[(1S,3S,4R,6S,9E,13E,15S)-4,9,13-trimethyl-18-methylidene-17-oxo-5,16-dioxatricyclo[13.3.0.04,6]octadeca-9,13-dien-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 122616-38-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: [(1S,3S,4R,6S,9E,13E,15S)-4,9,13-trimethyl-18-methylidene-17-oxo-5,16-dioxatricyclo[13.3.0.04,6]octadeca-9,13-dien-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 122616-38-0；122674-39-9
• 化学式: C₃₀H₃₅F₃O₆
• 分子量: 548.6
• InChiKey: NBOSUGOZTPNTBL-YLOFJPKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.36
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  Cembranolide A 在 4-二甲氨基吡啶 、 lithium hydroxide 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 [(1S,3S,4R,6S,9E,13E,15S)-4,9,13-trimethyl-18-methylidene-17-oxo-5,16-dioxatricyclo[13.3.0.04,6]octadeca-9,13-dien-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Absolute configurations of cytotoxic marine cembranolides; Consideration of mosher's method

  摘要：

  DOI：

  10.1016/s0040-4039(00)80593-6

文献信息

• High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids
  作者：Ikuko Ohtani、Takenori Kusumi、Yoel Kashman、Hiroshi Kakisawa

  DOI：10.1021/ja00011a006

  日期：1991.5

  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.
• KUSUMI, TAKENORI;OHTANI, IKUKO;INOUYE, YOSHINOBU;KAKISAWA, HIROSHI, TETRAHEDRON LETT., 29,(1988) N 37, C. 4731-4734
  作者：KUSUMI, TAKENORI、OHTANI, IKUKO、INOUYE, YOSHINOBU、KAKISAWA, HIROSHI

  DOI：——

  日期：——