2,2'-diacetoxy-1,1'-binaphthyl-3,3'-bis(ethyne) | 730971-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-diacetoxy-1,1'-binaphthyl-3,3'-bis(ethyne)
• 英文别名: [1-(2-Acetyloxy-3-ethynylnaphthalen-1-yl)-3-ethynylnaphthalen-2-yl] acetate
• CAS: 730971-06-9；680588-10-7
• 化学式: C₂₈H₁₈O₄
• 分子量: 418.449
• InChiKey: NRKSWWLJUNKUFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  顺-二氯双(三乙基膦)铂(II) 、 2,2'-diacetoxy-1,1'-binaphthyl-3,3'-bis(ethyne) 在 copper(l) chloride 作用下， 以91%的产率得到
  参考文献：
  名称：

  Expeditious Assembly of Mesoscopic Metallocycles

  摘要：

  Very large chiral metallocycles with tunable cavities in the range of 0.9-22 nm were efficiently assembled from the requisite metal- and ligand-terminated oligomers that are built from the 2,2'-diacetoxy-1,1'-binaphthyl-3,3'-bis(ethyne) bridging ligand and trans-Pt(PEt3)2 metal connector. These unprecedented nanoscopic and mesoscopic molecular metallocycles have been characterized with 1H, 13C{1H}, and 31P{1H} NMR spectroscopy, microanalysis, IR, UV-vis, and circular dichroism spectroscopies, MALDI-TOF MS, and size exclusion chromatography (SEC). SEC results indicated that the metallocycles appear to be much more compact and rigid than the metal- and ligand-terminated oligomers. The present molecular metallocycles provide interesting building blocks for the construction of larger functional structures that cannot be accessed from a top-down approach.

  DOI：

  10.1021/ja049145m
• 作为产物：
  描述：

  (R)-3,3'-diiodo-[1,1'-binaphthalene]-2,2'-diol 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 97.0h， 生成 2,2'-diacetoxy-1,1'-binaphthyl-3,3'-bis(ethyne)
  参考文献：
  名称：

  Chiral Metallacyclophanes:  Self-Assembly, Characterization, and Application in Asymmetric Catalysis

  摘要：

  A family of chiral metallacyclophanes has been readily assembled based on robust Pt-acetylide linkage and characterized by a variety of spectroscopic techniques and X-ray crystallography. The steric congestion around the chiral dihydroxy groups in rigid metallacyclophane 4 prevents their reactions with Ti((OPr)-Pr-i)(4) to form active catalysts for enantioselective diethylzinc additions to aromatic aldehydes. In contrast, chiral dihydroxy groups in more flexible unclosed metallacyclophane 5 are effective ligands for enantioselective catalytic diethylzinc additions to aromatic aldehydes.

  DOI：

  10.1021/ol036111v