3'-farnesyl-2',4',6'-trihydroxyacetophenone | 183143-90-0

• 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: 3'-farnesyl-2',4',6'-trihydroxyacetophenone
• 英文别名: 1-[2,4,6-trihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]phenyl]ethanone
• CAS: 183143-90-0
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: NUSMNXVXTBPRRY-JTCWOHKRSA-N

物化性质

• 熔点：
  74-77 °C
• 沸点：
  533.0±50.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-farnesyl-2',4',6'-trihydroxyacetophenone 、 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86%的产率得到
  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
• 作为产物：
  描述：

  反,反-法呢基溴 、 2,4,6-三羟基苯乙酮一水合物 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以27%的产率得到3'-farnesyl-2',4',6'-trihydroxyacetophenone
  参考文献：
  名称：

  Mallatojaponin C及其相关化合物的合成及抗疟活性

  摘要：

  我们从前证明了来自Mallotus oppositifolius的间苯三酚Mallotojaponin C（1），由2'，4'，6'-三羟基苯乙酮和三个不同步骤合成了对疟原虫恶性疟原虫具有抗疟原虫和杀细胞活性。为了改善这类化合物的生物活性，合成了衍生物。发现两种衍生物，即简单的烯丙基化的间苯三酚12和13，具有与马洛托皂苷C相当的抗血浆活性。

  DOI：

  10.1021/acs.jnatprod.6b00347

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.
• Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds
  作者：Alexander L. Eaton、Seema Dalal、M. Belen Cassera、Shuqi Zhao、David G. I. Kingston

  DOI：10.1021/acs.jnatprod.6b00347

  日期：2016.6.24

  antiplasmodial and cytocidal activities against the malaria parasite Plasmodium falciparum, was synthesized in three steps from 2′,4′,6′-trihydroxyacetophenone, and various derivatives were synthesized in an attempt to improve the bioactivity of this class of compounds. Two derivatives, the simple prenylated phloroglucinols 12 and 13, were found to have comparable antiplasmodial activities to that of mallotojaponin

  我们从前证明了来自Mallotus oppositifolius的间苯三酚Mallotojaponin C（1），由2'，4'，6'-三羟基苯乙酮和三个不同步骤合成了对疟原虫恶性疟原虫具有抗疟原虫和杀细胞活性。为了改善这类化合物的生物活性，合成了衍生物。发现两种衍生物，即简单的烯丙基化的间苯三酚12和13，具有与马洛托皂苷C相当的抗血浆活性。