3,3',3''-(3-(4-(3,3,3-tris(3-((10-bromodecyl)oxy)phenyl)prop-1-yn-1-yl)phenyl)prop-2-yne-1,1,1-triyl)triphenol | 950773-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3,3',3''-(3-(4-(3,3,3-tris(3-((10-bromodecyl)oxy)phenyl)prop-1-yn-1-yl)phenyl)prop-2-yne-1,1,1-triyl)triphenol
• CAS: 950773-63-4
• 化学式: C₇₈H₉₁Br₃O₆
• 分子量: 1364.29
• InChiKey: OJRTXPOSBFXEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.26
• 重原子数：
  87.0
• 可旋转键数：
  39.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,3',3''-(3-(4-(3,3,3-tris(3-((10-bromodecyl)oxy)phenyl)prop-1-yn-1-yl)phenyl)prop-2-yne-1,1,1-triyl)triphenol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以27%的产率得到7,18,30,41,52,63-Hexaoxadecacyclo[22.22.22.81,24.12,6.119,23.125,29.142,46.147,51.164,68.275,78]tetraoctaconta-2(82),3,5,19,21,23(81),25(72),26,28,42,44,46(71),47(70),48,50,64,66,68,75(84),76,78(83)-henicosaen-73,79-diyne
  参考文献：
  名称：

  Synthesis of a Triply-Bridged Molecular Gyroscope by a Directed Meridional Cyclization Strategy

  摘要：

  A crystalline triply bridged molecular gyroscope has been prepared and analyzed by single-crystal X-ray diffraction. A convergent synthetic strategy was developed to control the direction of the three bridges, from the preferred two zonal and one meridional arrangement of a one-step cylclization process to the directed three meridional bridges achieved by a north-south desymmetrization.

  DOI：

  10.1021/ol071379y
• 作为产物：
  描述：

  1,10-二溴癸烷 在 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.25h， 生成 3,3',3''-(3-(4-(3,3,3-tris(3-((10-bromodecyl)oxy)phenyl)prop-1-yn-1-yl)phenyl)prop-2-yne-1,1,1-triyl)triphenol
  参考文献：
  名称：

  Synthesis of a Triply-Bridged Molecular Gyroscope by a Directed Meridional Cyclization Strategy

  摘要：

  A crystalline triply bridged molecular gyroscope has been prepared and analyzed by single-crystal X-ray diffraction. A convergent synthetic strategy was developed to control the direction of the three bridges, from the preferred two zonal and one meridional arrangement of a one-step cylclization process to the directed three meridional bridges achieved by a north-south desymmetrization.

  DOI：

  10.1021/ol071379y

文献信息

• Synthesis of Bridged Molecular Gyroscopes with Closed Topologies: Triple One-Pot Macrocyclization
  作者：Patrick Commins、Jose E. Nuñez、Miguel A. Garcia-Garibay

  DOI：10.1021/jo201513y

  日期：2011.10.21

  We describe the synthesis and characterization of six bridged molecular gyroscopes with m-alkoxy-substituted trityl stators and dialkynylphenylene rotators. All of the bridged molecular gyroscopes were synthesized convergently to form the phenolic stator-rotator framework, while the alkyl and benzophenone bridges were installed in one step by relatively efficient one-pot reactions to form macrocyclic diether or diester linkages. The isolated yield per bond-forming reaction varied from ca. 42% to 80%, with one exception where macrocyclization failed to produce the desired product. The molecular structure and crystal packing of each of the bridged molecular gyroscopes were determined via single crystal X-ray diffraction. Like most molecular gyroscopes with open topologies previously studied, the singly bridged structures pack by interdigitating one trityl stator in one molecule next to the rotator of an adjacent molecule in the lattice. In contrast, the triply bridged molecular gyroscopes were found to pack in lamellar sheets that prevent the rotator-stator interdigitation of adjacent molecules. However, solvent molecules and conformationally flexible bridges tend to fill in the packing volume by collapsing next to the rotator or by extending one of their bridges into the cavity of a neighboring molecule.