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 | 1439228-06-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 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
• CAS: 1439228-06-4
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: JQGDJPQSYWXUNE-QMIHIPRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  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 在 马来酸酐 、 甲基二氯化铝 、 三甲基硅烷化重氮甲烷 作用下， 以 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 0.77h， 生成 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-((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)octanal 在 sodium dihydrogenphosphate 、 2,3-二甲基-2-丁烯 、 sodium chlorite 作用下， 以 水 、 叔丁醇 为溶剂， 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