methyl 8-((1S,2R,3aS,4S,7R,7aS)-3-oxo-2-((Z)-pent-2-en-1-yl)-2,3,3a,4,7,7ahexahydro-1H-4,7-methanoinden-1-yl)octanoate | 1439228-12-2

• 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: methyl 8-((1S,2R,3aS,4S,7R,7aS)-3-oxo-2-((Z)-pent-2-en-1-yl)-2,3,3a,4,7,7ahexahydro-1H-4,7-methanoinden-1-yl)octanoate
• 英文别名: methyl 8-[(1R,2S,3S,4R,6S,7S)-5-oxo-4-[(Z)-pent-2-enyl]-3-tricyclo[5.2.1.02,6]dec-8-enyl]octanoate
• CAS: 1439228-12-2
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: XSSUYTAFVLXGJL-XIZGZMDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 8-((1S,2R,3aS,4S,7R,7aS)-3-oxo-2-((Z)-pent-2-en-1-yl)-2,3,3a,4,7,7ahexahydro-1H-4,7-methanoinden-1-yl)octanoate 在 马来酸酐 、 甲基二氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.02h， 以54%的产率得到chromomoric acid B methyl ester
  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 、 sodium dihydrogenphosphate 、 正丁基锂 、 2,3-二甲基-2-丁烯 、 sodium chlorite 、 叔丁基锂 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 potassium iodide 、 三甲基硅烷化重氮甲烷 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 、 正戊烷 、 苯 为溶剂， 反应 57.17h， 生成 methyl 8-((1S,2R,3aS,4S,7R,7aS)-3-oxo-2-((Z)-pent-2-en-1-yl)-2,3,3a,4,7,7ahexahydro-1H-4,7-methanoinden-1-yl)octanoate
  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.