(2S,6R)-6-tert-butyl-N-methyl-4-oxopiperidine-2-carboxamide | 1202852-49-0

• 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: (2S,6R)-6-tert-butyl-N-methyl-4-oxopiperidine-2-carboxamide
• CAS: 1202852-49-0
• 化学式: C₁₁H₂₀N₂O₂
• 分子量: 212.292
• InChiKey: SGUNWSDEDZKRAY-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,6R)-6-tert-butyl-N-methyl-4-oxopiperidine-2-carboxamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以86%的产率得到(2S,4R,6R)-6-tert-butyl-4-hydroxy-N-methylpiperidine-2-carboxamide
  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
• 作为产物：
  描述：

  tert-butyl (2S,5S)-2-tert-butyl-5-(2-fluoroallyl)-3-methyl-4-oxoimidazolidine-1-carboxylate 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以57%的产率得到(2S,6R)-6-tert-butyl-N-methyl-4-oxopiperidine-2-carboxamide
  参考文献：
  名称：

  有效获取具有哌啶骨架的构象刚性氨基酸类似物

  摘要：

  以对映体纯形式合成了两种具有哌啶骨架的非天然构象受限环状氨基酸衍生物。合成这些氨基酸的关键步骤是 4-氧代-哌啶酸衍生物中氧代基团的高度非对映选择性官能化。

  DOI：

  10.1055/s-0029-1219948

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.
• An Efficient Access to Conformationally Rigid Amino Acid Analogues with a Piperidine Skeleton
  作者：Günter Haufe、Nirupam Purkayastha

  DOI：10.1055/s-0029-1219948

  日期：2010.6

  Two unnatural conformationally constrained cyclic amino acid derivatives with the piperidine skeleton were synthesized in enantiomerically pure forms. The key step in the synthesis of these amino acids is the highly diastereoselective functionalization of the oxo group in a 4-oxo-pipecolic acid derivative.

  以对映体纯形式合成了两种具有哌啶骨架的非天然构象受限环状氨基酸衍生物。合成这些氨基酸的关键步骤是 4-氧代-哌啶酸衍生物中氧代基团的高度非对映选择性官能化。