(-)-(2S,4R,5S,6R)-1-aza-2-(3-furyl)-4-hydroxy-5-methyl-8-oxa-9-oxobicyclo[4.3.0]nonane | 209160-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (-)-(2S,4R,5S,6R)-1-aza-2-(3-furyl)-4-hydroxy-5-methyl-8-oxa-9-oxobicyclo[4.3.0]nonane
• 英文别名: (5S,7R,8S,8aR)-5-(furan-3-yl)-7-hydroxy-8-methyl-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 209160-35-0
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: OTPSGILZGJTHKG-DMLMCSCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(2S,4R,5S,6R)-1-aza-2-(3-furyl)-4-hydroxy-5-methyl-8-oxa-9-oxobicyclo[4.3.0]nonane 在 sodium hydroxide 、 草酰氯 、 双氧水 、 氧气 、 sodium hydride 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414
• 作为产物：
  描述：

  (2R,3S,6S)-6-Furan-3-yl-2-hydroxymethyl-3-methyl-piperidin-4-one 在 sodium hydroxide 、 双氧水 、 potassium tri-sec-butyl-borohydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 (-)-(2S,4R,5S,6R)-1-aza-2-(3-furyl)-4-hydroxy-5-methyl-8-oxa-9-oxobicyclo[4.3.0]nonane
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414

文献信息

• Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives
  作者：José Barluenga、Fernando Aznar、Carlos Valdés、Cristina Ribas

  DOI：10.1021/jo9722414

  日期：1998.6.1

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.