phenyl 4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: phenyl 4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate
• 英文别名: phenyl 4-hydroxy-3,4-dihydro-2H-quinoline-1-carboxylate
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: QCEAQCOPPAKVLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯乙酸乙烯酯 、 phenyl 4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate 在 Novozyme 435 lipase 作用下， 以 甲基叔丁基醚 为溶剂， 反应 8.0h， 以46%的产率得到(S)-phenyl 4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate
  参考文献：
  名称：

  Novozyme 435 lipase mediated enantioselective kinetic resolution: a facile method for the synthesis of chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol derivatives

  摘要：

  Vinyl 2-chloroacetate was used as an efficient acyl donor for enantioselective acylation of racemic 1,2,3,4-tetrahydroquinolin-4-ols and 2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ols with Novozyme 435 lipase. Two enantiocomplimentary tetrahydroquinolin-4-ol or tetrahydro-1H-benzo[b]azepin-5-ol derivatives could be smoothly obtained in good to excellent yields and ee values at the same time. Noteworthily, large scale preparation experiment was also demonstrated when amplified the reaction system to 10 g scale experiment, and products were obtained with high yields and ee values. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.066

文献信息

• Novozyme 435 lipase mediated enantioselective kinetic resolution: a facile method for the synthesis of chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol derivatives
  作者：Xiaojian Zhou、Daijun Zheng、Baodong Cui、Wenyong Han、Yongzheng Chen

  DOI：10.1016/j.tet.2015.05.066

  日期：2015.7

  Vinyl 2-chloroacetate was used as an efficient acyl donor for enantioselective acylation of racemic 1,2,3,4-tetrahydroquinolin-4-ols and 2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ols with Novozyme 435 lipase. Two enantiocomplimentary tetrahydroquinolin-4-ol or tetrahydro-1H-benzo[b]azepin-5-ol derivatives could be smoothly obtained in good to excellent yields and ee values at the same time. Noteworthily, large scale preparation experiment was also demonstrated when amplified the reaction system to 10 g scale experiment, and products were obtained with high yields and ee values. (C) 2015 Elsevier Ltd. All rights reserved.