5-ethoxy-1,4-naphthoquinone | 22924-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-ethoxy-1,4-naphthoquinone
• 英文别名: 1,4-Naphthoquinone, 5-ethoxy-；5-ethoxynaphthalene-1,4-dione
• CAS: 22924-19-2
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: AFUYDNZGZMWKER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5-ethoxy-1,4-naphthoquinone 、 苊烯 在 6[Pd(en)(NO₃)2]*4[2,4,6-tri(4-pyridyl)-1,3,5-triazine] 作用下， 以 重水 为溶剂， 反应 3.0h， 以86%的产率得到(2S,3S,12R,13R)-6-ethoxyhexacyclo[12.7.1.02,13.03,12.05,10.018,22]docosa-1(21),5(10),6,8,14,16,18(22),19-octaene-4,11-dione
  参考文献：
  名称：

  自组装配位笼内的空腔定向合成：烯烃的高选择性 [2 + 2] 交叉光二聚化

  摘要：

  本文报道了烯烃在自组装配位笼内的高选择性 [2 + 2] 交叉光二聚化，该配位笼在水性介质中充当分子烧瓶。从六个 Pd(II) 配合物和四个三齿配体自组装的 M(6)L(4) 配位纳米笼以成对的选择性方式容纳两种不同类型的大烯烃分子，如苊和 5-乙氧基萘醌。这种先决条件识别模式使得空腔内烯烃的选择性[2+2]交叉光二聚化成为可能。该反应在反应速率、立体选择性以及最重要的成对选择性方面非常有效。马来酰亚胺衍生物，其本身在普通条件下是无光化学活性的，还可以非常有效地与苊或二苯并丁二烯交叉二聚。这些结果与有机介质中常见的光二聚反应形成鲜明对比，后者的产率和选择性通常较差至中等。交叉二聚体排他性形成的关键步骤源于辐照前三元复合物的选择性形成，这取决于客体与腔体密闭空间的大小相容性。

  DOI：

  10.1021/ja020718+
• 作为产物：
  描述：

  1,5-二羟基萘 在 双氧水 、 乙酸酐 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 5-ethoxy-1,4-naphthoquinone
  参考文献：
  名称：

  通过可见光介导醌与 α-酮酸的氢酰化合成酰基氢醌

  摘要：

  已经开发出一种温和且环保的可见光诱导醌与 α-酮酸的氢酰化方案。在没有任何催化剂或添加剂的情况下，脱羧加氢酰化反应在室温可见光照射下顺利进行。多种醌和 α-酮酸具有良好的耐受性，并提供高达 88% 的分离产率的加氢酰化产物。该反应可以扩大规模，并且诱导的基团可用于进一步的合成应用。初步的机理研究表明，光敏醌吸收可见光以促进转化。

  DOI：

  10.1021/acs.joc.3c02361

文献信息

• Solar photochemistry: optimisation of the photo Friedel–Crafts acylation of naphthoquinones
  作者：Lorna J. Mitchell、William Lewis、Christopher J. Moody

  DOI：10.1039/c3gc41477a

  日期：——

  A practical and robust photo Friedel–Crafts acylation of naphthoquinones is described. Although the reaction proceeds slowly in sunlight, the optimised conditions offer a substantial improvement to those already reported, by the utilisation of a more reliable and practical ‘sun-mimicking’ light source, a less hazardous solvent system (trifluorotoluene) and faster reaction times. Using these conditions, the reaction scope has been expanded to include functionalised aldehyde and naphthoquinone substrates, affording the desired photo-products in acceptable to excellent yields (17–81%). Factors influencing the regiochemistry of the photo Friedel–Crafts reaction on unsymmetrical naphthoquinones have also been investigated.

