(2R,4S,6R)-1-benzyl-4-(methoxymethoxy)-6-methylpiperidine-2-carbaldehyde | 177341-49-0

• 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: (2R,4S,6R)-1-benzyl-4-(methoxymethoxy)-6-methylpiperidine-2-carbaldehyde
• CAS: 177341-49-0
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: AUTIZVHALLTKIF-BMFZPTHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1-辛基)三苯基溴化磷 、 (2R,4S,6R)-1-benzyl-4-(methoxymethoxy)-6-methylpiperidine-2-carbaldehyde 在 potassium tert-butylate 作用下， 生成 (2R,4S,6R)-1-benzyl-4-(methoxymethoxy)-2-methyl-6-[(Z)-non-1-enyl]piperidine 、 (2R,4S,6R)-1-benzyl-4-(methoxymethoxy)-2-methyl-6-[(E)-non-1-enyl]piperidine
  参考文献：
  名称：

  Enzymatic Route to Chiral, Nonracemic cis-2,6- and cis,cis-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D

  摘要：

  Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase(ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee greater than or equal to 98%). The general method is used to effect the synthesis of (+)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.

  DOI：

  10.1021/jo9519569
• 作为产物：
  描述：

  (2R,4S,6S)-2,6-Bis-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 159.5h， 生成 (2R,4S,6R)-1-benzyl-4-(methoxymethoxy)-6-methylpiperidine-2-carbaldehyde
  参考文献：
  名称：

  Enzymatic Route to Chiral, Nonracemic cis-2,6- and cis,cis-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D

  摘要：

  Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase(ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee greater than or equal to 98%). The general method is used to effect the synthesis of (+)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.

  DOI：

  10.1021/jo9519569

文献信息

• Enzymatic Route to Chiral, Nonracemic <i>cis</i>-2,6- and <i>cis</i>,<i>cis</i>-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D
  作者：Robert Chênevert、Michael Dickman

  DOI：10.1021/jo9519569

  日期：1996.1.1

  Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase(ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee greater than or equal to 98%). The general method is used to effect the synthesis of (+)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.