3,17β-bisbenzyloxy-11α-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-estra-1,3,5(10)-trien-11β-ol | 1095001-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3,17β-bisbenzyloxy-11α-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-estra-1,3,5(10)-trien-11β-ol
• CAS: 1095001-13-0
• 化学式: C₄₂H₃₉F₁₇O₃
• 分子量: 914.743
• InChiKey: DLMQBAIKADFLAU-ZGSWEVDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.84
• 重原子数：
  62.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,17β-bisbenzyloxy-11α-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-estra-1,3,5(10)-trien-11β-ol 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以51%的产率得到3,17β-bisbenzyloxy-11β-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-estra-1,3,5(10)-triene
  参考文献：
  名称：

  Fluorous tolerance of the estrogen receptor alpha as probed by 11-polyfluoroalkylestradiol derivatives

  摘要：

  The concern of this work was to try to delineate factors, inherent to fluorination, susceptible to influence estradiol binding to the estrogen receptor alpha (ER alpha). For this purpose, fluorinated chains were linked at 11 beta position of the steroid (i.e., C6F13, CH2CH2C4F9, CH2CH2C8F17)-Relative binding affinity (RBA) for ER alpha of these compounds and of other related fluorinated derivatives was compared to those of non-fluorinated analogs. Despite being relatively well accepted by the receptor, investigated compounds exhibited lower RBA values at 0 degrees C than their non-fluorinated counterparts. Nevertheless, heavily fluorinated chains were tolerated in so far as they are not too long (C-4) and insulated from the steroidal core by a two methylene spacer unit. Increase of the temperature of our binding assay (25 degrees C) failed to change the RBA values of two selected polyfluorohexyl derivatives while it drastically enhanced the value of the corresponding non-fluorinated analogs. Rigidity of the chain induced by fluorination as well as the oleophilic (fluorophobic) nature of the estradiol binding cavity of ER alpha is proposed to explain these properties. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.11.002
• 作为产物：
  描述：

  、 3,17β-dibenzyloxyestra-1,3,5(10)-trien-11-one 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 以36%的产率得到3,17β-bisbenzyloxy-11α-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-estra-1,3,5(10)-trien-11β-ol
  参考文献：
  名称：

  Fluorous tolerance of the estrogen receptor alpha as probed by 11-polyfluoroalkylestradiol derivatives

  摘要：

  The concern of this work was to try to delineate factors, inherent to fluorination, susceptible to influence estradiol binding to the estrogen receptor alpha (ER alpha). For this purpose, fluorinated chains were linked at 11 beta position of the steroid (i.e., C6F13, CH2CH2C4F9, CH2CH2C8F17)-Relative binding affinity (RBA) for ER alpha of these compounds and of other related fluorinated derivatives was compared to those of non-fluorinated analogs. Despite being relatively well accepted by the receptor, investigated compounds exhibited lower RBA values at 0 degrees C than their non-fluorinated counterparts. Nevertheless, heavily fluorinated chains were tolerated in so far as they are not too long (C-4) and insulated from the steroidal core by a two methylene spacer unit. Increase of the temperature of our binding assay (25 degrees C) failed to change the RBA values of two selected polyfluorohexyl derivatives while it drastically enhanced the value of the corresponding non-fluorinated analogs. Rigidity of the chain induced by fluorination as well as the oleophilic (fluorophobic) nature of the estradiol binding cavity of ER alpha is proposed to explain these properties. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.11.002