3-异戊烯基-2,4,6-三羟基二苯甲酮 | 93796-20-4

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-异戊烯基-2,4,6-三羟基二苯甲酮
• 英文名称: phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone
• 英文别名: 3-Prenyl-2,4,6-trihydroxybenzophenone；phenyl-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
• CAS: 93796-20-4
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: WKFZVPVRFGJMEY-UHFFFAOYSA-N

物化性质

• 熔点：
  102–103°C
• 沸点：
  461.0±24.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2914400090
• 储存条件：
  存储条件：2-8℃，干燥，密封。

反应信息

• 作为反应物：
  描述：

  3-异戊烯基-2,4,6-三羟基二苯甲酮 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 12.0h， 生成 2,4,6-trihydroxy-3-isopentyl-5-(3-methylbut-2-enyl)benzophenone
  参考文献：
  名称：

  Cann, Martin R.; Davis, Anne-Marie; Shannon, Patrick V. R., Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1413 - 1421

  摘要：

  DOI：
• 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 24.0h， 生成 3-异戊烯基-2,4,6-三羟基二苯甲酮
  参考文献：
  名称：

  含氟异戊二烯化二苯甲酮的合成

  摘要：

  摘要 本研究开发了一种合成含氟异戊二苯甲酮的有效途径。Friedel-Crafts 酰化和亲电芳香取代反应是该合成获得这些氟化异戊二烯化二苯甲酮的关键反应。在异戊二烯化步骤中使用 DBU 仅获得 C-异戊二烯化二苯甲酮，而 K2CO3 产生 C-和 O-异戊二烯化二苯甲酮。图形概要

  DOI：

  10.1080/00397911.2020.1771597

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）。
• Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives
  作者：Solenn Brajeul、Bernard Delpech、Christian Marazano

  DOI：10.1016/j.tetlet.2007.06.042

  日期：2007.8

  In search for new methods aiming biomimetic synthesis of polyprenylated acylphloroglucinols (PPAPs), we now report the results of an evaluation of sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives, in neutral conditions. As a result, conditions were found for rather efficient C-prenylation of these compounds. The corresponding trimethyl ether gave the best results, but the reaction was accompanied by a deacylation process. Geranyl transfer was also observed, but in low yield, and, interestingly, an isolavandulyl group could be introduced with an appreciable yield. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.
• Friedel–Crafts Alkylation of Acylphloroglucinols Catalyzed by a Fungal Indole Prenyltransferase
  作者：Kang Zhou、Lena Ludwig、Shu-Ming Li

  DOI：10.1021/np5009784

  日期：2015.4.24

  Naturally occurring prenylated acylphloroglucinol derivatives are plant metabolites with diverse biological and pharmacological activities: Prenylation of acylphloroglucinols plays an important role in the formation of these intriguing natural products and is catalyzed in plants by membrane-bound enzymes. In this study, we demonstrate the prenylation of such compounds by a soluble fungal prenyltransferase AnaPT involved in the biosynthesis of prenylated indole alkaloids. The observed activities of AnaPT toward these substrates are Much higher than that of a microsomal fraction containing an overproduced prenyltransferase from the plant hop.
• <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.