Trifluoro-methanesulfonic acid (8S,9S,13S,14S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester | 845884-31-3

• 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: Trifluoro-methanesulfonic acid (8S,9S,13S,14S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester
• CAS: 845884-31-3
• 化学式: C₁₉H₂₃F₃O₃S
• 分子量: 388.451
• InChiKey: GWXBZIMWMVVMQK-BDXSIMOUSA-N

物化性质

• 熔点：
  51-52 °C
• 沸点：
  440.4±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (8S,9S,13S,14S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester 在 lithium chloride 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 2-((8S,9S,13S,14S)-13-Methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)-ethanol
  参考文献：
  名称：

  RCM-Based Synthesis of a Variety of β-C-Glycosides and Their in Vitro Anti-Solid Tumor Activity

  摘要：

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo040254t
• 作为产物：
  描述：

  雌酚酮 在 吡啶 、 三甲基氯硅烷 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 Trifluoro-methanesulfonic acid (8S,9S,13S,14S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  镍催化的芳基硒醇酯的分子内脱羰偶联

  摘要：

  该报告描述了一种镍催化的分子内脱羰偶联方法，该方法能够将芳烃烯醇酯转化为二芳基硒化物。廉价且容易获得的催化剂可以在温和的反应条件下用于构建结构多样的二芳基硒化物，包括杂环和天然产物衍生物。

  DOI：

  10.1002/adsc.202001611