clusiaphenone B | 70219-84-0

• 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: clusiaphenone B
• 英文别名: 2,4,6-trihydroxy-3,5-diprenylbenzophenone；phenyl-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]methanone
• CAS: 70219-84-0
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: DGDGUAUJFQUJRX-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95°C
• 沸点：
  529.9±50.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  6
• 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：

  clusiaphenone B 在 palladium on activated charcoal 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成 2-benzoyl-3,5-dihydroxy-4,6-diisopentyl-4-(3-methylbut-3-en-1-yl)cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Biomimetic Total Synthesis of (±)-Doitunggarcinone A and (+)-Garcibracteatone

  摘要：

  A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.

  DOI：

  10.1021/jo500027k
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲酮 在 氢碘酸 、 sodium methylate 作用下， 以 甲醇 、 乙酸酐 为溶剂， 反应 7.0h， 生成 clusiaphenone B
  参考文献：
  名称：

  Pathak, V. P.; Khanna, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 3, p. 253 - 254

  摘要：

  DOI：

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）。
• Synthesis of fluorine-containing prenylated benzophenones
  作者：Vuyisa Mzozoyana、Fanie R. van Heerden

  DOI：10.1080/00397911.2020.1771597

  日期：2020.7.17

  fluorine-containing prenylated benzophenones was developed. Friedel–Crafts acylation and electrophilic aromatic substitution reactions were the key reactions of this synthesis to achieve these fluorinated prenylated benzophenones. The use of DBU in the prenylation step achieved only the C-prenylated benzophenones, whereas K2CO3 produced the C- and O-prenylated benzophenones. Graphical Abstract

  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
• Synthesis of Naturally Occurring Prenylated Benzophenones. Vismiaphenone A, Vismiaphenone B, and Isovismiaphenone B
  作者：Ved Prakash Pathak、Rajinder Nath Khanna

  DOI：10.1246/bcsj.55.2264

  日期：1982.7

  2,4,6-Trihydroxybenzophenone on prenylation with 2-methyl-3-buten-2-ol in the presence of (C2H5)2O·BF3 yielded 2,4,6-trihydroxy-3,5-diprenylbenzophenone (3), 2,6-dihydroxy-4-prenyloxybenzophenone, 2,6-dihydroxy-3-prenyl-4-prenyloxybenzophenone, a benzodipyran and 6-benzoyl-5,7-dihydroxy-2,2-dimethyl-3-prenylchroman. 3 on reaction with 2 moles of p-toluenesulfonyl chloride followed by methylation and detosylation gave a naturally occurring benzophenone, vismiaphenone A (12). Cyclodehydrogenation of 6-hydroxy-3,5-diprenyl-2,4-ditosyloxybenzophenone gave 8-benzoyl-2,2-dimethyl-6-prenyl-5,7-ditosyloxy-2H-1-benzopyran, which on detosylation gave another naturally occurring benzophenone, isovismiaphenone B, while cyclodehydrogenation of 3 gave vismiaphenone B, another naturally occurring benzophenone. 2,4-Dihydroxy-6-methoxy-benzophenone on similar treatment with 2-methyl-3-buten-2-ol afforded 12 directly.

  2,4,6-三羟基二苯甲酮与2-甲基-3-丁烯-2-醇在（C2H5）2O·BF3存在下进行苄基化反应，生成2,4,6-三羟基-3,5-二苄基二苯甲酮（3）、2,6-二羟基-4-苄氧基二苯甲酮、2,6-二羟基-3-苄基-4-苄氧基二苯甲酮、苯并二吡喃和6-苯甲酰基-5,7-二羟基-2,2-二甲基-3-苄基苯并二氢吡喃。3与2摩尔对甲苯磺酰氯反应，然后甲基化和脱甲酰化，生成天然存在的二苯甲酮，即维西米阿苯甲酮A（12）。6-羟基-3,5-二苄基-2,4-二甲酰氧基二苯甲酮的环脱氢反应生成8-苯甲酰基-2,2-二甲基-6-苄基-5,7-二甲酰氧基-2H-1-苯并吡喃，脱甲酰
• Rapid Access to Polyprenylated Phloroglucinols via Alkylative Dearomatization−Annulation:  Total Synthesis of (±)-Clusianone
  作者：Ji Qi、John A. Porco

  DOI：10.1021/ja0762339

  日期：2007.10.1

  A concise approach to the bicyclo[3.3.1]nonane framework of the polyprenylated phloroglucinol natural products utilizing a tandem alkylative dearomatization-annulation sequence is described. Syntheses of (+/-)-clusianone and a complex adamantane framework have been achieved using the developed methodology.
• Cann, Martin R.; Davis, Anne-Marie; Shannon, Patrick V. R., Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1413 - 1421
  作者：Cann, Martin R.、Davis, Anne-Marie、Shannon, Patrick V. R.

  DOI：——

  日期：——