(2S,3S,3aS,4R,7S,7aS)-2-(aminomethyl)-3-(8-hydroxyoctyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-one | 1439227-70-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3S,3aS,4R,7S,7aS)-2-(aminomethyl)-3-(8-hydroxyoctyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-one
• 英文别名: (1S,2S,4S,5S,6S,7R)-4-(aminomethyl)-5-(8-hydroxyoctyl)tricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 1439227-70-9
• 化学式: C₁₉H₃₁NO₂
• 分子量: 305.461
• InChiKey: DGWHNCHYUYGXOR-ZDRBWGSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,3aS,4R,7S,7aS)-2-(aminomethyl)-3-(8-hydroxyoctyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-one 在 咪唑 、 4-二甲氨基吡啶 、 sodium dihydrogenphosphate 、 正丁基锂 、 2,3-二甲基-2-丁烯 、 sodium chlorite 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 、 正戊烷 为溶剂， 反应 28.0h， 生成 8-((1S,2R,3aS,4S,7R,7aS)-3-oxo-2-((Z)-pent-2-en-1-yl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-yl)octanoic acid
  参考文献：
  名称：

  Pauson–Khand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones

  摘要：

  A new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine as an alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the alpha side chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.

  DOI：

  10.1021/ol400999a
• 作为产物：
  描述：

  8-溴-1-辛醇 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 叔丁基锂 、 potassium iodide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 、 正戊烷 为溶剂， 反应 28.42h， 生成 (2S,3S,3aS,4R,7S,7aS)-2-(aminomethyl)-3-(8-hydroxyoctyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-one
  参考文献：
  名称：

  Pauson–Khand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones

  摘要：

  A new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine as an alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the alpha side chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.

  DOI：

  10.1021/ol400999a

文献信息

• Pauson–Khand Adducts of <i>N</i>-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones
  作者：Nuria Aiguabella、Albert Pesquer、Xavier Verdaguer、Antoni Riera

  DOI：10.1021/ol400999a

  日期：2013.6.7

  A new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine as an alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the alpha side chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.