2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dienone | 79740-05-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: 2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dienone
• 英文别名: 2,5-Cyclohexadien-1-one, 2-acetyl-3,5-dihydroxy-4,4,6-trimethyl-；2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dien-1-one
• CAS: 79740-05-9
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: FNQHCLOXMUUTGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dienone 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 4-Cyclohexene-1,3-dione,2-[(2E)-1-hydroxy-3-phenyl-2-propenylidene]-5-methoxy-4,6,6-trimethyl-,(2E)-
  参考文献：
  名称：

  First Total Synthesis of Desmosdumotin C^†

  摘要：

  Desmosdumotin C (1), a novel compound isolated from the roots of Desmos dumosus, was synthesized from 2,4,6-trihydroxyacetophenone (2), confirming the assigned structure of the natural product.

  DOI：

  10.1081/scc-200063907
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 、 碘甲烷 在 sodium methylate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以56%的产率得到2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dienone
  参考文献：
  名称：

  Desmosdumotins, the Method for Preparing the Same and Use as Anti-Tumor or Anti-AIDS Agents

  摘要：

  本发明揭示了制备desmosdumotin C的方法、desmosdumotin C衍生物系列及其制备方法，以及desmosdumotin B的全合成方法。本发明还揭示了衍生物的用途和含有它们的制药组合物，用于制备治疗肿瘤或艾滋病的药物。

  公开号：

  US20090233998A1

文献信息

• Biomimetic Synthesis of an Antiviral Cinnamoylphloroglucinol Collection from <i>Cleistocalyx operculatus</i>: A Synthetic Strategy Based on Biogenetic Building Blocks
  作者：Jie Wang、Jian‐Guo Song、Dong‐Lin Zhong、Zhi‐Zhang Duan、Zi‐Jian Peng、Wei Tang、Qiao‐Yun Song、Xiao‐Jun Huang、Li‐Jun Hu、Ying Wang、Wen‐Cai Ye

  DOI：10.1002/anie.202312568

  日期：2023.12.11

  Four novel cinnamoylphloroglucinol dimers were discovered from C. operculatus. Biomimetic syntheses of these and two known dimers were developed through a strategy in which the activation of stable biogenetic building blocks was a crucial step and key features included a unique cascade reaction and a rare inverse-electron-demand Diels–Alder reaction. One of the dimers showed activity against herpes simplex

  从C. operculatus中发现了四种新型肉桂酰间苯三酚二聚体。这些和两个已知二聚体的仿生合成是通过一种策略开发的，其中稳定的生物遗传构件的激活是关键步骤，关键特征包括独特的级联反应和罕见的逆电子需求狄尔斯-阿尔德反应。其中一个二聚体通过一种新的作用模式表现出对抗 1 型单纯疱疹病毒的活性。
• Synthesis and biological evaluation of cleistocaltone A, an inhibitor of respiratory syncytial virus (RSV)
  作者：Lorenz Wiese、Sophie M. Kolbe、Manuela Weber、Martin Ludlow、Mathias Christmann

  DOI：10.1039/d4sc01897d

  日期：——

  reported to show promising antiviral properties. Based on a modified biosynthesis proposal, a synthetic strategy was devised featuring an intramolecular Diels–Alder reaction and an epoxidation/elimination sequence to generate the allyl alcohol handle in the side chain. The strategy was successfully executed and synthetic cleistcaltone A was evaluated against a contemporary RSV-A strain.

  首次化学合成间苯三酚间萜类闭锁内酯 A ( 1 )。据报道，这种化合物先前从Cleistocalyx operculatus中分离出来，具有良好的抗病毒特性。基于改进的生物合成方案，设计了一种合成策略，其特征是分子内狄尔斯-阿尔德反应和环氧化/消除序列，以在侧链中生成烯丙醇手柄。该策略成功执行，并针对当代 RSV-A 菌株对合成的 cleistcaltone A 进行了评估。
• Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone
  作者：Ngoc Tuan Nguyen、Van Cuong Pham、Marc Litaudon、Françoise Guéritte、Bernard Bodo、Van Tuyen Nguyen、Van Hung Nguyen

  DOI：10.1016/j.tet.2009.06.017

  日期：2009.8

  Two new compounds, a cyclic peptide desmocyclopeptide (1) and a special flavone desmorostratone (2) were isolated from the stem bark of Desmos rostrata, along with two known compounds, desmosdumotins B (3) and C (4). Their Structures were established on the basis of the spectral data, including mass spectrometry and 2D NMR. The total synthesis of desmorostratone (2) was performed in order to confirm its structure as well as that of desmosdumotin C (4), which was a tautomeric mixture in the solution. Finally, cytotoxity of these compounds were evaluated. Desmosdumotin C (4) displayed a moderate inhibition activity against KB cell line with an IC50 of 19.2 mu M, whereas the other products showed a weak inhibition against the same cell line target. (c) 2009 Elsevier Ltd. All rights reserved.
• Balwe,T. et al., Chemische Berichte, 1966, vol. 99, p. 3277 - 3287
  作者：Balwe,T. et al.

  DOI：——

  日期：——
• Frutescone A–G, Tasmanone-Based Meroterpenoids from the aerial parts of <i>Baeckea frutescens</i>
  作者：Ji-Qin Hou、Cui Guo、Jian-Juan Zhao、Qi-Wei He、Bao-Bao Zhang、Hao Wang

  DOI：10.1021/acs.joc.6b02643

  日期：2017.2.3

  Frutescone A-G [(1-6), (+)-7, (-)-7], a new group of naturally occurring tasmanone-based meroterpenoids, were isolated from the aerial parts of Baeckea frutescens L. Compounds 1 and 4 featured a rare carbon skeleton with an unprecedented oxa-spiro[5.8] tetradecadiene ring system, existing as two favored equilibrating conformers in CDCl3 solution, identified by variable-temperature NMR. The regioselective syntheses of 4-7 were achieved in a concise manner by a biomimetically inspired key hetero-Diels Alder reaction "on water". Compounds 1, 4, and 5 exhibited moderate cytotoxicities in vitro.