9-(2,2-dibromoethen-1-yl)-4-(trifluoromethyl)triptycene | 1353014-60-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 9-(2,2-dibromoethen-1-yl)-4-(trifluoromethyl)triptycene
• CAS: 1353014-60-4
• 化学式: C₂₃H₁₃Br₂F₃
• 分子量: 506.159
• InChiKey: IMMGSOUPGWJAJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.48
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  9-(2,2-dibromoethen-1-yl)-4-(trifluoromethyl)triptycene 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 以94%的产率得到9-ethynyl-4-(trifluoromethyl)triptycene
  参考文献：
  名称：

  Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators

  摘要：

  Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

  DOI：

  10.1021/ja2063346
• 作为产物：
  描述：

  2-[4-(trifluoromethyl)triptycene-9-yl]-1,3-dioxolane 在 盐酸 、 溶剂黄146 、 三苯基膦 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 32.25h， 生成 9-(2,2-dibromoethen-1-yl)-4-(trifluoromethyl)triptycene
  参考文献：
  名称：

  Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators

  摘要：

  Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

  DOI：

  10.1021/ja2063346

文献信息

• Molecular Spur Gears with Triptycene Rotators and a Norbornane-Based Stator
  作者：Xing Jiang、Song Yang、Marcus J. Jellen、K. N. Houk、Miguel Garcia-Garibay

  DOI：10.1021/acs.orglett.0c01029

  日期：2020.6.5

  We report efforts to prepare a molecular spur gear utilizing a convenient synthesis of a norbornane stator that positions two interdigitated diyne-linked triptycenes in parallel alignment. While gearing was not observed by 19F NMR for a −CF3-labeled analog at temperatures as low as 213 K, we used molecular dynamics simulation and 2D metadynamics calculations to understand the gearing/slippage energetic

  我们报告了努力准备利用分子合成降冰片烷定子的便利合成的分子正齿轮，该定子在平行排列中定位两个相互交叉的二炔连接的三联烯。虽然在低至213 K的温度下未通过19 F NMR观察到-CF 3标记的类似物的齿轮，但我们使用分子动力学模拟和2D元动力学计算来了解各种分子正齿轮的齿轮/滑移能量曲线，以指导未来这些系统的设计。