[(1S)-endo]-bornyl (S)-α-methoxy-α-trifluoromethylphenylacetate | 133625-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1S)-endo]-bornyl (S)-α-methoxy-α-trifluoromethylphenylacetate
• 英文别名: (-)-bornyl (S)-2-methoxy-2-(trifluoromethyl)phenylacetate
• CAS: 133625-35-1
• 化学式: C₂₀H₂₅F₃O₃
• 分子量: 370.412
• InChiKey: XGTQKQQJXMZZPN-SFUIVIKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  冰片 、 (R)-methoxytrifluoromethylphenylacetyl chloride 以 乙腈 为溶剂， 反应 1.5h， 生成 [(1S)-endo]-bornyl (S)-α-methoxy-α-trifluoromethylphenylacetate
  参考文献：
  名称：

  通过GC / MS解析异冰片及其异构体，以鉴定“合成的”和“半合成的”冰片产品。

  摘要：

  冰片是在传统中药中常用的植物萜烯。光学纯的（+）-冰片和（-）-冰片可分别从植物龙脑香科和印度苦瓜提取而得。“合成冰片”是从（±）-樟脑的还原反应中产生的，导致四种不同的立体异构体：（+）-异冰片醇，（-）-异冰片醇，（+）-冰片和（-）-冰片。相比之下，“半合成冰片”是由天然樟脑（+）-樟脑的还原生成的，可提供两种异构体：（-）-异冰片和（+）-冰片。我们通过使用两种手性试剂（R）-（+）-α-甲氧基-α-三氟甲基苯基乙酰氯（（R）-（+）-MTPA-Cl）和（1S）-（-）-氯化金。通过气相色谱分析由上述方法得到的衍生物。在本研究中，成功​​地从（+）-和（-）-冰片异构体中分离了（+）-和（-）-冰片醇的对映异构体，使其成为鉴定“合成的”和“半合成的”的有用方法冰片。此外，我们还研究了五种不同的商业冰片。在此过程中，观察到了一种从异冰片-山梨酸酯到冰片-山梨酸酯的新颖且前所未有的部分

  DOI：

  10.1002/chir.23017

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.