(1S,2S,6R,7R,8S)-7-(4-methoxyphenyl)-8-methyltetracyclo[5.5.2.01,8.02,6]tetradec-13-ene-3,5-dione | 166947-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,2S,6R,7R,8S)-7-(4-methoxyphenyl)-8-methyltetracyclo[5.5.2.01,8.02,6]tetradec-13-ene-3,5-dione
• CAS: 166947-38-2
• 化学式: C₂₂H₂₄O₃
• 分子量: 336.431
• InChiKey: AYEOVDPYHPFJMN-WIYBCGNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (1S,2S,6R,7R,8S)-7-(4-methoxyphenyl)-8-methyltetracyclo[5.5.2.01,8.02,6]tetradec-13-ene-3,5-dione 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 三甲基乙酰氯 、 三氟乙酸 作用下， 生成 (1S,3aS,3bS,7aS,8R,8aS)-1-butyl-8-(4-methoxyphenyl)-1,7a-dimethyl-1,2,3a,4,5,6,7,7a,8,8a-decahydro-3H-3b,8-ethenocyclopenta[a]inden-3-one
  参考文献：
  名称：

  Pure enantiomers from simple, symmetric dienophiles

  摘要：

  Starting from p-benzoquinone or 2-cyclopentene-1, 4-dione as dienophiles and the enantiomerically pure dienes 1a and 1b, high pressure cycloadditions led to chiral adducts. These were transformed in a regioselective manner to generate well defined stereogenic centres. A remarkably efficient electron density directed regioselectivity was discovered with 18c and 18d.

  DOI：

  10.1016/0957-4166(94)80092-8
• 作为产物：
  描述：

  4-环戊烯-1,3-二酮 、 (7aS)-1-(4-methoxyphenyl)-7a-methyl-4,5,6,7-tetrahydroindene 以 二氯甲烷 为溶剂， 25.0 ℃ 、700.0 MPa 条件下， 反应 24.0h， 以98%的产率得到(1S,2S,6R,7R,8S)-7-(4-methoxyphenyl)-8-methyltetracyclo[5.5.2.01,8.02,6]tetradec-13-ene-3,5-dione
  参考文献：
  名称：

  Pure enantiomers from simple, symmetric dienophiles

  摘要：

  Starting from p-benzoquinone or 2-cyclopentene-1, 4-dione as dienophiles and the enantiomerically pure dienes 1a and 1b, high pressure cycloadditions led to chiral adducts. These were transformed in a regioselective manner to generate well defined stereogenic centres. A remarkably efficient electron density directed regioselectivity was discovered with 18c and 18d.

  DOI：

  10.1016/0957-4166(94)80092-8

文献信息

• Pure enantiomers from simple, symmetric dienophiles
  作者：Pierre Riviere、Antony Mauvais、Ekkehard Winterfeldt

  DOI：10.1016/0957-4166(94)80092-8

  日期：1994.9

  Starting from p-benzoquinone or 2-cyclopentene-1, 4-dione as dienophiles and the enantiomerically pure dienes 1a and 1b, high pressure cycloadditions led to chiral adducts. These were transformed in a regioselective manner to generate well defined stereogenic centres. A remarkably efficient electron density directed regioselectivity was discovered with 18c and 18d.