methyl (2S,6S)-2-ethanoate | 225089-27-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: methyl (2S,6S)-2-ethanoate
• CAS: 225089-27-0
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: GOSDUNGDIPALAG-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,6S)-2-ethanoate 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以98%的产率得到methyl (2S,6S)-2-(2-hydroxyethyl)-6-propylpiperidine-1-carboxylate
  参考文献：
  名称：

  Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

  摘要：

  The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent lambda(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00073-3
• 作为产物：
  描述：

  methyl (1R,2R,4S,6S)-3-methyl-4-(trimethylsilyloxy)-10-azatricyclo<4.3.1.0^2,4>decane-10-carboxylate 在 palladium on activated charcoal 三氟甲磺酸 、 氢气 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 为溶剂， 反应 48.08h， 生成 methyl (2S,6S)-2-ethanoate
  参考文献：
  名称：

  Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

  摘要：

  The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent lambda(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00073-3