(1S,2S,8aS)-1,2-di(tert-butoxy)-2,3,6,8a-tetrahydro-5-(1H)-indolizinone | 863890-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S,2S,8aS)-1,2-di(tert-butoxy)-2,3,6,8a-tetrahydro-5-(1H)-indolizinone
• 英文别名: (1S,2S,8aS)-1,2-bis[(2-methylpropan-2-yl)oxy]-2,3,6,8a-tetrahydro-1H-indolizin-5-one
• CAS: 863890-66-8
• 化学式: C₁₆H₂₇NO₃
• 分子量: 281.395
• InChiKey: MDJKMCVRDMVRMO-OBJOEFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,8aS)-1,2-di(tert-butoxy)-2,3,6,8a-tetrahydro-5-(1H)-indolizinone 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (+)-lentiginosine
  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：

  (3S,4S)-3,4-di-tert-butoxy-1-pyrroline N-oxide 在 Grubbs catalyst first generation indium 、 氯化铵 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 71.75h， 生成 (1S,2S,8aS)-1,2-di(tert-butoxy)-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.