3-(3-methoxyphenyl)-3,3-diphenylpropyne | 1354901-61-3

• 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-methoxyphenyl)-3,3-diphenylpropyne
• 英文别名: 1-(1,1-Diphenylprop-2-ynyl)-3-methoxybenzene
• CAS: 1354901-61-3
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: YFUHLEUARMIQLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3-methoxyphenyl)-3,3-diphenylpropyne 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 三溴化硼 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 4,4,27,27-Tetraphenyl-10,21-dioxatetracyclo[28.2.2.15,9.122,26]hexatriaconta-1(33),5(36),6,8,22,24,26(35),30(34),31-nonaen-2,28-diyne-11,20-dione
  参考文献：
  名称：

  Synthesis of Bridged Molecular Gyroscopes with Closed Topologies: Triple One-Pot Macrocyclization

  摘要：

  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.

  DOI：

  10.1021/jo201513y
• 作为产物：
  描述：

  (3-甲氧基苯基)二苯基甲醇 在 乙酰氯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.0h， 生成 3-(3-methoxyphenyl)-3,3-diphenylpropyne
  参考文献：
  名称：

  Synthesis of Bridged Molecular Gyroscopes with Closed Topologies: Triple One-Pot Macrocyclization

  摘要：

  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.

  DOI：

  10.1021/jo201513y

文献信息

• Linear Relationship between ¹³ C NMR Chemical Shifts and the Bending of sp‐Carbon Chains
  作者：Mathis Kreuzahler、Abdulselam Adam、Gebhard Haberhauer

  DOI：10.1002/chem.201902617

  日期：2019.10

  of the nonlinearity in solution. Herein, we show that the 13 C NMR spectroscopy represents an appropriate tool for this as we found an almost perfect linear relationship between the bending of the alkyne chain and the change of the chemical shift of the outer acetylenic carbon atoms. By using molecular bows in which the alkyne chain can be bent by switching the azobenzene unit, this correlation can be

  Polyynes在能量影响和Polyyne链的弯曲之间显示出严格的线性关系。弯曲炔链所需的能量随着乙炔单元数目的增加而降低。违反红外和拉曼光谱之间的互斥原理，可以在解决方案中实现多炔的线性度偏差。但是，仍然不可能测量溶液中的非线性程度。本文中，我们显示13 C NMR光谱为此提供了一种合适的工具，因为我们发现炔烃链的弯曲与外部炔碳原子化学位移的变化之间存在几乎完美的线性关系。通过使用其中可以通过切换偶氮苯单元来弯曲炔烃链的分子弓，可以通过实验证明这种相关性。将来，这种相关性应该能够确定弯曲的程度和聚炔的应变能。因此，聚炔可以用作测量进一步的分子力的探针。
• Synthesis, Rotational Dynamics, and Photophysical Characterization of a Crystalline Linearly Conjugated Phenyleneethynylene Molecular Dirotor
  作者：Melissa Hughs、Miguel Jimenez、Saeed Khan、Miguel A. Garcia-Garibay

  DOI：10.1021/jo4004053

  日期：2013.6.7

  which the two flanking ethynylphenylene rotators can explore various torsion angles; this allows the BEPEB fluorophore dynamics to persist in the solid state. X-ray diffraction studies have shown that molecular dirotor 1 is packed so that all the BEPEB fluorophores adopt a parallel alignment, this is ideal for the development of functional materials. Variable temperature, quadrupolar echo 2H NMR studies

  我们报告6,13-​​双（（4-（3-（3-（3-甲氧基苯基）-3,3-二苯基丙-1-yn-1-yl）苯基）的合成，晶体结构，固态动力学和光物理性质乙炔基）-5,7,12,14-四氢-5,14：7,12-双（[1,2，benzeno）并五苯（1），具有1,4-双（（4-乙炔基苯基）乙炔基苯（BEPEB）发色团。戊二烯结合到分子转子中提供了一个中心定子和一个固定的亚苯基环，两个侧键的乙炔基亚苯基转子可相对于它们探索不同的扭转角。这样可以使BEPEB荧光团动力学保持固态。X射线衍射研究表明分子转子1包装好使所有BEPEB荧光团都采用平行排列，这对于功能材料的开发是理想的。可变温度，四极回波21 H NMR研究表明，亚苯基旋转翻转具有9.0kcal / mol的活化能和约2.6MHz的室温翻转频率。最后，通过在溶液，玻璃和晶体中的测量，我们获得了证据，亚苯基亚乙炔发色团的荧光激发和发射光谱取决于
• Photochromic Molecular Gyroscope with Solid State Rotational States Determined by an Azobenzene Bridge
  作者：Patrick Commins、Miguel A. Garcia-Garibay

  DOI：10.1021/jo402516n

  日期：2014.2.21

  photochemical isomerization, and rotational dynamics of a crystalline molecular gyroscope containing an azobenzene bridge (trans-2) that spans from one end of the stator to other, with the intention of exploring its function as a molecular brake. While single crystal X-ray diffraction analysis of a photochemically inactive dichloromethane solvate was used to confirm the molecular and packing structures of

  我们描述了包含偶氮苯桥（trans - 2）的晶体分子陀螺仪的合成，表征，光化学异构化和旋转动力学，该偶氮苯桥跨越从定子的一端到另一端，以探索其作为分子制动器的功能。虽然使用了光化学非活性二氯甲烷溶剂化物的单晶X射线衍射分析，以确认的分子和包装结构的反式- 2，纳米晶体假多被证明是光活性的，并且它是由粉末X射线衍射（PXRD）分析，扫描电子显微镜和可变温度固态2光异构化前后的1 H NMR。结果表明，与在溶液中观察到的相应值是74％的溶液相比，用λ= 340 nm照射的纳米晶体悬浮液具有34％的顺式异构体达到了光平稳状态。对苯并d 4同位素分子的固态2 H NMR光谱进行线形分析（随温度变化），表明反式2异构体晶体的旋转，平均活化能为4.6±0.6 kcal / mol，前指数因子exp（29.4±1.7）比包含cis- 2的样品快十倍 异构体，其平均活化能较高，为5.1±0.6 kcal
• 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.