(-)-methyl Mosher ester | 26164-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-methyl Mosher ester
• 英文别名: methyl (S)-2-methoxy-2-(trifluoromethyl)phenylacetate；Methyl (S)-2-methoxy-2-phenyl-3,3,3-trifluoropropionate；methyl (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 26164-19-2
• 化学式: C₁₁H₁₁F₃O₃
• 分子量: 248.202
• InChiKey: RGACWXDYKJJHSQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-methyl Mosher ester 在 硫酸 作用下， 生成 (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸
  参考文献：
  名称：

  Optical rotatory dispersion studies. CXVII. Absolute configurational assignments of some .alpha.-substituted phenylacetic acids by circular dichroism measurements

  摘要：

  DOI：

  10.1021/ja00707a024
• 作为产物：
  描述：

  (S)-3,3,3-trifluoro-2-hydroxy-2-phenylpropanoic acid 在 silver(l) oxide 作用下， 生成 (-)-methyl Mosher ester
  参考文献：
  名称：

  Optical rotatory dispersion studies. CXVII. Absolute configurational assignments of some .alpha.-substituted phenylacetic acids by circular dichroism measurements

  摘要：

  DOI：

  10.1021/ja00707a024

文献信息

• Conversion of serine .beta.-lactones to chiral .alpha.-amino acids by copper-containing organolithium and organomagnesium reagents
  作者：Lee D. Arnold、John C. G. Drover、John C. Vederas

  DOI：10.1021/ja00249a031

  日期：1987.7

  Les amino-3 oxetannones-2 N-substituees et N,N-disubstituees reagissent avec des organocuprates pour donner des α-aminoacides

  Les amino-3 oxetannones-2 N-substituees et N,N-dissubstituees reagissent avec des Organocuprates pour donner des α-aminoacides
• Chapuis, C.; Bauer, T.; Jezewski, A., Polish Journal of Chemistry, 1994, vol. 68, # 11, p. 2323 - 2332
  作者：Chapuis, C.、Bauer, T.、Jezewski, A.、Jurczak, J.

  DOI：——

  日期：——
• Molecular mechanics calculations and comparison of proton, fluorine, and carbon NMR diastereomer discrimination via nonbonding interactions between fluorine-labeled enantiomeric amides and enantiomerically pure chiral solvating agents
  作者：Branko S. Jursic、Zoran Zdravkovski

  DOI：10.1021/jo00071a039

  日期：1993.9

  Diastereomer discrimination of fluorine-labeled enantiomers in chloroform solutions was studied with and without two chiral solvating agents (IS and 2S) using H-1, C-13, and F-19 NMR spectroscopy. Although by C-13 NMR spectroscopy the diastereomer discrimination is not observable, changes of chemical shifts for some carbon atoms unambiguously show formation of nonbonding interactions between the enantiomers and the chiral solvating agents. The position and the ratio of signal sets in both hydrogen and fluorine NMR spectra correspond to the enantiomeric composition in the solution. On the basis of changes in the chemical shifts of enantiomers in chloroform solutions of chiral solvating agent, binding constants and binding energy differences were calculated. Using the MM2 force field, calculations were performed on binding complexes between the chiral solvating agent 2S and enantiomers 6. It was shown that demand for energy differences between diastereomeric nonbonding complexes of racemic amides and the chiral solvating amides necessary to obtain their NMR diastereomer discrimination is low for H-1, intermediary for F-19, and high for C-13 NMR.
• ARNOLD, L. D.;DROVER, J. C. G.;VEDERAS, J. C., J. AMER. CHEM. SOC., 109,(1987) N 15, 4649-4659
  作者：ARNOLD, L. D.、DROVER, J. C. G.、VEDERAS, J. C.

  DOI：——

  日期：——
• Optical rotatory dispersion studies. CXVII. Absolute configurational assignments of some .alpha.-substituted phenylacetic acids by circular dichroism measurements
  作者：Guenter Barth、Wolfgang Voelter、Harry S. Mosher、Edward Bunnenberg、Carl Djerassi

  DOI：10.1021/ja00707a024

  日期：1970.2