2-(anthracen-9-yl)-1,3-dioxolane | 4764-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(anthracen-9-yl)-1,3-dioxolane
• 英文别名: 2-anthracen-9-yl[1,3]dioxolane；9-[1,3]dioxolan-2-yl-anthracene；9-[1,3]Dioxolan-2-yl-anthracen；1,3-Dioxolane, 2-(9-anthracenyl)-；2-anthracen-9-yl-1,3-dioxolane
• CAS: 4764-28-7
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: RDPZFVZDKKOOAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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-(anthracen-9-yl)-1,3-dioxolane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 39.0h， 生成 1,1'-bis(tert-butoxycarbonyl)-4,4'-bis(4-methyltriptycen-9-ylethynyl)-6,6'-di-tert-butyl-2,2'-bibenzimidazole
  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：

  9-蒽甲醛 在 对甲苯磺酸 、 乙二醇 作用下， 生成 2-(anthracen-9-yl)-1,3-dioxolane
  参考文献：
  名称：

  Rio; Sillion, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1957, vol. 244, p. 623,625

  摘要：

  DOI：

文献信息

• Acid-Catalyzed Transacetalization from Glycol to Pinacol Acetals
  作者：Yvonne Seeleib、Gregor Nemecek、Dominik Pfaff、Bastian D. Süveges、Joachim Podlech

  DOI：10.1080/00397911.2014.912330

  日期：2014.10.18

  transacetalization of glycol acetals, frequently used as protecting groups of the aldehyde function, into the more stable pinacol acetals is given. A clean transformation of aromatic and aliphatic substrates is possible with trifluoroacetic acid within 30 min at 0 °C. Glycol acetals derived from ketones (ketals) cannot be converted with this protocol. Deprotection of the pinacol acetals is possible with

  摘要 给出了通常用作醛官能团保护基团的乙二醇缩醛的一锅转缩醛转化为更稳定的频哪醇缩醛。在 0 °C 下，使用三氟乙酸可在 30 分钟内实现芳香族和脂肪族底物的彻底转化。从酮（缩酮）衍生的乙二醇缩醛不能用此协议转换。频哪醇缩醛的脱保护可以在水存在下用三氟甲磺酸进行。图形概要
• Rotational Isomerism and Atropisomerism in Acetal Derivatives of 1,2,3,4-Tetrafluorotriptycene-9-carbaldehyde
  作者：Gaku Yamamoto

  DOI：10.1246/bcsj.65.1967

  日期：1992.7

  In the ethylene acetal (2) of 1,2,3,4-tetrafluorotriptycene-9-carbaldehyde, equal amounts of the ap and ±sc rotamers exist in CDCl3 at equilibrium, while the equilibrium is strongly shifted to ±sc in the corresponding dimethyl and trimethylene acetals. Molecular mechanics calculations reveal the origin of this anomaly to reside in the conformation of the acetal moiety. Dynamic NMR studies show that

  在 1,2,3,4-四氟三苯乙烯-9-甲醛的乙缩醛 (2) 中，CDCl3 中存在等量的 ap 和 ±sc 旋转异构体，而平衡在相应的二甲基苯胺中强烈移动至 ±sc和三亚甲基缩醛。分子力学计算揭示了这种异常的起源在于缩醛部分的构象。动态 NMR 研究表明 ap → ±sc 势垒太低，无法在这些化合物中实现阻转异构（ΔG≠ ca. 21–22 kcal mol-1 (1 calth = 4.184 J)）。然而，利用不寻常的平衡行为，通过从平衡的旋转异构体混合物的溶液中选择性结晶一个旋转异构体，将 2 的两个旋转异构体分离为晶体。
• Molecular Spur Gears Based on a Switchable Quinquepyridine Foldamer Acting as a Stator
  作者：Fu Huang、Guangxia Wang、Lishuang Ma、Ying Wang、Xuebo Chen、Yanke Che、Hua Jiang

  DOI：10.1021/acs.joc.7b01864

  日期：2017.12.1

  quinquepyridine (QPY) foldamer at the second and fourth pyridine rings, respectively, to form molecular spur gears. The studies revealed that a QPY foldamer as a stator can reversibly control the intermeshed and demeshed states of molecular spur gears due to the linear-to-helical conformational switching triggered by complexation/decomplexation.

  两个三茂铁旋转器已分别在第二和第四吡啶环上共价连接到喹吡啶（QPY）折叠架的主链上，以形成分子正齿轮。研究表明，QPY折叠器作为定子可以逆转地控制分子正齿轮的相互啮合和脱离啮合状态，这是由于络合/分解作用引起的线性-螺旋构象转换所致。
• Strong Participation of the 1-Methyl Group in Diazotization Reaction of 9-Aminomethyl-1,4-dimethyltriptycene
  作者：Gaku Yamamoto、Michinori Oki

  DOI：10.1246/cl.1987.1163

  日期：1987.6.5

  The title reaction in acetic acid gave 5-methyl-1,2,6,10b-tetrahydro-6,10b-o-benzenoaceanthrylene and 1-acetoxymethyl-4,9-dimethyltriptycene as major products and only small amounts of skeletally rearranged homotriptycene derivatives to indicate strong participation of the peri-methyl group in the reaction.

  乙酸中的标题反应产生了5-甲基-1,2,6,10b-四氢-6,10b-邻苯乙酰蒽和1-乙酰氧甲基-4,9-二甲基三联苯，以及少量骨架重排的同三联苯衍生物，表明甲基周围基团强烈参与了反应。
• Mulzer, Johann; Trauner, Dirk; Bats, Jan W., Angewandte Chemie, 1996, vol. 108, # 17, p. 2093 - 2095
  作者：Mulzer, Johann、Trauner, Dirk、Bats, Jan W.

  DOI：——

  日期：——