3β-[(tert-butyldimethylsilyl)oxy]-17α-ethynyl-5α-androstan-17β-ol | 1404499-79-1

• 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: 3β-[(tert-butyldimethylsilyl)oxy]-17α-ethynyl-5α-androstan-17β-ol
• 英文别名: (3S,5S,8R,9S,10S,13S,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-ethynyl-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-ol
• CAS: 1404499-79-1
• 化学式: C₂₇H₄₆O₂Si
• 分子量: 430.747
• InChiKey: FHHIQZBREMRTCU-ZOLRUJEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.02h， 生成 3β-[(tert-butyldimethylsilyl)oxy]-17α-ethynyl-5α-androstan-17β-ol
  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

• Formylated polyamines as peptidomimetics
  作者：Sacha Javor、Aaron Janowsky、Robert Johnson、Katherine Wolfrum、Mitra Tadayoni-Rebek、Julius Rebek

  DOI：10.1016/j.bmcl.2012.09.008

  日期：2012.11

  A new construct for imitating a natural peptide ligand using a modified retro-inverso sequence is described. It is demonstrated through the synthesis of a peptidomimetic derived from the endogenous sequence of leucine enkephalin. The product was active at 400 nM and selective for mu-opioid receptors. (C) 2012 Elsevier Ltd. All rights reserved.