3-Hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester | 209865-55-4

• 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-Hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester
• 英文别名: phenyl 3-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 209865-55-4
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: AYYCSUKVOCBYHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  正丁酸乙烯酯 、 3-Hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester 以 正己烷 、 二氯甲烷 为溶剂， 生成 (S)-3-Butyryloxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester 、 (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-苄基-3-甲氧基羰酰-4-哌啶酮 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 33.0h， 生成 3-Hydroxymethyl-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

文献信息

• A novel building block for the synthesis of isofagomin analogues
  作者：Hans-Josef Altenbach、Gaetano Blanda

  DOI：10.1016/s0957-4166(98)00090-1

  日期：1998.5

  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.