(S)-(-)-4-(N,N-dimethylamino)-2-(1-hydroxyethyl)pyridine | 872036-49-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(-)-4-(N,N-dimethylamino)-2-(1-hydroxyethyl)pyridine
• 英文别名: (1S)-1-[4-(dimethylamino)pyridin-2-yl]ethanol
• CAS: 872036-49-2
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: MARYOPPKOGSZRK-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-4-(N,N-dimethylamino)-2-(1-hydroxyethyl)pyridine 在 18-冠醚-6 、 potassium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Biocatalytic preparation of optically active 4-(N,N-dimethylamino)pyridines for application in chemical asymmetric catalysis

  摘要：

  4-Chloro-2-(1-hydroxybenzyl)pyridine and 4-chloro-2-(1-hydroxyalkyl)pyridines were obtained with moderate to excellent enantiomeric excesses and high isolated yields by bioreduction with Baker's yeast of the corresponding ketones. The resulting optically active alcohols were transformed into adequate DMAP derivatives, which have been applied in asymmetric catalytic processes as nucleophilic catalysts in the stereoselective chemical alkoxycarbonylation of 1-phenylethanol or as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.018
• 作为产物：
  描述：

  2-acetyl-4-(N,N-dimethylamino)pyridine 在 Saccharomyces cerevisiae 、 葡萄糖 作用下， 以 水 为溶剂， 反应 168.0h， 以40%的产率得到(S)-(-)-4-(N,N-dimethylamino)-2-(1-hydroxyethyl)pyridine
  参考文献：
  名称：

  Biocatalytic preparation of optically active 4-(N,N-dimethylamino)pyridines for application in chemical asymmetric catalysis

  摘要：

  4-Chloro-2-(1-hydroxybenzyl)pyridine and 4-chloro-2-(1-hydroxyalkyl)pyridines were obtained with moderate to excellent enantiomeric excesses and high isolated yields by bioreduction with Baker's yeast of the corresponding ketones. The resulting optically active alcohols were transformed into adequate DMAP derivatives, which have been applied in asymmetric catalytic processes as nucleophilic catalysts in the stereoselective chemical alkoxycarbonylation of 1-phenylethanol or as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.018

文献信息

• Chemoenzymatic synthesis of chiral 4-(N,N-dimethylamino)pyridine derivatives
  作者：Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1016/j.tetasy.2005.09.006

  日期：2005.10

  Chiral 4-(N,N-dimethylamino)pyridine derivatives have been prepared through a chemoenzymatic synthesis where the enzymatic kinetic resolution of a family of 4-chloro-2-(1-hydroxyalkyl)pyridines is the key step for the formation of potentially important chiral catalysts. Pseudomonas cepacia lipase (PSL) showed excellent enantioselectivity in the acylation of the (R)-enantiomers (E > 200) using vinyl acetate as acylating agent and THF as solvent, obtaining products and substrates enantiomerically pure and with excellent yields. (c) 2005 Published by Elsevier Ltd.
• Biocatalytic preparation of optically active 4-(N,N-dimethylamino)pyridines for application in chemical asymmetric catalysis
  作者：Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1016/j.tetasy.2006.03.018

  日期：2006.3

  4-Chloro-2-(1-hydroxybenzyl)pyridine and 4-chloro-2-(1-hydroxyalkyl)pyridines were obtained with moderate to excellent enantiomeric excesses and high isolated yields by bioreduction with Baker's yeast of the corresponding ketones. The resulting optically active alcohols were transformed into adequate DMAP derivatives, which have been applied in asymmetric catalytic processes as nucleophilic catalysts in the stereoselective chemical alkoxycarbonylation of 1-phenylethanol or as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde. (c) 2006 Elsevier Ltd. All rights reserved.