3-geranyl-2,4,6-trihydroxybenzophenone | 70219-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-geranyl-2,4,6-trihydroxybenzophenone
• 英文别名: [3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4,6-trihydroxyphenyl]-phenylmethanone
• CAS: 70219-87-3
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: ZAIQNYMNZNXUAF-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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-geranyl-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 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：

  2,4,6-三甲氧基苯甲酮 在 三溴化硼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 3-geranyl-2,4,6-trihydroxybenzophenone
  参考文献：
  名称：

  Synthesis of 3-geranyl- and 3-prenyl-2,4,6-trihydroxybenzophenone

  摘要：

  Biologically active phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone (2) and phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (3) were synthesized by an efficient and convenient synthetic sequence. The reaction steps of this synthesis included methylation, Friedel-Crafts acylation, demethylation and geranylation steps.

  DOI：

  10.1080/00397911.2016.1276603

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• <i>gem</i>-Diprenylation of Acylphloroglucinols by a Fungal Prenyltransferase of the Dimethylallyltryptophan Synthase Superfamily
  作者：Kang Zhou、Carsten Wunsch、Jungui Dai、Shu-Ming Li

  DOI：10.1021/acs.orglett.6b03594

  日期：2017.1.20

  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.
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
• 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 of 3-geranyl- and 3-prenyl-2,4,6-trihydroxybenzophenone
  作者：Vuyisa Mzozoyana、Fanie R. van Heerden

  DOI：10.1080/00397911.2016.1276603

  日期：2017.3.19

  Biologically active phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone (2) and phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (3) were synthesized by an efficient and convenient synthetic sequence. The reaction steps of this synthesis included methylation, Friedel-Crafts acylation, demethylation and geranylation steps.