pristimerin dicyanophenalenedione | 1018838-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: pristimerin dicyanophenalenedione
• 英文别名: methyl (2R,5S,6R,8R,11S,14S)-18,19-dicyano-2,5,8,11,14-pentamethyl-22,23-dioxohexacyclo[15.7.1.02,15.05,14.06,11.021,25]pentacosa-1(24),15,17,19,21(25)-pentaene-8-carboxylate
• CAS: 1018838-16-8
• 化学式: C₃₄H₃₆N₂O₄
• 分子量: 536.671
• InChiKey: MNPBSJIEXFKPDL-ZIMIRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  扁塑藤素 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以4.8 mg的产率得到xuxuarin Eβ
  参考文献：
  名称：

  Biomimetic synthesis of xuxuarines Eα and Eβ: Structure revision of Rzedowskia bistriterpenoids

  摘要：

  Reaction of pristimerin with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a biomimetic-type coupling leading to xuxuarines E alpha and E beta and not the previously reported Rzedowskia bistriterpenoids I and II suggesting that the structures proposed for these natural products need revision. A product obtained in this reaction by an unusual Diels-Alder addition followed by retro-Diels-Alder-type elimination was characterized as pristimerin dicyanophenalenedione. Complete H-1, and C-13 NMR spectral assignments of xuxuarines Ea and Eb have been made by the application of 1D and 2D NMR techniques. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.008

文献信息

• Biomimetic synthesis of xuxuarines Eα and Eβ: Structure revision of Rzedowskia bistriterpenoids
  作者：Neil E. Jacobsen、E.M. Kithsiri Wijeratne、Joaquim Corsino、Maysa Furlan、Vanderlan da S. Bolzani、A.A. Leslie Gunatilaka

  DOI：10.1016/j.bmc.2007.11.008

  日期：2008.2.15

  Reaction of pristimerin with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a biomimetic-type coupling leading to xuxuarines E alpha and E beta and not the previously reported Rzedowskia bistriterpenoids I and II suggesting that the structures proposed for these natural products need revision. A product obtained in this reaction by an unusual Diels-Alder addition followed by retro-Diels-Alder-type elimination was characterized as pristimerin dicyanophenalenedione. Complete H-1, and C-13 NMR spectral assignments of xuxuarines Ea and Eb have been made by the application of 1D and 2D NMR techniques. (c) 2007 Elsevier Ltd. All rights reserved.