oxalic acid 11α-tridecafluorohexyl-3,17β-dibenzyloxyestra-1,3,5(10)-triene-11β-yl ester methyl ester | 869494-64-4

• 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: oxalic acid 11α-tridecafluorohexyl-3,17β-dibenzyloxyestra-1,3,5(10)-triene-11β-yl ester methyl ester
• 英文别名: 1-O-methyl 2-O-[(8S,9S,11S,13S,14S,17S)-13-methyl-3,17-bis(phenylmethoxy)-11-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-7,8,9,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-11-yl] oxalate
• CAS: 869494-64-4
• 化学式: C₄₁H₃₇F₁₃O₆
• 分子量: 872.72
• InChiKey: KJIFIYDQNPFGFC-OUYRWIGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  oxalic acid 11α-tridecafluorohexyl-3,17β-dibenzyloxyestra-1,3,5(10)-triene-11β-yl ester methyl ester 在 palladium on activated charcoal 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 11α-tridecafluorohexyl-3,17β-dihydroxyestra-1,3,5(10)-triene
  参考文献：
  名称：

  Synthesis of 11β-Perfluorohexylestradiol

  摘要：

  We report the synthesis of 11 beta-perfluorohexylestradiol le using a perfluoroorganometallic reagent for the introduction of the fluorous part. This compound is useful for biological studies and for imaging the ER alpha estradiol receptor distribution in the whole cell by secondary ion mass spectrometry (SIMS). The key step of this synthesis involves the radical reduction of an 11 beta-oxalate derivative. The stereochemical outcome of this reaction was studied for a range of C11 substituents, and we attempted to rationalize the apparent abnormal behavior of the phenyl group.

  DOI：

  10.1021/jo051424k
• 作为产物：
  描述：

  全氟己基碘烷 在 正丁基锂 、 甲基溴化镁 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 3.5h， 生成 oxalic acid 11α-tridecafluorohexyl-3,17β-dibenzyloxyestra-1,3,5(10)-triene-11β-yl ester methyl ester
  参考文献：
  名称：

  Synthesis of 11β-Perfluorohexylestradiol

  摘要：

  We report the synthesis of 11 beta-perfluorohexylestradiol le using a perfluoroorganometallic reagent for the introduction of the fluorous part. This compound is useful for biological studies and for imaging the ER alpha estradiol receptor distribution in the whole cell by secondary ion mass spectrometry (SIMS). The key step of this synthesis involves the radical reduction of an 11 beta-oxalate derivative. The stereochemical outcome of this reaction was studied for a range of C11 substituents, and we attempted to rationalize the apparent abnormal behavior of the phenyl group.

  DOI：

  10.1021/jo051424k

文献信息

• Synthesis of 11β-Perfluorohexylestradiol
  作者：Vangelis Agouridas、Jean-Claude Blazejewski、Emmanuel Magnier、Matthew E. Popkin

  DOI：10.1021/jo051424k

  日期：2005.10.1

  We report the synthesis of 11 beta-perfluorohexylestradiol le using a perfluoroorganometallic reagent for the introduction of the fluorous part. This compound is useful for biological studies and for imaging the ER alpha estradiol receptor distribution in the whole cell by secondary ion mass spectrometry (SIMS). The key step of this synthesis involves the radical reduction of an 11 beta-oxalate derivative. The stereochemical outcome of this reaction was studied for a range of C11 substituents, and we attempted to rationalize the apparent abnormal behavior of the phenyl group.