2-[4-[2-(2-Prop-2-enoxyethoxy)ethoxy]phenyl]-9-[3-[9-[4-[2-(2-prop-2-enoxyethoxy)ethoxy]phenyl]-1,10-phenanthrolin-2-yl]phenyl]-1,10-phenanthroline | 199681-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[4-[2-(2-Prop-2-enoxyethoxy)ethoxy]phenyl]-9-[3-[9-[4-[2-(2-prop-2-enoxyethoxy)ethoxy]phenyl]-1,10-phenanthrolin-2-yl]phenyl]-1,10-phenanthroline
• CAS: 199681-56-6
• 化学式: C₅₆H₅₀N₄O₆
• 分子量: 875.036
• InChiKey: RUPPOEDKQWHDRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  66
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  copper(I) hexafluorophosphate 、 2-[4-[2-(2-Prop-2-enoxyethoxy)ethoxy]phenyl]-9-[3-[9-[4-[2-(2-prop-2-enoxyethoxy)ethoxy]phenyl]-1,10-phenanthrolin-2-yl]phenyl]-1,10-phenanthroline 以 二氯甲烷 、 乙腈 为溶剂， 以>99的产率得到
  参考文献：
  名称：

  Copper(I)- or Iron(II)-Templated Synthesis of Molecular Knots Containing Two Tetrahedral or Octahedral Coordination Sites

  摘要：

  Molecular trefoil knots have been prepared from metal-assembled precursors using the ring closing metathesis (RCM) cyclization methodology. The templating metal is either copper(I) or iron(II) and the coordinating fragments 1,10-phenanthroline or 2,2':6',2 "-terpyridine, respectively. The RCM approach, newly applied to the field of catenanes and knots, represents a spectacular synthetic improvement in terms of yield and experimental conditions (no high dilution required). The dicopper(I) trefoil knot has been synthesized in a 74% yield. A similar approach also led to the first knot constructed around two iron(II) bis(terpyridine) moieties, demonstrating that iron(II) can also be used as a highly efficient template. Moreover, for both Cu(I) and Fe(II) knots, it has been possible to quantitatively reduce the cyclic olefins formed during the macrocyclization by catalytic (Pd/C) hydrogenation. An X-ray structure of the double helix of iron(II) bis(1,2-bis(5-(5 "-methyl-2,2':6',2 "-terpyridinyl))ethane) is given which shows that the double-stranded helical precursor is well predisposed for the formation of a molecular knot.

  DOI：

  10.1021/ja982239+
• 作为产物：
  描述：

  3-溴丙烯 、 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-[4-[2-(2-Prop-2-enoxyethoxy)ethoxy]phenyl]-9-[3-[9-[4-[2-(2-prop-2-enoxyethoxy)ethoxy]phenyl]-1,10-phenanthrolin-2-yl]phenyl]-1,10-phenanthroline
  参考文献：
  名称：

  Efficient synthesis of a molecular knot by copper(I)-induced formation of the precursor followed by ruthenium(II)-catalysed ring closing metathesis

  摘要：

  通过钌（II）催化的闭环甲烷化反应（RCM），以两个铜（I）中心为模板构建的、带有四个末端烯烃的双链螺旋被转化为三叶虫结，收率为 74%；环烯烃可以通过催化氢化定量还原，从而得到铜（I）络合的 82 元结环。

  DOI：

  10.1039/a704970f

文献信息

• Efficient synthesis of a molecular knot by copper(I)-induced formation of the precursor followed by ruthenium(II)-catalysed ring closing metathesis
  作者：Christiane Dietrich-Buchecker、Gwénaël Rapenne

  DOI：10.1039/a704970f

  日期：——

  A double-stranded helix constructed around two copper(I) centres used as templates and bearing four terminal alkenes, is converted into a trefoil knot in 74% yield by ruthenium(II)-catalysed ring closing methathesis (RCM); the cyclic alkenes can be quantitatively reduced by catalytic hydrogenation to afford the copper(I)-complexed 82-membered knotted ring.

  通过钌（II）催化的闭环甲烷化反应（RCM），以两个铜（I）中心为模板构建的、带有四个末端烯烃的双链螺旋被转化为三叶虫结，收率为 74%；环烯烃可以通过催化氢化定量还原，从而得到铜（I）络合的 82 元结环。
• Copper(I)- or Iron(II)-Templated Synthesis of Molecular Knots Containing Two Tetrahedral or Octahedral Coordination Sites
  作者：Gwénaël Rapenne、Christiane Dietrich-Buchecker、Jean-Pierre Sauvage

  DOI：10.1021/ja982239+

  日期：1999.2.1

  Molecular trefoil knots have been prepared from metal-assembled precursors using the ring closing metathesis (RCM) cyclization methodology. The templating metal is either copper(I) or iron(II) and the coordinating fragments 1,10-phenanthroline or 2,2':6',2 "-terpyridine, respectively. The RCM approach, newly applied to the field of catenanes and knots, represents a spectacular synthetic improvement in terms of yield and experimental conditions (no high dilution required). The dicopper(I) trefoil knot has been synthesized in a 74% yield. A similar approach also led to the first knot constructed around two iron(II) bis(terpyridine) moieties, demonstrating that iron(II) can also be used as a highly efficient template. Moreover, for both Cu(I) and Fe(II) knots, it has been possible to quantitatively reduce the cyclic olefins formed during the macrocyclization by catalytic (Pd/C) hydrogenation. An X-ray structure of the double helix of iron(II) bis(1,2-bis(5-(5 "-methyl-2,2':6',2 "-terpyridinyl))ethane) is given which shows that the double-stranded helical precursor is well predisposed for the formation of a molecular knot.