3-Acetoxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester | 209865-54-3

• 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: 3-Acetoxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester
• 英文别名: phenyl 3-(acetyloxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 209865-54-3
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: DSZAVVAZCLCMQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Acetoxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 生成 (R)-3-Butyryloxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  A novel building block for the synthesis of isofagomin analogues

  摘要：

  The de novo synthesis of the novel potent building blocks phenyl (R)-3-acetoxymethyl-3,6-dihydro-2H-pyrid 1-carboxylate (-)-7 and phenyl (S)-3-butyryl-oxymethyl-3,6-dihydro-2H-pyridine-1-carboxylate (+)-8 starting from commercially available methyl-1-benzyl-4-oxo-3-piperidinecarboxylate is described. The key steps are the enantioselective esterification of the racemic alcohol 6 and the enantioselective hydrolysis of the racemic acetate 5, respectively, using lipase P from Pseudomonas caepacia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00090-1
• 作为产物：
  描述：

  (1-Benzyl-1,2,3,6-tetrahydro-pyridin-3-yl)-methanol 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 23.0h， 生成 3-Acetoxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  A novel building block for the synthesis of isofagomin analogues

  摘要：

  The de novo synthesis of the novel potent building blocks phenyl (R)-3-acetoxymethyl-3,6-dihydro-2H-pyrid 1-carboxylate (-)-7 and phenyl (S)-3-butyryl-oxymethyl-3,6-dihydro-2H-pyridine-1-carboxylate (+)-8 starting from commercially available methyl-1-benzyl-4-oxo-3-piperidinecarboxylate is described. The key steps are the enantioselective esterification of the racemic alcohol 6 and the enantioselective hydrolysis of the racemic acetate 5, respectively, using lipase P from Pseudomonas caepacia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00090-1