(2S,4R,6R)-6-tert-butyl-4-hydroxypiperidine-2-carboxylic acid | 1202852-53-6

• 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: (2S,4R,6R)-6-tert-butyl-4-hydroxypiperidine-2-carboxylic acid
• CAS: 1202852-53-6
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: MZWFPVKGJOVTLY-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,4R,6R)-6-tert-butyl-4-hydroxy-N-methylpiperidine-2-carboxamide 在 盐酸 、 水 作用下， 反应 30.0h， 以65%的产率得到(2S,4R,6R)-6-tert-butyl-4-hydroxypiperidine-2-carboxylic acid
  参考文献：
  名称：

  The Vinylfluoro Group as an Acetonyl Cation Equivalent: Stereoselective Synthesis of 6-Substituted 4-Hydroxy Pipecolic Acid Derivatives

  摘要：

  An unprecedented cascade of reactions after acid-catalyzed hydrolysis of tert-butyl (2S,5S)-2-tert-butyl-5-(2-fluoroallyl)-3-methyl-4-oxoimidazolidine-1-carboxylate 3a leading to pipecolic acid derivative 5 is presented. The vinylfluoro group is shown to be all acetonyl cation equivalent under acidic conditions. Interestingly, vinylchloro and vinylbromo groups do not show Such transformation under the same conditions. The pipecolic acid derivative 5 produced in this way is further used to synthesize (2R,4R,6S)-6-tert-butyl-4-hydroxypiperidine2-carboxylic acid 9.

  DOI：

  10.1021/jo901872a

文献信息

• The Vinylfluoro Group as an Acetonyl Cation Equivalent: Stereoselective Synthesis of 6-Substituted 4-Hydroxy Pipecolic Acid Derivatives
  作者：Nirupam Purkayastha、Deepak M. Shendage、Roland Fröhlich、Günter Haufe

  DOI：10.1021/jo901872a

  日期：2010.1.1

  An unprecedented cascade of reactions after acid-catalyzed hydrolysis of tert-butyl (2S,5S)-2-tert-butyl-5-(2-fluoroallyl)-3-methyl-4-oxoimidazolidine-1-carboxylate 3a leading to pipecolic acid derivative 5 is presented. The vinylfluoro group is shown to be all acetonyl cation equivalent under acidic conditions. Interestingly, vinylchloro and vinylbromo groups do not show Such transformation under the same conditions. The pipecolic acid derivative 5 produced in this way is further used to synthesize (2R,4R,6S)-6-tert-butyl-4-hydroxypiperidine2-carboxylic acid 9.