methyl (2R,5R)-5-benzoyloxy-N-methoxycarbonyl-piperidine-2-carboxylate | 154049-34-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,5R)-5-benzoyloxy-N-methoxycarbonyl-piperidine-2-carboxylate
• 英文别名: dimethyl (2R,5R)-5-benzoyloxypiperidine-1,2-dicarboxylate
• CAS: 154049-34-0
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: VYTXIEAOCYTMSQ-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R,5R)-5-benzoyloxy-N-methoxycarbonyl-piperidine-2-carboxylate 在 盐酸 作用下， 反应 6.0h， 以59%的产率得到(2R,5R)-5-hydroxypipecolic acid hydrochloride
  参考文献：
  名称：

  Synthesis of 2S,5S-and 2R,5S-5-hydroxypipecolic acid via amide-methylenation of S-5-hydroxy-2-piperidone with dimethyltitanocene.

  摘要：

  A route to 2S,5S-and 2R,5S-hydroxypipecolic acid is presented, starting with the enantiopure 5S-5-hydroxy-piperidone 7. The key step of this reaction sequence is the chemoselective methylenation of the amide carbonyl group of 8 with dimethyltitanocene 9 to 10. The transformation of the exocyclic enecarbamate double bond to the carboxylic acid group is best accomplished via hydroboration/oxidation to the alcohol 11a,b. Separation and oxidation of the diastereomers 11a,b, to 14a, and 14b, and hydrolysis furnishes the diastereomeric pipecolic acids 15a and 15b in enantiopure form.

  DOI：

  10.1016/s0957-4166(00)82257-0
• 作为产物：
  描述：

  methyl (2R,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-piperidine-2-carboxylate 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 49.0h， 生成 methyl (2R,5R)-5-benzoyloxy-N-methoxycarbonyl-piperidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of 2S,5S-and 2R,5S-5-hydroxypipecolic acid via amide-methylenation of S-5-hydroxy-2-piperidone with dimethyltitanocene.

  摘要：

  A route to 2S,5S-and 2R,5S-hydroxypipecolic acid is presented, starting with the enantiopure 5S-5-hydroxy-piperidone 7. The key step of this reaction sequence is the chemoselective methylenation of the amide carbonyl group of 8 with dimethyltitanocene 9 to 10. The transformation of the exocyclic enecarbamate double bond to the carboxylic acid group is best accomplished via hydroboration/oxidation to the alcohol 11a,b. Separation and oxidation of the diastereomers 11a,b, to 14a, and 14b, and hydrolysis furnishes the diastereomeric pipecolic acids 15a and 15b in enantiopure form.

  DOI：

  10.1016/s0957-4166(00)82257-0