2-(triptycene-9-yl)-1,3-dioxolane | 1469-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(triptycene-9-yl)-1,3-dioxolane
• 英文别名: Triptycen-9-carboxaldehyd-ethylenacetal；2-(1-Pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaenyl)-1,3-dioxolane
• CAS: 1469-55-2
• 化学式: C₂₃H₁₈O₂
• 分子量: 326.395
• InChiKey: ORLSOXCBYURDKL-UHFFFAOYSA-N

物化性质

• 熔点：
  287.1-287.4 °C
• 沸点：
  448.2±40.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(triptycene-9-yl)-1,3-dioxolane 在 盐酸 、 正丁基锂 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 37.75h， 生成 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：

  环己-1,3-二烯-5-炔 、 2-(anthracen-9-yl)-1,3-dioxolane 以64%的产率得到2-(triptycene-9-yl)-1,3-dioxolane
  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

• Triptycene Derivatives as Medicinal Agents
  作者：Edmund C. Kornfeld、Pam Barney、John Blankley、William Faul

  DOI：10.1021/jm00327a013

  日期：1965.5
• 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.