3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[1,2-b]pyran-5,6-dione | 90149-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[1,2-b]pyran-5,6-dione
• 英文别名: 3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[1,2b]pyran-5,6-dione；2-methyl-2-phenyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione；CG 9-442；2-Methyl-2-phenyl-3,4-dihydrobenzo[h]chromene-5,6-dione
• CAS: 90149-97-6
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: NIQCRSHOBPZURY-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  476.5±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[1,2-b]pyran-5,6-dione 、 丙酮 在 碘 作用下， 反应 0.17h， 生成 3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[2,3-b]pyran-5,10-dione 、
  参考文献：
  名称：

  从 β-Lapachone 类似物合成新的邻醌甲基化物

  摘要：

  在这项工作中，我们通过在热条件和微波辐射下用丙酮和催化量的碘处理 β-拉帕酮，从 β-拉帕酮类似物合成了六种新的邻醌甲基化物。分离的邻醌甲基化物的产率范围为 20-80%。在反应过程中，观察到α-吡喃萘醌的形成；产率因取代基而异。使用微波辐射的反应速度更快，但产率和选择性没有显着变化。

  DOI：

  10.1055/s-0030-1260778
• 作为产物：
  描述：

  (E)-3-phenylbut-2-en-1-ol 在 吡啶 、 氢氧化钾 、 硫酸 、 三溴化磷 、 potassium iodide 作用下， 以 乙醚 、 Petroleum ether 为溶剂， 反应 17.25h， 生成 3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[1,2-b]pyran-5,6-dione
  参考文献：
  名称：

  .beta.-Lapachone: synthesis of derivatives and activities in tumor models

  摘要：

  In order to find a 3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative [beta-lapachone (10a)], we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring. Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity. Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a. However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as the 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.

  DOI：

  10.1021/jm00374a010

文献信息

• Trapping of Active Methylene Intermediates with Alkenes, Indoles or Thiols: Towards Highly Selective Multicomponent Reactions
  作者：Yanlong Gu、Joël Barrault、François Jérôme

  DOI：10.1002/adsc.200900593

  日期：2009.12

  In this paper, a basic method to access new multicomponent reactions (MCRs) is reported. The mechanism of these MCRs is based on the trapping of methylene intermediates, formed in situ by reaction of formaldehyde with electron-rich carbons, with alkene, thiol or indole derivatives. According to our strategy, a wide range of valuable skeletons has been obtained in a one-pot reaction, thus allowing a

  在本文中，报告了一种访问新的多组分反应（MCR）的基本方法。这些MCR的机理基于对亚甲基中间体的捕获，该中间体是通过甲醛与富含电子的碳与烯烃，硫醇或吲哚衍生物反应原位形成的。根据我们的策略，通过一锅法反应已经获得了多种有价值的骨架，因此可以最大程度地减少浪费，成本和劳动力。所提出的方法展示了广泛的底物范围，并且发现羟基或羰基的α-位的富电子碳特别有效。更广泛地讲，这项工作为从最简单的有机组成部分之一甲醛创造分子复杂性和多样性提供了新的工具。
• Site-selectivity control in hetero-Diels–Alder reactions of methylidene derivatives of lawsone through modification of the reactive carbonyl group: an experimental and theoretical study
  作者：Maria Tsanakopoulou、Erifili Tsovaltzi、Marina A. Tzani、Periklis Selevos、Elizabeth Malamidou-Xenikaki、Evangelos G. Bakalbassis、Luis R. Domingo

  DOI：10.1039/c8ob02383b

  日期：——

  an acetal derivative of lawsone was synthesized, isolated, and used in tandem Knoevenagel/hetero-Diels–Alder reactions catalyzed by S-proline. The intermediate alkylidene-1,3-diones that were formed in situ reacted with electron rich alkenes to predominantly afford pyrano-1,2-naphthoquinone (β-lapachone) derivatives along with the isomeric pyrano-1,4-naphthoquinone (α-lapachone) derivatives in high to

  合成，分离并在S-脯氨酸催化的Knoevenagel /杂Diels-Alder串联反应中使用了Lawone的缩醛衍生物，揭示了对羟基醌反应性的新观点。原位形成的中间体亚烷基-1,3-二酮与富电子烯烃反应，主要提供吡喃基1,2-萘醌（β-lapachone）衍生物以及异构体吡喃-1,4-萘醌（α-lapachone） ）以高至优异的总收益率衍生。有趣的是，发现高反应性的亚芳基-1,3-二酮衍生物是稳定且可分离的。DFT计算表明，这些杂Diels-Alder反应具有高极性，这是通过两步一步进行的机制。对概念DFT指数的分析可以解释观察到的显着位点选择性。
• Synthesis and anti-Trypanosoma cruzi activity of β-lapachone analogues
  作者：Sabrina Baptista Ferreira、Kelly Salomão、Fernando de Carvalho da Silva、Antônio Ventura Pinto、Carlos Roland Kaiser、Angelo C. Pinto、Vitor Francisco Ferreira、Solange L. de Castro

  DOI：10.1016/j.ejmech.2011.03.012

  日期：2011.7

  the effect on bloodstream trypomastigotes of 16 new naphthoquinone analogues of β-lapachone modified in the pyran ring, aiming to find a new prototype with high trypanocidal activity. The new compounds presented a broad spectrum of activity, and five of them presented IC50/24 h in the range of 22–63 μM, whereas β-lapachone had a higher value of 391.5 ± 16.5 μM.

  由克氏锥虫引起的南美锥虫病的可用化学疗法并不令人满意；因此，人们努力寻找治疗这种疾病的新药。在我们的实验室，我们分析了 16 种新型萘醌类似物在吡喃环上修饰的 β-拉帕醌对血流锥鞭毛体的影响，旨在寻找一种具有高杀锥虫活性的新原型。新化合物具有广谱活性，其中五种化合物的IC 50 /24 h 范围为22-63 μM，而β-拉帕酮的IC 50 /24 h 值更高，为391.5 ± 16.5 μM。
• PHARMACEUTICAL COMPOSITION FOR THE TREATMENT AND PREVENTION OF DISEASES INVOLVING IMPOTENCE
  申请人：Kwak Taehwan

  公开号：US20100239674A1

  公开（公告）日：2010-09-23

  Disclosed is a pharmaceutical composition for the treatment and/or prevention of erectile dysfunction, comprising (a) a therapeutically effective amount of a compound represented by Formula 1 or 2, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  本发明公开了一种用于治疗和/或预防勃起功能障碍的药物组合物，包括（a）按照式1或式2表示的化合物的治疗有效量，以及（b）药学上可接受的载体、稀释剂或赋形剂，或其任意组合。
• Pharmaceutical Composition for the Treatment or Prevention of Diseases Involving Obesity, Diabetes, Metabolic Syndrome, Neuro-Degenerative Diseases and Mitochondria Dyfunction Diseases
  申请人：Yoo Sang-Ku

  公开号：US20080146655A1

  公开（公告）日：2008-06-19

  Provided is a pharmaceutical composition for the treatment and prevention of obesity, diabetes, metabolic syndromes, degenerative diseases and mitochondrial dysfunction-related diseases, comprising: a therapeutically effective amount of a compound represented by Formula I below, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供一种药物组合物，用于治疗和预防肥胖、糖尿病、代谢综合征、退行性疾病和线粒体功能障碍相关疾病，包括：以下式I所表示的化合物的治疗有效量，或其药学上可接受的盐、前药、溶剂或异构体，以及药学上可接受的载体、稀释剂或赋形剂，或其任意组合。