1,4-bis[3α-(but-3-enoyloxy)-17β-hydroxy-5α-androstan-17α-yl-ethynyl]-2,3-difluorobenzene | 1404499-83-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1,4-bis[3α-(but-3-enoyloxy)-17β-hydroxy-5α-androstan-17α-yl-ethynyl]-2,3-difluorobenzene
• 英文别名: 1,4-bis[3α-(but-3′-enoyloxy)-17β-hydroxy-5α-androstan-17α-ylethynyl]benzene
• CAS: 1404499-83-7
• 化学式: C₅₆H₇₄O₆
• 分子量: 843.2
• InChiKey: AZCAPLSJCCOCIH-BWKBFLLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.91
• 重原子数：
  62.0
• 可旋转键数：
  6.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,4-bis[3α-(but-3-enoyloxy)-17β-hydroxy-5α-androstan-17α-yl-ethynyl]-2,3-difluorobenzene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 、
  参考文献：
  名称：

  Macrocyclic Molecular Rotors with Bridged Steroidal Frameworks

  摘要：

  In this work, we describe the synthesis and solid-state dynamics of isomeric molecular rotors 7E and 7Z, consisting of two androstane steroidal frameworks linked by the D rings by triple bonds at their C17 positions to a 1,4-phenylene rotator. They are also linked by the A rings by an alkenyl diester bridge to restrict the conformational flexibility of the molecules and reduce the number of potential crystalline arrays. The analysis of the resulting molecular structures and packing motifs offered insights of the internal dynamics that were later elucidated by means of line shape analyses of the spectral features obtained through variable-temperature solid-state C-13 NMR; such analysis revealed rotations in the solid state occurring at kilohertz frequency at room temperature.

  DOI：

  10.1021/jo3020402
• 作为产物：
  描述：

  3β-[(tert-butyldimethylsilyl)oxy]-17α-ethynyl-5α-androstan-17β-ol 在 四(三苯基膦)钯 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 41.17h， 生成 1,4-bis[3α-(but-3-enoyloxy)-17β-hydroxy-5α-androstan-17α-yl-ethynyl]-2,3-difluorobenzene
  参考文献：
  名称：

  Macrocyclic Molecular Rotors with Bridged Steroidal Frameworks

  摘要：

  In this work, we describe the synthesis and solid-state dynamics of isomeric molecular rotors 7E and 7Z, consisting of two androstane steroidal frameworks linked by the D rings by triple bonds at their C17 positions to a 1,4-phenylene rotator. They are also linked by the A rings by an alkenyl diester bridge to restrict the conformational flexibility of the molecules and reduce the number of potential crystalline arrays. The analysis of the resulting molecular structures and packing motifs offered insights of the internal dynamics that were later elucidated by means of line shape analyses of the spectral features obtained through variable-temperature solid-state C-13 NMR; such analysis revealed rotations in the solid state occurring at kilohertz frequency at room temperature.

  DOI：

  10.1021/jo3020402

文献信息

• Solid State Characterization of Bridged Steroidal Molecular Rotors: Effect of the Rotator Fluorination on Their Crystallization
  作者：Dorota Czajkowska-Szczykowska、Andrés Aguilar-Granda、Jadwiga Maj、Agnieszka Z. Wilczewska、Stanisław Witkowski、Rosa Santillan、Miguel A. Garcia-Garibay、Jacek W. Morzycki、Braulio Rodríguez-Molina

  DOI：10.1021/acs.cgd.5b01705

  日期：2016.3.2

  crystallization of two macrocyclic steroidal compounds labeled (Z)-1F2 and (E)-1F2, envisioned to work as molecular rotors with 1,4-diethynyl-2,3-difluorophenylene rotators. The introduction of the fluorine atoms rendered different crystal arrays that were fully characterized by X-ray diffraction, solid state 13C NMR, and calorimetric experiments. In both isomers, the central molecular fragments point the o-fluorine

  我们描述了标记为（Z）-1F 2和（E）-1F 2的两个大环甾体化合物的合成和结晶，设想它们可作为具有1,4-二乙炔基-2,3-二氟亚苯基转子的分子转子。氟原子的引入产生了不同的晶体阵列，这些晶体阵列已通过X射线衍射，固态13 C NMR和量热实验进行了全面表征。在这两种异构体中，中心分子片段都将邻氟原子指向其腔体，突出了固态的首选取向。通过分析晶体阵列，可以看出，氟化Z异构体与其非氟化类似物是同构的，E异构体在未预期的晶体阵列中显示出显着的结构变异，每个不对称单元有两个分子（Z '= 2）。