  本文介绍了一种实用而可靠的萘醌光弗里德酰化反应。虽然该反应在阳光下进行得很慢，但优化后的条件与已报道的条件相比有了很大改进，因为它利用了更可靠、更实用的 "模拟太阳 "光源、危害更小的溶剂系统（三氟甲苯）以及更快的反应时间。利用这些条件，反应范围扩大到包括官能化醛和萘醌底物，以可接受到极好的收率（17%-81%）获得所需的光反应产物。此外，还研究了影响不对称萘醌的光弗里德卡夫斯反应的区域化学性质的因素。
• Light-Driven Carbon–Carbon Coupling of α-sp³–CH of Aliphatic Alcohols with sp²–CH Bond of 1,4-Naphthoquinones
  作者：Raushan Kumar Jha、Aditya Upadhyay、Kanika、Saket Jain、Neena K A、Sangit Kumar

  DOI：10.1021/acs.orglett.2c03066

  日期：2022.10.21

  Here, an α-selective Csp3–H bond functionalization of primary aliphatic alcohols with 1,4-naphthoquinones yielded Csp2–Csp2 coupled products driven by blue-LED light under catalyst, metal, base, and reagent-free conditions. In this transformation, cleavage of three C–H bonds (two sp3–C-H, one sp2–C–H, and one O–H) and four new bonds formed, leading to fluorescent 2-acylated-1,4-naphthohydroquinones

  在这里，在催化剂、金属、碱和无试剂条件下，脂肪伯醇与 1,4-萘醌的 α-选择性 C sp3 -H 键官能化产生了由蓝色 LED 光驱动的 C sp 2 -C sp 2偶联产物. 在该转化过程中，三个 C-H 键（两个 sp 3 -CH、一个 sp 2 -C-H 和一个 O-H）断裂并形成四个新键，从而产生荧光 2-acylated-1,4-naphthohydroquinones .
• 2-Propargylamino-naphthoquinone derivatives as multipotent agents for the treatment of Alzheimer’s disease
  作者：Eva Mezeiova、Jana Janockova、Rudolf Andrys、Ondrej Soukup、Tereza Kobrlova、Lubica Muckova、Jaroslav Pejchal、Miriama Simunkova、Jiri Handl、Petra Micankova、Jan Capek、Tomas Rousar、Martina Hrabinova、Eugenie Nepovimova、Jose Luis Marco-Contelles、Marian Valko、Jan Korabecny

  DOI：10.1016/j.ejmech.2020.113112

  日期：2021.2
• Novel juglone and plumbagin 5- O derivatives and their in vitro growth inhibitory activity against apoptosis-resistant cancer cells
  作者：Serena Fiorito、Salvatore Genovese、Vito Alessandro Taddeo、Véronique Mathieu、Robert Kiss、Francesco Epifano

  DOI：10.1016/j.bmcl.2015.12.017

  日期：2016.1

  Juglone 1 an plumbagin 2 are plant secondary metabolites nowadays well known for their anticancer properties. In this study we synthesized analogues of 1 and 2 deriving from the functionalization of the OH group in position 5 with different side chains in form of esters and ethers. Therefore the growth inhibitory activities of these adducts were evaluated in vitro on six cancer cell lines using the MTT colorimetric assays along with the two natural parent compounds. The data revealed that these latter displayed the strongest growth inhibitory activities in vitro. Quantitative videomicroscopy analyses were then carried out on human U373 glioblastoma cells, which are characterized by various level of resistance to pro-apoptotic stimuli. We compared the naturally occurring reference compounds 1 and 2 with the derivatives exerting the best activities in terms of IC50 growth inhibitory values. These analyses showed that both juglone and plumbagin had a cytostatic effect on U373 cells and were able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli. (C) 2015 Elsevier Ltd. All rights reserved.
• COMPOUND, POLYMERIZABLE COMPOSITION, CURED PRODUCT, OPTICAL FILM, POLARIZING PLATE, AND IMAGE DISPLAY DEVICE
  申请人：FUJIFILM Corporation

  公开号：US20220011488A1

  公开（公告）日：2022-01-13

  Provided is a compound having a wide temperature range exhibiting liquid crystallinity and excellent precipitation suppression and solubility; and a polymerizable composition, a cured product, an optical film, a polarizing plate, and an image display device, each using the compound. The compound is represented, for example, by Formula (1) or (2).