(1S,2S,8aS)-1,2-diacetyloxy-2,3,6,8a-tetrahydro-5(1H)-indolizinone | 863890-73-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,8aS)-1,2-diacetyloxy-2,3,6,8a-tetrahydro-5(1H)-indolizinone
• 英文别名: [(1S,2S,8aS)-1-acetyloxy-5-oxo-2,3,6,8a-tetrahydro-1H-indolizin-2-yl] acetate
• CAS: 863890-73-7
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: BHNDKCPPDJBQQC-NHCYSSNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,8aS)-1,2-diacetyloxy-2,3,6,8a-tetrahydro-5(1H)-indolizinone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以92 mg的产率得到(1S,2S,8aS)-1,2-diacetyloxy-hexahydro-5(1H)-indolizinone
  参考文献：
  名称：

  New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues

  摘要：

  An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

  DOI：

  10.1021/jo0509408
• 作为产物：
  描述：

  (2S,3S,4S)-3,4-diacetyloxy-1-(3-butenoyl)-2-vinylpyrrolidine 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以275 mg的产率得到(1S,2S,8aS)-1,2-diacetyloxy-2,3,6,8a-tetrahydro-5(1H)-indolizinone
  参考文献：
  名称：

  New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues

  摘要：

  An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

  DOI：

  10.1021/jo0509408

文献信息

• New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues
  作者：Francesca Cardona、Guillermo Moreno、Francesco Guarna、Pierre Vogel、Catherine Schuetz、Pedro Merino、Andrea Goti

  DOI：10.1021/jo0509408

  日期：2005.8.1

  An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.