(R)-(-)-1-(4-chloro-2-pyridinyl)benzyl acetate | 896139-41-6

• 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: (R)-(-)-1-(4-chloro-2-pyridinyl)benzyl acetate
• CAS: 896139-41-6
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: IAWMRSATRWLTTE-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-(4-chloro-2-pyridinyl)benzyl acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (R)-(-)-4-chloro-2-(1-hydroxybenzyl)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
• 作为产物：
  描述：

  乙酸乙烯酯 、 (4-chloropyridin-2-yl)(phenyl)methanol 在 Pseudomonas cepacia lipase 作用下， 生成 (R)-(-)-4-chloro-2-(1-hydroxybenzyl)pyridine 、 (S)-(+)-4-chloro-[2-(1-hydroxybenzyl)pyridine] 、 (R)-(-)-1-(4-chloro-2-pyridinyl)benzyl acetate 、 (S)-(+)-1-(4-chloro-2-pyridinyl)benzyl acetate
  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