(2S,3S,6R)-6-ethyl-2-methylpiperidin-3-ol | 1356546-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,3S,6R)-6-ethyl-2-methylpiperidin-3-ol
• CAS: 1356546-03-6
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: DCHJCPWRAFDPMV-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 20 % Pd(OH)2/C 、 氢气 、 silica gel 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 (2S,3S,6R)-6-ethyl-2-methylpiperidin-3-ol
  参考文献：
  名称：

  从syn-(2R,1'S)-2-(1-Dibenzylaminomethyl)epoxide“all-cis”2-Methyl-6-Substituted Piperidin-3-ol生物碱的途径：(+)-Deoxocassine的快速全合成

  摘要：

  描述了导致合成两个顺-2-甲基-6-取代的哌啶-3-醇的一般策略。syn-(2R,1'S)-2-(1-Dibenzylaminomethyl) epoxide (13) 用作常见的结构单元。关键步骤涉及腙12a和12b的亲核氮杂-烯醇锂使13的环氧乙烷开环。随后的腙水解和分子内还原胺化以良好的产率提供了生物碱 (+)-deoxocassine 和该物质的新 C-6 乙基类似物。

  DOI：

  10.1002/ejoc.201101333

文献信息

• A Route to “all-cis” 2-Methyl-6-Substituted Piperidin-3-ol Alkaloids from syn-(2R,1′S)-2-(1-Dibenzylaminomethyl)epoxide: Rapid Total Synthesis of (+)-Deoxocassine
  作者：Pierre-Yves Géant、Jean Martínez、Xavier J. Salom-Roig

  DOI：10.1002/ejoc.201101333

  日期：2012.1

  to the synthesis of two cis-2-methyl-6-substituted piperidin-3-ols is described. syn-(2R,1′S)-2-(1-Dibenzylaminomethyl) epoxide (13) was used as common building block. The key step involved oxirane ring opening of 13 by the nucleophilic lithium aza-enolate of hydrazones 12a and 12b. Subsequent hydrazone hydrolysis and intramolecular reductive amination afforded the alkaloid (+)-deoxocassine and a new

  描述了导致合成两个顺-2-甲基-6-取代的哌啶-3-醇的一般策略。syn-(2R,1'S)-2-(1-Dibenzylaminomethyl) epoxide (13) 用作常见的结构单元。关键步骤涉及腙12a和12b的亲核氮杂-烯醇锂使13的环氧乙烷开环。随后的腙水解和分子内还原胺化以良好的产率提供了生物碱 (+)-deoxocassine 和该物质的新 C-6 乙基类似物。
• Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block
  作者：Pierre-Yves Géant、Erwann Grenet、Jean Martínez、Xavier J. Salom-Roig

  DOI：10.1016/j.tetasy.2015.11.008

  日期：2016.1

  gamma-N,N-Dibenzylamino-beta-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, I was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family. (C) 2015 Elsevier Ltd. All rights reserved.