3,3-bis[3-((tert-butyl)diphenylsilanyloxy)phenyl]-3-phenylpropyne | 1392136-21-8

• 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-bis[3-((tert-butyl)diphenylsilanyloxy)phenyl]-3-phenylpropyne
• 英文别名: Tert-butyl-[3-[1-[3-[tert-butyl(diphenyl)silyl]oxyphenyl]-1-phenylprop-2-ynyl]phenoxy]-diphenylsilane；tert-butyl-[3-[1-[3-[tert-butyl(diphenyl)silyl]oxyphenyl]-1-phenylprop-2-ynyl]phenoxy]-diphenylsilane
• CAS: 1392136-21-8
• 化学式: C₅₃H₅₂O₂Si₂
• 分子量: 777.166
• InChiKey: RMMDUZGYAGZHDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.53
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1,4-二碘苯 、 3,3-bis[3-((tert-butyl)diphenylsilanyloxy)phenyl]-3-phenylpropyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以73%的产率得到1,4-bis(3,3-bis-[3-((tert-butyl)diphenylsilanyloxy)phenyl]-3-phenylpropynyl)benzene
  参考文献：
  名称：

  Synthesis and Evaluation of Molecular Rotors with Large and Bulky tert-Butyldiphenylsilyloxy-Substituted Trityl Stators

  摘要：

  The search for voluminous stators that may accommodate large rotator units and speed rotational dynamics in the solid state led us to investigate a simple and efficient method for the synthesis of molecular rotors with tert-butyldiphenylsilyl-protected (TBDPS) triphenylmethyl stators. Additionally, solid state characterization of these systems with two-, four-, and six-TBDPS groups provided us with a description of their crystallinity and thermal stability. Among them, molecular rotor 7c with the largest and most symmetric stator resulting from six peripheral silyl groups showed the best tendency to crystallize, and the study of its isotopologue 7c-d(4) by solid state H-2 NMR revealed a 2-fold motion of the 1,4-diethynylphenylene-d(4) rotator in the kHz regime.

  DOI：

  10.1021/jo301078a
• 作为产物：
  描述：

  (3-溴苯氧基)(叔丁基)二苯基硅烷 、 苯甲酸甲酯 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 55.5h， 生成 3,3-bis[3-((tert-butyl)diphenylsilanyloxy)phenyl]-3-phenylpropyne
  参考文献：
  名称：

  Synthesis and Evaluation of Molecular Rotors with Large and Bulky tert-Butyldiphenylsilyloxy-Substituted Trityl Stators

  摘要：

  The search for voluminous stators that may accommodate large rotator units and speed rotational dynamics in the solid state led us to investigate a simple and efficient method for the synthesis of molecular rotors with tert-butyldiphenylsilyl-protected (TBDPS) triphenylmethyl stators. Additionally, solid state characterization of these systems with two-, four-, and six-TBDPS groups provided us with a description of their crystallinity and thermal stability. Among them, molecular rotor 7c with the largest and most symmetric stator resulting from six peripheral silyl groups showed the best tendency to crystallize, and the study of its isotopologue 7c-d(4) by solid state H-2 NMR revealed a 2-fold motion of the 1,4-diethynylphenylene-d(4) rotator in the kHz regime.

  DOI：

  10.1021/jo301078a

文献信息

• Synthesis and Evaluation of Molecular Rotors with Large and Bulky <i>tert</i>-Butyldiphenylsilyloxy-Substituted Trityl Stators
  作者：Rafael Arcos-Ramos、Braulio Rodríguez-Molina、Margarita Romero、J. Manuel Méndez-Stivalet、María Eugenia Ochoa、Pedro I. Ramírez-Montes、Rosa Santillan、Miguel A. Garcia-Garibay、Norberto Farfán

  DOI：10.1021/jo301078a

  日期：2012.8.17

  The search for voluminous stators that may accommodate large rotator units and speed rotational dynamics in the solid state led us to investigate a simple and efficient method for the synthesis of molecular rotors with tert-butyldiphenylsilyl-protected (TBDPS) triphenylmethyl stators. Additionally, solid state characterization of these systems with two-, four-, and six-TBDPS groups provided us with a description of their crystallinity and thermal stability. Among them, molecular rotor 7c with the largest and most symmetric stator resulting from six peripheral silyl groups showed the best tendency to crystallize, and the study of its isotopologue 7c-d(4) by solid state H-2 NMR revealed a 2-fold motion of the 1,4-diethynylphenylene-d(4) rotator in the kHz regime.