bis(4-vinylpyridine)；4-[(E)-2-[6-ethoxy-5-[2-ethoxy-6-[(E)-2-pyridin-4-ylethenyl]naphthalen-1-yl]naphthalen-2-yl]ethenyl]pyridine
• 化学式: C₃₈H₃₂N₂O₂
• 分子量: 548.684
• InChiKey: ZHWXRPNPDHPYDP-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(η⁵-pentamethyl-cyclopentadienyl)₂Ir₂(2,5-dihydroxy-1,4-benzoquinone)(OTf)₂] 、 S(a)-2,2'-diethoxy-1,1'-binaphthalene-6,6'-bis(4-vinylpyridine) 以 甲醇 为溶剂， 以38 mg的产率得到4C₃₈H₃₂N₂O₂*8C₁₀H₁₅^(1-)*8Ir⁽³⁺⁾*8CF₃O₃S^(1-)*4C₆H₂O₄^(2-)
  参考文献：
  名称：

  拓扑手性所罗门链接的立体选择性合成

  摘要：

  在逆合成分析的帮助下，我们利用轴向手性配体的配位驱动自组装和手性诱导，实现了备受期待的拓扑手性所罗门链接的立体选择性合成。配体 (R or S)-2,2'-diethoxy-1,1'-binaphthyl-6,6'-bis(4-vinylpyridine) (RL or SL) 与双核铱络合物 [Cp*2Ir2( DHBQ)(OTf)2] (Ir-B(OTf)2, H2DHBQ = 2,5-dihydroxy-1,4-benzoquinone) 允许非对映选择性合成拓扑对映异构体 P (Ir-1P) 或 M (Ir-1M)所罗门链接，分别。形成所罗门键的主要驱动力是手性配体之间的 π-π 相互作用。

  DOI：

  10.1021/jacs.0c05366
• 作为产物：
  描述：

  4-乙烯基吡啶 、 (R)-6,6'-dibromo-2,2'-diethoxy-1,1'-binaphthyl 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以94%的产率得到S(a)-2,2'-diethoxy-1,1'-binaphthalene-6,6'-bis(4-vinylpyridine)
  参考文献：
  名称：

  Interlocked Chiral Nanotubes Assembled from Quintuple Helices

  摘要：

  Homochiral helical chains were rationally synthesized from C2-symmetric 1,1-binaphthyl-6,6'-bipyridine ligands and linear metal-connecting points, Ni(acac)2. Five such homochiral helices associate in parallel to form nanotubes of 2 x 2 nm in dimensions which further intertwine to form periodically ordered, interlocked nanotubular architectures that possess nanometer-scale open channels and have high affinity for aromatic molecules. Chiral crown ethers have also been successfully incorporated into the walls of these nanotubes, which promises to lead to novel chiral zeolitic materials applicable in enantioselective processes.

  DOI：

  10.1021/ja029926s

文献信息

• Homochiral porous solids based on 1D coordination polymers built from 46-membered macrocycles
  作者：Chuan-De Wu、Wenbin Lin

  DOI：10.1039/b606817k

  日期：——

  Six homochiral coordination polymers 1–6 based on an enantiopure elongated and bent bipyridine ligand were synthesized and characterized by single-crystal X-ray diffraction studies. The framework structures of all six compounds were built up from similar 1D polymeric chains composed of 46-membered metallomacrocycles. Four distinct packing patterns were observed for this family of coordination polymers. With the exception of 1, the anions do not coordinate to the metal centers and reside in the open channels. Single-crystal X-ray diffraction studies show that the structures of these coordination polymers are sensitive to the anions even though they do not coordinate to the metal centers. The framework structures are somewhat tolerant of the change of metal centers and their local coordination environments. Gas sorption measurements on 1 suggest that chiral porous solids can be obtained with the present 1D coordination polymeric building blocks.

  合成了六种基于对映纯拉长且弯曲的联吡啶配体的纯手性配位聚合物 1-6，并通过单晶 X 射线衍射研究进行了表征。所有六种化合物的骨架结构均由相似的由 46 元金属大环组成的一维聚合物链构建而成。对于该配位聚合物家族，观察到四种不同的堆积模式。除 1 外，阴离子不与金属中心配位并驻留在开放通道中。单晶 X 射线衍射研究表明，这些配位聚合物的结构对阴离子敏感，即使它们不与金属中心配位。框架结构对金属中心及其局部协调环境的变化有一定的容忍度。 1 上的气体吸附测量表明，可以使用现有的一维配位聚合物构件获得手性多孔固体。
• Interlocked Chiral Nanotubes Assembled from Quintuple Helices
  作者：Yong Cui、Suk Joong Lee、Wenbin Lin

  DOI：10.1021/ja029926s

  日期：2003.5.1

  Homochiral helical chains were rationally synthesized from C2-symmetric 1,1-binaphthyl-6,6'-bipyridine ligands and linear metal-connecting points, Ni(acac)2. Five such homochiral helices associate in parallel to form nanotubes of 2 x 2 nm in dimensions which further intertwine to form periodically ordered, interlocked nanotubular architectures that possess nanometer-scale open channels and have high affinity for aromatic molecules. Chiral crown ethers have also been successfully incorporated into the walls of these nanotubes, which promises to lead to novel chiral zeolitic materials applicable in enantioselective processes.
• Stereoselective Synthesis of a Topologically Chiral Solomon Link
  作者：Zheng Cui、Ye Lu、Xiang Gao、Hui-Jun Feng、Guo-Xin Jin

  DOI：10.1021/jacs.0c05366

  日期：2020.8.12

  With the help of retrosynthetic analysis, we have realized the highly anticipated stereoselective synthesis of a topologically chiral Solomon link, by taking advantage of coordination-driven self-assembly and chiral induction by axially chiral ligands. Combination of the ligands (R or S)-2,2'-diethoxy-1,1'-binaphthyl-6,6'-bis(4-vinylpyridine) (R-L or S-L) with the binuclear iridium complex [Cp*2Ir2(DHBQ)(OTf)2]

  在逆合成分析的帮助下，我们利用轴向手性配体的配位驱动自组装和手性诱导，实现了备受期待的拓扑手性所罗门链接的立体选择性合成。配体 (R or S)-2,2'-diethoxy-1,1'-binaphthyl-6,6'-bis(4-vinylpyridine) (RL or SL) 与双核铱络合物 [Cp*2Ir2( DHBQ)(OTf)2] (Ir-B(OTf)2, H2DHBQ = 2,5-dihydroxy-1,4-benzoquinone) 允许非对映选择性合成拓扑对映异构体 P (Ir-1P) 或 M (Ir-1M)所罗门链接，分别。形成所罗门键的主要驱动力是手性配体之间的 π-π 相互作用。