2-(phenoxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(phenoxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one
• 英文别名: (1R,2R,6R,7S)-4-(phenoxymethyl)tricyclo[5.2.1.02,6]deca-4,8-dien-3-one
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: LUJZGOUOASYGMO-GUYJKWIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 2-(phenoxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one 在 四丁基氟化铵 作用下， 反应 24.0h， 以100%的产率得到2-(2-nitroethyl)-3-(nitromethyl)-2,3,3a,4,7,7ahexahydro-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
• 作为产物：
  描述：

  dicobalt octacarbonyl 、 苯基炔丙基醚 、 2,5-降冰片二烯 以 正己烷 、 甲苯 为溶剂， 反应 4.0h， 以71%的产率得到2-(phenoxymethyl)-3a,4,7,7a-tetrahydro-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.