1,2,3,4-tetrahydrobenzo[d]naphtho[2,3-b]furan-6,11-dione | 214541-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1,2,3,4-tetrahydrobenzo[d]naphtho[2,3-b]furan-6,11-dione
• 英文别名: 1,2,3,4-Tetrahydronaphtho[3,2-b][1]benzofuran-6,11-dione
• CAS: 214541-42-1
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: QKZIROBVQPUAGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  466.1±45.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydrobenzo[d]naphtho[2,3-b]furan-6,11-dione 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 5.0h， 以42%的产率得到benzo[b]naphtho[2,3-d]furan-6,11-dione
  参考文献：
  名称：

  通过硝酸铈 (IV) 铵介导的 1,3-二羰基化合物与乙烯基硫化物的氧化环加成高效合成具有硫化物基团的二氢呋喃。在苯并[b]萘并[2,3-d]呋喃-6,11-二酮的合成中的应用及首次全合成小米花萼C和黄甲酚甲醚

  摘要：

  Ceric(IV) 硝酸铵介导的 1,3-二羰基与乙烯基硫化物的氧化环加成反应以中等收率提供了具有硫化物基团的取代二氢呋喃。这种新的合成方法已应用于苯并[b]萘并[2,3-d]呋喃-6,11-二酮和呋喃黄酮类天然产物如小米花萼素C、凤梨甲醚的合成。

  DOI：

  10.1055/s-2003-41023
• 作为产物：
  描述：

  1-(phenylthio)cyclohex-1-ene 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 xylene 为溶剂， 反应 35.0h， 生成 1,2,3,4-tetrahydrobenzo[d]naphtho[2,3-b]furan-6,11-dione
  参考文献：
  名称：

  通过硝酸铈 (IV) 铵介导的 1,3-二羰基化合物与乙烯基硫化物的氧化环加成高效合成具有硫化物基团的二氢呋喃。在苯并[b]萘并[2,3-d]呋喃-6,11-二酮的合成中的应用及首次全合成小米花萼C和黄甲酚甲醚

  摘要：

  Ceric(IV) 硝酸铵介导的 1,3-二羰基与乙烯基硫化物的氧化环加成反应以中等收率提供了具有硫化物基团的取代二氢呋喃。这种新的合成方法已应用于苯并[b]萘并[2,3-d]呋喃-6,11-二酮和呋喃黄酮类天然产物如小米花萼素C、凤梨甲醚的合成。

  DOI：

  10.1055/s-2003-41023

文献信息

• Tandem Synthesis of Furanaphthoquinones via Enamines and Evaluation of Their Antiparasitic Effects against Trypanosoma cruzi
  作者：Mariana Cardoso、Luana Forezi、Acácio de Souza、Ana Faria、Raissa Galvão、Murilo Bello、Fernando da Silva、Robson Faria、Vitor Ferreira

  DOI：10.21577/0103-5053.20210142

  日期：——

  Furanaphthoquinones are well known in medicinal chemistry for exhibiting relevant structural heterogeneity and bioactivities. In this work, it was synthesized a series of furanaphthoquinones through a tandem reaction between lawsone (8) and cyclic ketones in the presence of morpholine. This strategy provides an efficient and general method for synthesizing furanaphthoquinones with activity against the epimastigote form of Trypanosoma cruzi (T. cruzi), the parasite that causes Chagas disease. Compound 9b was the better prototype, and it exhibited high potency for causing parasite death, showed reduced acute toxicity towards mammalian cells, and was capable of rupturing the epimastigote plasma membrane and acting on sterol 14α-demethylase (CYP51). Additionally, 9b reduced trypomastigote viability by 99% after 24 h. Candidate 9b demonstrated the best and most promising profile when bound to CYP51.

  呋喃萘醌在药物化学中以其结构异质性和生物活性而闻名。本研究通过在吗啡催化下，将罗孚酮（8）和环状酮串联反应合成了一系列呋喃萘醌。该策略为合成对克氏锥虫表皮螺旋体形式（T. cruzi）具有活性的呋喃萘醌提供了一种高效而通用的方法，该寄生虫会导致查加斯病。化合物9b是更好的原型，它表现出高效的寄生虫死亡作用，对哺乳动物细胞的急性毒性减少，并能够破坏表皮螺旋体细胞膜并作用于甾体14α-去甲基酶（CYP51）。此外，9b在24小时内将试螺旋体细胞的活力降低了99%。候选物9b在与CYP51结合时表现出最佳和最有前途的特征。
• The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones
  作者：Suyou Liu、Lijun Long、Duoduo Xie、Lijun Liu、Dayou Ma

  DOI：10.1016/j.tetlet.2015.10.058

  日期：2015.12

  Naphthofuroquinones are of great value in medicinal chemistry. In this letter, a facile method for highly regioselective synthesis of both linear and angular naphthofuroquinones has been developed via iodine mediated cyclization of 2-hydroxy-3-substitutedvinyl-1,4-naphthoquinones under very mild conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• A Direct One-Pot Preparation of Naphtho[2,3-b]furan-4,9-diones from 2-Hydroxy-1,4-naphthoquinones and Enamines
  作者：Kazuhiro Kobayashi、Koujirou Tanaka、Tomokazu Uneda、Kouji Maeda、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1055/s-1998-6085

  日期：1998.9
• Efficient Synthesis of Dihydrofurans with Sulfide Groups by Ceric(IV) Ammonium Nitrate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Vinyl Sulfides. Application to the Synthesis of Benzo[<i>b</i>]naphtho[2,3-<i>d</i>]furan-6,11-dione and First Total Synthesis of Millettocalyxins C and Pongamol Methyl Ether
  作者：Yong Rok Lee、Keon Yong Kang、Gun Joon Lee、Won Kyong Lee

  DOI：10.1055/s-2003-41023

  日期：——

  Ceric(IV) ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to vinyl sulfides afforded substituted dihydrofurans with sulfide groups in moderate yields. This new synthetic method has been applied to thesynthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione and furanoflavone natural products such as millettocalyxins C and pongol methyl ether.

  Ceric(IV) 硝酸铵介导的 1,3-二羰基与乙烯基硫化物的氧化环加成反应以中等收率提供了具有硫化物基团的取代二氢呋喃。这种新的合成方法已应用于苯并[b]萘并[2,3-d]呋喃-6,11-二酮和呋喃黄酮类天然产物如小米花萼素C、凤梨甲醚的合成。
• A Facile Method for the Synthesis of Dihydrofuranonaphthoquinones, Furanonaphthoquinones, and Benzofuranonaphthoquinones
  作者：Yong Rok Lee、Byung So Kim

  DOI：10.1081/scc-120026354

  日期：2003.12.1

  An efficient synthesis of dihydrofuranonaphthoquinone, furanonaphthoquinone, and benzonaphthoquinone derivatives has been carried out starting from 2-hydroxy-1,4-naphthoquinone and a variety of vinyl sulfides in moderate yields.