(-)-Menthyl (-)-(R)-α-O-methyl-α-(9-anthryl)acetate | 160727-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (-)-Menthyl (-)-(R)-α-O-methyl-α-(9-anthryl)acetate
• 英文别名: (-)-menthyl (R)-α-methoxy-α-(9-anthryl)acetate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R)-2-anthracen-9-yl-2-methoxyacetate
• CAS: 160727-75-3
• 化学式: C₂₇H₃₂O₃
• 分子量: 404.549
• InChiKey: RXRNZPVLRUURML-HPPBRVIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-Menthyl (-)-(R)-α-O-methyl-α-(9-anthryl)acetate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以51%的产率得到(-)-(R)-α-methoxy-α-(9-anthryl)acetic acid
  参考文献：
  名称：

  Myrioneurinol：一种来自Myrioneuron nutans的新型生物碱骨架

  摘要：

  一种新的生物碱，myrioneurinol（1），从叶片分离Myrioneuron碱草，其结构从波谱分析测定，包括质谱和二维核磁共振。Myrioneurinol（1）呈现了前所未有的融合四环骨架。通过改进的Mosher方法，使用（R）-和（S）-9-蒽甲氧基乙酸（9-AMAA）确定绝对构型。一种可能的生物合成途径从通过Δ-piperideine L-赖氨酸开始提出了1与nitraramine生物合成和相关生物碱比较。

  DOI：

  10.1016/j.tet.2007.08.095
• 作为产物：
  描述：

  9-Anthryl-2-oxoessigsaeure-ethylester 在 sodium tetrahydroborate 、 silver(l) oxide 作用下， 生成 (-)-Menthyl (-)-(R)-α-O-methyl-α-(9-anthryl)acetate
  参考文献：
  名称：

  Conformational Structure and Dynamics of Arylmethoxyacetates: DNMR Spectroscopy and Aromatic Shielding Effect

  摘要：

  The ground state conformational geometry and energy of esters of (R)- and (S)-arylmethoxyacetic acids were evaluated from low temperature H-1 and C-13 NMR spectra and by means of MM, AM1, and aromatic shielding effect calculations. In solution, the title compounds are constituted by two rotamers in equilibrium. Rotamer ap has the C-alpha-O and C=O bonds antiperiplanar and rotamer sp (lower in energy by 0.4-1.1 kcal/mol) has these bonds synperiplanar. In both the ap and the sp the aryl ring is ca. perpendicular to the C=O bond and coplanar with the CalphaH bond. Their relative populations and its temperature dependence evaluated by DNMR spectra are in agreement with the stereoselectivity reported for Diels-Alder reactions of dienyl-AMAA esters and support the ''perpendicular model'' proposed to account for that stereoselectivity. For conformations in which the aryl ring shields the alcohol moiety of the ester, calculated ring current shielding increments compare well with experimental shift values obtained from low-temperature NMR spectra and agree with the conformational model used in the Mislow-Dale-Mosher-Trost method for chiral recognition by NMR.

  DOI：

  10.1021/jo00108a008

文献信息

• Conformational Structure and Dynamics of Arylmethoxyacetates: DNMR Spectroscopy and Aromatic Shielding Effect
  作者：Sh. K. Latypov、J. M. Seco、E. Quinoa、R. Riguera

  DOI：10.1021/jo00108a008

  日期：1995.2

  The ground state conformational geometry and energy of esters of (R)- and (S)-arylmethoxyacetic acids were evaluated from low temperature H-1 and C-13 NMR spectra and by means of MM, AM1, and aromatic shielding effect calculations. In solution, the title compounds are constituted by two rotamers in equilibrium. Rotamer ap has the C-alpha-O and C=O bonds antiperiplanar and rotamer sp (lower in energy by 0.4-1.1 kcal/mol) has these bonds synperiplanar. In both the ap and the sp the aryl ring is ca. perpendicular to the C=O bond and coplanar with the CalphaH bond. Their relative populations and its temperature dependence evaluated by DNMR spectra are in agreement with the stereoselectivity reported for Diels-Alder reactions of dienyl-AMAA esters and support the ''perpendicular model'' proposed to account for that stereoselectivity. For conformations in which the aryl ring shields the alcohol moiety of the ester, calculated ring current shielding increments compare well with experimental shift values obtained from low-temperature NMR spectra and agree with the conformational model used in the Mislow-Dale-Mosher-Trost method for chiral recognition by NMR.
• Myrioneurinol: a novel alkaloid skeleton from Myrioneuron nutans
  作者：Van Cuong Pham、Akino Jossang、Thierry Sévenet、Van Hung Nguyen、Bernard Bodo

  DOI：10.1016/j.tet.2007.08.095

  日期：2007.11

  A new alkaloid, myrioneurinol (1), was isolated from the leaves of Myrioneuron nutans and its structure determined from spectral analysis, including mass spectrometry and 2D NMR. Myrioneurinol (1) presented an unprecedented fused tetracyclic skeleton. The absolute configuration was established by the modified Mosher's method, using (R)- and (S)-9-anthrylmethoxyacetic acid (9-AMAA). A plausible biosynthetic

  一种新的生物碱，myrioneurinol（1），从叶片分离Myrioneuron碱草，其结构从波谱分析测定，包括质谱和二维核磁共振。Myrioneurinol（1）呈现了前所未有的融合四环骨架。通过改进的Mosher方法，使用（R）-和（S）-9-蒽甲氧基乙酸（9-AMAA）确定绝对构型。一种可能的生物合成途径从通过Δ-piperideine L-赖氨酸开始提出了1与nitraramine生物合成和相关生物碱比较。