2-phenyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione | 90149-96-5

• 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: 2-phenyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
• 英文别名: 2H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2-phenyl-
• CAS: 90149-96-5
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: XUGUBVAGWOTZPF-UHFFFAOYSA-N

物化性质

• 熔点：
  161-163 °C
• 沸点：
  480.8±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  2-phenyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 在 双氧水 、 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到2-phenyl-3,4-dihydroindeno[1,2-b]pyran-5(2H)-one
  参考文献：
  名称：

  A New One-Pot Procedure for a Ring Contraction Reaction using Iodine/H₂O₂

  摘要：

  报告了一种利用 H2O2 水溶液（30%）和乙腈中催化量 I2 从 1,2-quinones 缩环的新方法。

  DOI：

  10.1055/s-0028-1083519
• 作为产物：
  描述：

  2-hydroxy-3-(3-phenylallyl)-1,4-naphthoquinone 在 硫酸 作用下， 反应 0.25h， 以93%的产率得到2-phenyl-3,4-dihydro-2H-benzo[h]chromene-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

• Synthesis and Pharmacophore Modeling of Naphthoquinone Derivatives with Cytotoxic Activity in Human Promyelocytic Leukemia HL-60 Cell Line
  作者：Elisa Pérez-Sacau、Raquel G. Díaz-Peñate、Ana Estévez-Braun、Angel G. Ravelo、Jose M. García-Castellano、Leonardo Pardo、Mercedes Campillo

  DOI：10.1021/jm060849b

  日期：2007.2.1

  quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands

  催化剂/ HypoGen药效团建模方法和三维定量结构-活性关系（3D-QSAR）/比较分子相似性指数分析（CoMSIA）方法已成功用于解释一组测试的51种天然和合成萘醌衍生物的细胞毒活性在人早幼粒细胞白血病HL-60细胞系中。计算模型促进了对抗肿瘤特性至关重要的配体结构元素的鉴定。高活性β-环-吡喃-1,2-萘醌[0.1 microM
• 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。
• Hetero-Diels–Alder Reactions of Quinone Methides: The Origin of the α-Regioselectivity of 3-Methylene-1,2,4-naphthotriones
  作者：Maicon Delarmelina、Sabrina B. Ferreira、Fernando de C. da Silva、Vitor F. Ferreira、José Walkimar de M. Carneiro

  DOI：10.1021/acs.joc.0c00215

  日期：2020.6.5

  previously reported for other quinone methide intermediates are also observed for 3-methylene-1,2,4-naphthotriones, such as small endo/exo diastereoselectivity, as well as pronounced ortho/meta regioselectivity for reactions performed with dienophile containing electron-releasing groups. The results presented here provide a deeper understanding of the reactivity of quinone methide derivatives, aiding the

  通过实验和计算方法研究了通过异狄尔斯-阿尔德反应的α-和β-拉帕酮的区域选择性形成。详细探讨了实验观察到的α-选择性，发现与β-异构​​体相比，形成α-lapachone的较低能垒是整个反应路径中较低的Pauli排斥力的结果。根据活化应变模型（ASM）和能量分解分析（EDA），通过比较α-和β-拉帕酮势能面（PES）上的等效点，我们能够证明Pauli排斥项在从反应物要TS β比TS α，导致反应路径早期和β-拉帕酮的过渡态反应能降低。此外，我们证实先前针对其他醌甲基化物中间体报道，区域选择性和非对映选择性的趋势也为3-亚甲基-1,2,4- naphthotriones，如小观察到内切/外切非对映选择性，以及显着的邻位/间位与含有电子释放基团的亲二烯体进行的反应的区域选择性。此处提供的结果提供了对醌甲基化物衍生物反应性的更深入的理解，有助于未来反应条件的合理设计，可能的醌甲基化物中间体的结构
• 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。
• Synthesis of New o-Quinone Methides from β-Lapachone Analogues
  作者：Vitor Ferreira、Sabrina Ferreira、Daniel Gonzaga、Fernando de Carvalho da Silva、Katia de Lima Araújo

  DOI：10.1055/s-0030-1260778

  日期：2011.7

  In this work, we synthesized six new o-quinone methides from β-lapachone analogues by treating β-lapachone with acetone and a catalytic amount of iodine under thermal conditions and microwave irradiation. The yields of isolated o-quinone methides ranged from 20-80%. During the reactions, the formation of α-pyran naphthoquinones was observed; the yields varied depending upon the substituent. The reactions

  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。