(1S,2R,7S,8aR)-7-dodecylsulfanyl-1,2-O-isopropylidene-5-oxoindolizidine

• 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,2R,7S,8aR)-7-dodecylsulfanyl-1,2-O-isopropylidene-5-oxoindolizidine
• 英文别名: (3aR,8S,9aR,9bS)-8-dodecylsulfanyl-2,2-dimethyl-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
• 化学式: C₂₃H₄₁NO₃S
• 分子量: 411.649
• InChiKey: PEMMXXABCRCFOJ-HIUFNZKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,2R,8aR)-(+)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5-oxoindolizine 在 sodium methylate 、 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 21.0h， 生成 (1S,2R,7S,8aR)-7-dodecylsulfanyl-1,2-O-isopropylidene-5-oxoindolizidine
  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.