3a,4,9,9a-tetrahydro-2-(p-methoxyphenyl)-4,9-[1’,2’]benzeno-1H-benz[f]isoindole-1,3-(2H)-dione

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 3a,4,9,9a-tetrahydro-2-(p-methoxyphenyl)-4,9-[1’,2’]benzeno-1H-benz[f]isoindole-1,3-(2H)-dione
• 英文别名: (15S,19R)-17-(4-methoxyphenyl)-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• 化学式: C₂₅H₁₉NO₃
• 分子量: 381.431
• InChiKey: JTNKBADCKDMOCB-MYNGYRLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3a,4,9,9a-tetrahydro-2-(p-methoxyphenyl)-4,9-[1’,2’]benzeno-1H-benz[f]isoindole-1,3-(2H)-dione 在 硼烷四氢呋喃络合物 、 对甲苯磺酸 、 cis-2-methoxy-indano[1,2-d][1,3,2]oxazaborolidine 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (3R,3aS,9aR)-2,3,3a,4,9,9a-hexahydro-3-methoxy-2-(4-methoxyphenyl)-4,9-[1',2']benzeno-1H-benz[f]isoindol-1-one
  参考文献：
  名称：

  Enantioselective Catalytic Desymmetrization of Maleimides by Temporary Removal of an Internal Mirror Plane and Stereoablative Over-reduction: Synthesis of (R)-Pyrrolam A

  摘要：

  A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.

  DOI：

  10.1021/ol5016702
• 作为产物：
  描述：

  甲氧苯胺 以 甲苯 为溶剂， 反应 10.67h， 生成 3a,4,9,9a-tetrahydro-2-(p-methoxyphenyl)-4,9-[1’,2’]benzeno-1H-benz[f]isoindole-1,3-(2H)-dione
  参考文献：
  名称：

  Enantioselective Catalytic Desymmetrization of Maleimides by Temporary Removal of an Internal Mirror Plane and Stereoablative Over-reduction: Synthesis of (R)-Pyrrolam A

  摘要：

  A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.

  DOI：

  10.1021/ol5016702

文献信息

• Enantioselective Catalytic Desymmetrization of Maleimides by Temporary Removal of an Internal Mirror Plane and Stereoablative Over-reduction: Synthesis of (<i>R</i>)-Pyrrolam A
  作者：Barrie J. Marsh、Harry Adams、Mike D. Barker、Ibrahim U. Kutama、Simon Jones

  DOI：10.1021/ol5016702

  日期：2014.7.18

  A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.