(+)-(2S,5S,6R)-1-aza-2-(3-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo[4.3.0]nonane | 209160-33-8

• 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,5S,6R)-1-aza-2-(3-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo[4.3.0]nonane
• 英文别名: (5S,8S,8aR)-5-(furan-3-yl)-8-methyl-5,6,8,8a-tetrahydro-1H-[1,3]oxazolo[3,4-a]pyridine-3,7-dione
• CAS: 209160-33-8
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: VFPKEMHYUAZOGB-HGNGGELXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(2S,5S,6R)-1-aza-2-(3-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo[4.3.0]nonane 在 palladium on activated charcoal sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 potassium tert-butylate 、 氢气 、 对甲苯磺酸 、 二甲基亚砜 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -65.0~110.0 ℃ 、101.33 kPa 条件下， 反应 64.0h， 生成 (5S,8R,9S)-(-)-5-(3-furyl)-8-methyloctahydroindolizidine
  参考文献：
  名称：

  Nuphar生物碱的对映选择性合成的新方法：（-）-（5S，8R，9S）-5-（3-Furyl）-8-甲基八氢吲哚并咪唑的第一全合成和（-）-Nupharamine的全合成。

  摘要：

  DOI：

  10.1021/jo9823240
• 作为产物：
  描述：

  三光气 、 (2R,3S,6S)-6-Furan-3-yl-2-hydroxymethyl-3-methyl-piperidin-4-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(+)-(2S,5S,6R)-1-aza-2-(3-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo[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.
• A Novel Approach to the Enantioselective Synthesis of Nuphar Alkaloids:  First Total Synthesis of (−)-(5<i>S</i>,8<i>R</i>,9<i>S</i>)-5- (3-Furyl)-8-methyloctahydroindolizidine and Total Synthesis of (−)-Nupharamine
  作者：José Barluenga、Fernando Aznar、Cristina Ribas、Carlos Valdés

  DOI：10.1021/jo9823240

  日期：1999.5.1