(1S,8aR)-Octahydro-1-tert-butoxyindolizin-7-one | 167971-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1S,8aR)-Octahydro-1-tert-butoxyindolizin-7-one
• 英文别名: (1S,8aR)-1-[(2-methylpropan-2-yl)oxy]-2,3,5,6,8,8a-hexahydro-1H-indolizin-7-one
• CAS: 167971-88-2
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: WVZHUXXDZQJUEI-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,8aR)-Octahydro-1-tert-butoxyindolizin-7-one 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 (1R*,7R*,8aS*)-1,7-dihydroxyindolizidine
  参考文献：
  名称：

  A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine

  摘要：

  The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.

  DOI：

  10.1021/jo00120a016
• 作为产物：
  描述：

  1-{[(3S)-3-tert-butoxypyrrolidin-2-yl]methyl}cyclopropanol 在 tris(dibenzylideneacetone)dipalladium (0) 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以45%的产率得到(1S,8aR)-Octahydro-1-tert-butoxyindolizin-7-one
  参考文献：
  名称：

  Two-Step Metal-Mediated Transformation of Isoxazolidine-5-spirocyclopropanes into Pyridone Derivatives

  摘要：

  The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(O) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.

  DOI：

  10.1021/jo050640q

文献信息

• A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine
  作者：Stefano Cicchi、Andrea Goti、Alberto Brandi

  DOI：10.1021/jo00120a016

  日期：1995.7

  The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.
• Two-Step Metal-Mediated Transformation of Isoxazolidine-5-spirocyclopropanes into Pyridone Derivatives
  作者：Julia Revuelta、Stefano Cicchi、Alberto Brandi

  DOI：10.1021/jo050640q

  日期：2005.7.1

  The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(O) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.