(R)-2-Hydroxy-pentanoic acid anthracen-9-ylmethyl ester | 197309-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (R)-2-Hydroxy-pentanoic acid anthracen-9-ylmethyl ester
• CAS: 197309-71-0
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: MTOBAEUECQHPCC-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2-萘甲酰基)咪唑 、 (R)-2-Hydroxy-pentanoic acid anthracen-9-ylmethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 [(2R)-1-(anthracen-9-ylmethoxy)-1-oxopentan-2-yl] naphthalene-2-carboxylate
  参考文献：
  名称：

  Enzymatic Resolution of Chiral 2-Hydroxy Carboxylic Acids by Enantioselective Oxidation with Molecular Oxygen Catalyzed by the Glycolate Oxidase from Spinach (Spinacia oleracea)

  摘要：

  The enzymatic oxidation of a variety of saturated and unsaturated aliphatic derivatives of racemic 2-hydroxy acids 1 to their 2-oxo acids 2 with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) was shown to proceed highly enantioselectively. Thus, the glycolate oxidase-catalyzed kinetic resolution provides a convenient biocatalytic method for the preparation of enantiomerically pure (R)-2-hydroxy acids. The absolute configuration of tbe (R)-2-hydroxy acid Ib was assigned by comparison of the measured optical rotation value with that of the literature data and by application of the exciton-coupled circular dichroism method (ECCD) on its bichromophoric 2-naphthoate 9-methylanthryl derivative 3b. These results establish the ECCD method as a convenient microscale chirooptic tool for the configurational assignment of 2-hydroxy acids.

  DOI：

  10.1021/jo971298n
• 作为产物：
  描述：

  2-羟基戊酸 在 glycolate oxidase from Spinacia oleracea 、 氧气 、 乙二胺 、 2,6-蒽二酚 作用下， 以 乙醚 、 水 为溶剂， 反应 22.5h， 生成 (R)-2-Hydroxy-pentanoic acid anthracen-9-ylmethyl ester
  参考文献：
  名称：

  Enzymatic Resolution of Chiral 2-Hydroxy Carboxylic Acids by Enantioselective Oxidation with Molecular Oxygen Catalyzed by the Glycolate Oxidase from Spinach (Spinacia oleracea)

  摘要：

  The enzymatic oxidation of a variety of saturated and unsaturated aliphatic derivatives of racemic 2-hydroxy acids 1 to their 2-oxo acids 2 with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) was shown to proceed highly enantioselectively. Thus, the glycolate oxidase-catalyzed kinetic resolution provides a convenient biocatalytic method for the preparation of enantiomerically pure (R)-2-hydroxy acids. The absolute configuration of tbe (R)-2-hydroxy acid Ib was assigned by comparison of the measured optical rotation value with that of the literature data and by application of the exciton-coupled circular dichroism method (ECCD) on its bichromophoric 2-naphthoate 9-methylanthryl derivative 3b. These results establish the ECCD method as a convenient microscale chirooptic tool for the configurational assignment of 2-hydroxy acids.

  DOI：

  10.1021/jo971298n