1-methoxy-6,7,8,8a-tetrahydro-5H-indolizin-3-one | 186135-52-4

• 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: 1-methoxy-6,7,8,8a-tetrahydro-5H-indolizin-3-one
• CAS: 186135-52-4
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: ISFYIUQUHDJQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methoxy-6,7,8,8a-tetrahydro-5H-indolizin-3-one 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 生成 1-Methoxy-5,6,7,8-tetrahydroindolizine
  参考文献：
  名称：

  通过还原取代的吡咯的立体选择性合成吡咯烷衍生物。

  摘要：

  研究了高度取代的吡咯体系的非均相催化加氢反应。这些芳族体系可通过出色的非对映选择性完全还原，从而获得具有多达四个新的立体中心的官能化吡咯烷。该反应很可能是两步氢化序列，C = X键的初始还原提供了一个立体中心，该中心指导吡咯的后续还原。

  DOI：

  10.1021/ol701962w
• 作为产物：
  描述：

  (三苯基膦烯)乙烯酮 、 2-哌啶甲酸甲酯 以 甲苯 为溶剂， 反应 12.0h， 以50%的产率得到1-methoxy-6,7,8,8a-tetrahydro-5H-indolizin-3-one
  参考文献：
  名称：

  Domino syntheses of five-, six- and seven-membered O-, N- and S-heterocycles from α-, β- and γ-substituted carboxylic esters

  摘要：

  By a one-pot procedure, tetronic acids, tetronates, coumarins, benzoxepinones and their N- and S-analogues are readily accessible from keteneylidene(triphenyl)phosphorane 2 and carboxylic esters bearing OH, NHR or SH groups in an alpha-, beta- or gamma-position by an addition/Wittig olefination/(Claisen rearrangement) sequence. This cascade can be controlled by temperature variation. Extension of this procedure by a further addition step yielding annulated bisheterocycles such as the furoquinolone 28 is possible in some cases.

  DOI：

  10.1039/p19960002799

文献信息

• Domino syntheses of five-, six- and seven-membered O-, N- and S-heterocycles from α-, β- and γ-substituted carboxylic esters
  作者：J. Löffler、R. Schobert

  DOI：10.1039/p19960002799

  日期：——

  By a one-pot procedure, tetronic acids, tetronates, coumarins, benzoxepinones and their N- and S-analogues are readily accessible from keteneylidene(triphenyl)phosphorane 2 and carboxylic esters bearing OH, NHR or SH groups in an alpha-, beta- or gamma-position by an addition/Wittig olefination/(Claisen rearrangement) sequence. This cascade can be controlled by temperature variation. Extension of this procedure by a further addition step yielding annulated bisheterocycles such as the furoquinolone 28 is possible in some cases.
• Stereoselective Synthesis of Pyrrolidine Derivatives via Reduction of Substituted Pyrroles
  作者：Chao Jiang、Alison J. Frontier

  DOI：10.1021/ol701962w

  日期：2007.11.1

  hydrogenation of highly substituted pyrrole systems was studied. These aromatic systems could be fully reduced with excellent diastereoselectivity to afford functionalized pyrrolidines with up to four new stereocenters. It is likely that the reaction is a two-step hydrogenation sequence, and that initial reduction of the C=X bond provides a stereocenter that directs the subsequent reduction of the pyrrole.

  研究了高度取代的吡咯体系的非均相催化加氢反应。这些芳族体系可通过出色的非对映选择性完全还原，从而获得具有多达四个新的立体中心的官能化吡咯烷。该反应很可能是两步氢化序列，C = X键的初始还原提供了一个立体中心，该中心指导吡咯的后续还原。