4-(3',3',3'-triphenylpropyn-1-yl)-1-iodobenzene | 444578-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3',3',3'-triphenylpropyn-1-yl)-1-iodobenzene
• 英文别名: 1-iodo-4-(3,3,3-triphenylpropynyl)benzene；1-iodo-4-(2-tritylethynyl)benzene；1-Iodo-4-(3,3,3-triphenyl-1-propyn-1-yl)benzene；1-iodo-4-(3,3,3-triphenylprop-1-ynyl)benzene
• CAS: 444578-41-0
• 化学式: C₂₇H₁₉I
• 分子量: 470.352
• InChiKey: XRQRPSUSKXIZCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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-ethynyltriptycene 、 4-(3',3',3'-triphenylpropyn-1-yl)-1-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以71%的产率得到1-[2-(9-triptycyl)ethynyl-4-(3,3,3-triphenylpropynyl)]benzene
  参考文献：
  名称：

  Improved Physical Properties and Rotational Dynamics in a Molecular Gyroscope with an Asymmetric Stator Structure

  摘要：

  A molecular gyroscope consisting of a 1,4-diethynylphenylene rotator linked to trityl and triptycyl groups ( 3) showed significantly improved physical properties and faster rotational dynamics than analogous symmetric bis(trityl) ( 1) or bis( triptycyl) ( 2) structures. An activation energy of 7.9 kcal/mol for 3 was determined by H-2 NMR. This is ca. 4-6 kcal/mol lower than that of compound 1. The different dynamics of the three compounds can be qualitatively understood in terms of their different packing coefficients.

  DOI：

  10.1021/ol060894d
• 作为产物：
  描述：

  1,4-二碘苯 、 tritylacetylene 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 以44%的产率得到4-(3',3',3'-triphenylpropyn-1-yl)-1-iodobenzene
  参考文献：
  名称：

  Improved Physical Properties and Rotational Dynamics in a Molecular Gyroscope with an Asymmetric Stator Structure

  摘要：

  A molecular gyroscope consisting of a 1,4-diethynylphenylene rotator linked to trityl and triptycyl groups ( 3) showed significantly improved physical properties and faster rotational dynamics than analogous symmetric bis(trityl) ( 1) or bis( triptycyl) ( 2) structures. An activation energy of 7.9 kcal/mol for 3 was determined by H-2 NMR. This is ca. 4-6 kcal/mol lower than that of compound 1. The different dynamics of the three compounds can be qualitatively understood in terms of their different packing coefficients.

  DOI：

  10.1021/ol060894d

文献信息

• Molecular “Compasses” and “Gyroscopes.” III. Dynamics of a Phenylene Rotor and Clathrated Benzene in a Slipping-Gear Crystal Lattice
  作者：Zaira Dominguez、Hung Dang、M. Jane Strouse、Miguel A. Garcia-Garibay

  DOI：10.1021/ja025753v

  日期：2002.7.1

  adjacent benzene molecules and phenylene groups suggested by the clathrate structure was investigated. However, it was found that 6-fold rotation of benzene molecules at 300 K occurs in the gigahertz regime (or higher) and 2-fold flipping of phenylene groups in the kilohertz range in a structure that can be described as a slipping-gear lattice. The rotational dynamics of the phenylene group in the solvent-free

  1,4-双 (3,3,3-三苯基丙炔基) 苯 3 的样品是通过 Pd(0) 催化偶联 3,3,3-三苯基丙炔 (1) 和 1,4-二碘苯制备的。化合物3的结构使得中心亚苯基可以起到陀螺轮的作用，而炔键和三苯甲基可以分别充当轴和屏蔽骨架。从苯和二氯甲烷中生长的晶体通过 X 射线衍射、变温 (13) C CPMAS 核磁共振、四极回波固态 (2) H 核磁共振和热分析进行了表征。苯分子和亚苯基的旋转动力学分别用 6 倍旋转和 2 倍翻转模型表征。研究了包合物结构所暗示的相邻苯分子和亚苯基之间的传动机制的可能性。然而，发现苯分子在 300 K 下旋转 6 倍发生在千兆赫兹范围内（或更高）和亚苯基在千赫兹范围内发生 2 倍翻转，这种结构可以描述为滑动齿轮晶格。无溶剂结构中亚苯基的旋转动力学与包合物中的非常相似，两者都是已知的固体中亚苯基旋转最快的。这里呈现的结果为具有相关分子运动的结晶固体的设计和
• Synthesis and solid-state dynamics of molecular dirotors
  作者：Stephanie L. Gould、Richard B. Rodriguez、Miguel A. Garcia-Garibay

  DOI：10.1016/j.tet.2008.05.143

  日期：2008.9

  dynamic NMR characterization of four new molecular dirotors, each containing two rotary 1,4-diethynyl phenylene units, a bridging 1,3-bis(diphenylmethyl) benzene stator, and two capping triphenylmethyl groups. These compounds are variations of the well-known wheel and axle structures. Ambient temperature quadrupolar echo 2H NMR spectra of phenylene-deuterated samples revealed line shapes consistent

  我们报告了四个新型分子双旋流器的设计，合成，热性质和动态NMR表征，每个分子含两个旋转的1,4-二乙炔基亚苯基单元，一个桥接的1,3-双（二苯基甲基）苯定子和两个封端的三苯基甲基基团。这些化合物是众所周知的车轮和车轴结构的变体。亚苯基氘化样品的环境温度四极回波2 H NMR光谱显示线形与交换速率> 10 8  s -1的动态过程一致，并且超过大多数亚苯基旋转器通常观察到的两个最小值。使用包含四个最小值（分别与0°，30°，180°和230°的角位移相关）的模型获得了合理的线形仿真。将样品冷却至260 K，显示出与包含两个或多个组分的样品一致的光谱。这些结果表明，新颖的轮轴结构确实会产生一定量的自由体积，从而允许旋转单元具有所需的移动性。