(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 125417-17-6

• 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: (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• CAS: 125417-17-6
• 化学式: C₃₈H₅₁F₃O₃
• 分子量: 612.816
• InChiKey: RUZZEWFXFSELFA-DJNVQCOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.99
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  麦角固醇 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 13.0h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids

  摘要：

  Mosher's (H-1) method to elucidate the absolute configuration of secondary alcohols was reexamined by use of high-field FT NMR spectroscopy, which enables assignment of most of the protons of complex molecules. There is a systematic arrangement of DELTA-delta (delta-S - delta-R) values obtained for the (R)- and (S)-MTPA esters of (-)-menthol, (-)-borneol, cholesterol, and ergosterol, the absolute configurations of which are known. Analysis of the DELTA-delta values of these compounds led to a rule that could predict the absolute configurations of natural products. When this rule was applied to some marine terpenoids including cembranolides and xenicanes, their absolute configurations were assigned and a part of the results were confirmed by X-ray structural analyses. In the case of sipholenol A, which has a sterically hindered OH group, this rule is inapplicable. But the problem is overcome by inverting the OH group to a less sterically hindered position; the resulting epimer gives systematically arranged DELTA-delta values, which enabled the elucidation of the absolute configuration. Comparison of the present method with Mosher's F-19 method indicates that the latter one using F-19 NMR lacks in reliability.

  DOI：

  10.1021/ja00011a006