3-farnesyl-2,4,6-trihydroxybenzophenone | 1345984-33-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 3-farnesyl-2,4,6-trihydroxybenzophenone
• 英文别名: phenyl-[2,4,6-trihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]phenyl]methanone
• CAS: 1345984-33-9
• 化学式: C₂₈H₃₄O₄
• 分子量: 434.576
• InChiKey: RQXRNAMUZBUIMY-FJNYLYSMSA-N

物化性质

• 沸点：
  590.9±39.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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-trihydroxybenzophenone 、 柠檬醛 在 ethylenediamine Tetraacetic Acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以85%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：

  2,4,6-三羟基二苯甲酮 、 farnesyl pyrophosphate 在 Aspergillus terreus aromatic prenyltransferase 、 calcium chloride 作用下， 以 二甲基亚砜 、 甘油 为溶剂， 反应 2.0h， 以4.67%的产率得到3-farnesyl-2,4,6-trihydroxybenzophenone
  参考文献：
  名称：

  gem-Diprenylation of Acylphloroglucinols by a Fungal Prenyltransferase of the Dimethylallyltryptophan Synthase Superfamily

  摘要：

  Aspergillus terreus aromatic prenyltransferase (AtaPT) catalyzes predominantly C-monoprenylation of acylphloroglucinols in the presence of different prenyl diphosphates. With dimethylallyl diphosphate (DMAPP) as prenyl donor, gem-diprenylated products 1D3, 2D3, and 3D3 were also detected. High conversion of 1D1 to 1D3, 2D1 to 2D3, and 3D1 to 3D3 was demonstrated by incubation with AtaPT and DMAPP. The first example of gem-diprenylation by a member of the dimethylallyltryptophan synthase superfamily is provided.

  DOI：

  10.1021/acs.orglett.6b03594