(1S,2R,8R,8aR)-8-hydroxy-1,2-O-isopropylidene-1,2,3,5,8,8a-hexahydro-5-oxoindolizine | 909792-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,8R,8aR)-8-hydroxy-1,2-O-isopropylidene-1,2,3,5,8,8a-hexahydro-5-oxoindolizine
• 英文别名: (3aR,9R,9aR,9bS)-9-hydroxy-2,2-dimethyl-4,9,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
• CAS: 909792-19-4
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: IGDIIJSVPMKDMJ-KHUVANEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,8R,8aR)-8-hydroxy-1,2-O-isopropylidene-1,2,3,5,8,8a-hexahydro-5-oxoindolizine 在 sodium hydroxide 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 84.0h， 生成 (1S,2R,7R,8R,8aR)-7-acetylamino-1,2,8-trihydroxyindolizidine
  参考文献：
  名称：

  Stereoselective Michael Addition of Carbon-, Nitrogen-, Oxygen-, and Sulfur-Centered Nucleophiles on Enantiopure Hydroxylated 6,7-Dehydro-5-oxoindolizidine. Synthesis of Carbon- or Hetero-7-Substituted Swainsonine Analogues

  摘要：

  Enantiopure alpha beta-unsaturated delta-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines: (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.

  DOI：

  10.1021/jo060511p
• 作为产物：
  描述：

  (1S,2R,7R,8S,8aR)-1,2:7,8-di-O-isopropylidene-5-oxoindolizidine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以97%的产率得到(1S,2R,8R,8aR)-8-hydroxy-1,2-O-isopropylidene-1,2,3,5,8,8a-hexahydro-5-oxoindolizine
  参考文献：
  名称：

  Stereoselective Michael Addition of Carbon-, Nitrogen-, Oxygen-, and Sulfur-Centered Nucleophiles on Enantiopure Hydroxylated 6,7-Dehydro-5-oxoindolizidine. Synthesis of Carbon- or Hetero-7-Substituted Swainsonine Analogues

  摘要：

  Enantiopure alpha beta-unsaturated delta-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines: (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.

  DOI：

  10.1021/jo060511p

文献信息

• Stereoselective Michael Addition of Carbon-, Nitrogen-, Oxygen-, and Sulfur-Centered Nucleophiles on Enantiopure Hydroxylated 6,7-Dehydro-5-oxoindolizidine. Synthesis of Carbon- or Hetero-7-Substituted Swainsonine Analogues
  作者：Alessandro Tinarelli、Claudio Paolucci

  DOI：10.1021/jo060511p

  日期：2006.8.1

  Enantiopure alpha beta-unsaturated delta-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines: (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.