(±)-sampsonin B

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (±)-sampsonin B
• 化学式: C₂₈H₃₂O₄
• 分子量: 432.56
• InChiKey: SMELKZQLHIEMMO-NKQBKRSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-异戊烯基-2,4,6-三羟基二苯甲酮 、 柠檬醛 在 ethylenediamine Tetraacetic Acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以88%的产率得到(±)-sampsonin B
  参考文献：
  名称：

  Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: application to 3′-prenylrubranine and petiolin D regioisomer

  摘要：

  Efficient synthetic routes for biologically interesting polycycles with prenylated, geranylated, and farnesylated citrans were developed from several trihydroxybenzenes with prenyl, geranyl, and farnesyl groups on the benzene rings. Ethylenediamine diacetate-catalyzed cyclization by a domino aldol-type/electrocyclization/H-shift/hetero Diels-Alder reaction of prenylated, geranylated, and farnesylated trihydroxybenzenes with citral or trans,trans-farnesal provided a variety of tetracycles bearing prenylated, geranylated, and farnesylated citrans. The mechanistic pathway for regio- and stereochemistry of synthesized polycycles was described. As an application of this methodology, 3'-prenylrubranine and petiolin D regioisomer were first synthesized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.075

文献信息

• Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: application to 3′-prenylrubranine and petiolin D regioisomer
  作者：Xue Wang、Yong Rok Lee

  DOI：10.1016/j.tet.2011.09.075

  日期：2011.11

  Efficient synthetic routes for biologically interesting polycycles with prenylated, geranylated, and farnesylated citrans were developed from several trihydroxybenzenes with prenyl, geranyl, and farnesyl groups on the benzene rings. Ethylenediamine diacetate-catalyzed cyclization by a domino aldol-type/electrocyclization/H-shift/hetero Diels-Alder reaction of prenylated, geranylated, and farnesylated trihydroxybenzenes with citral or trans,trans-farnesal provided a variety of tetracycles bearing prenylated, geranylated, and farnesylated citrans. The mechanistic pathway for regio- and stereochemistry of synthesized polycycles was described. As an application of this methodology, 3'-prenylrubranine and petiolin D regioisomer were first synthesized. (C) 2011 Elsevier Ltd. All rights reserved.