9-(2,2-dibromoethen-1-yl)triptycene | 207565-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(2,2-dibromoethen-1-yl)triptycene
• 英文别名: 9-(2,2-dibromoethenyl)triptycene；1-(2,2-Dibromoethenyl)pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
• CAS: 207565-35-3
• 化学式: C₂₂H₁₄Br₂
• 分子量: 438.161
• InChiKey: IRMTVKQIQFULGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(2,2-dibromoethen-1-yl)triptycene 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以99%的产率得到9-ethynyltriptycene
  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-(triptycene-9-yl)-1,3-dioxolane 在 盐酸 、 三苯基膦 、 锌 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 9-(2,2-dibromoethen-1-yl)triptycene
  参考文献：
  名称：

  New Molecular Devices:  In Search of a Molecular Ratchet

  摘要：

  The triptycene-substituted [3]- and [4]helicenes 1 and 2 were examined as possible molecular versions of mechanical ratchets, where the triptycene serves as the ratchet wheel and the helicenes as pawl and spring. The syntheses of 1 and 2b are described. H-1 NMR was employed to examine rotation around the triptycene/helicene single bond; at 20 degrees C rotation is frozen for both 1 and 2b, but the NMR of 1 revealed a plane of symmetry, indicating that 1 cannot function as a unidirectional ratchet. In contrast, NMR revealed that, like a ratchet, triptycyl[4]helicene 2b lacks the symmetry of 1 and has a barrier to rotation of 24.5 kcal/mol, but spin polarization transfer NMR experiments indicated the triptycene in 2b nonetheless rotates equally in both directions. That outcome is rationalized from the standpoint of thermodynamics.

  DOI：

  10.1021/jo9723218

文献信息

• New Molecular Devices:  In Search of a Molecular Ratchet
  作者：T. Ross Kelly、José Pérez Sestelo、Imanol Tellitu

  DOI：10.1021/jo9723218

  日期：1998.5.1

  The triptycene-substituted [3]- and [4]helicenes 1 and 2 were examined as possible molecular versions of mechanical ratchets, where the triptycene serves as the ratchet wheel and the helicenes as pawl and spring. The syntheses of 1 and 2b are described. H-1 NMR was employed to examine rotation around the triptycene/helicene single bond; at 20 degrees C rotation is frozen for both 1 and 2b, but the NMR of 1 revealed a plane of symmetry, indicating that 1 cannot function as a unidirectional ratchet. In contrast, NMR revealed that, like a ratchet, triptycyl[4]helicene 2b lacks the symmetry of 1 and has a barrier to rotation of 24.5 kcal/mol, but spin polarization transfer NMR experiments indicated the triptycene in 2b nonetheless rotates equally in both directions. That outcome is rationalized from the standpoint of thermodynamics.
• Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators
  作者：Derik K. Frantz、Anthony Linden、Kim K. Baldridge、Jay S. Siegel

  DOI：10.1021/ja2063346

  日期：2012.1.25

  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.