4-hydroxy-8-methoxynaphthalene-1,2-dione | 13261-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-8-methoxynaphthalene-1,2-dione
• 英文别名: 2-hydroxy-8-methoxy-[1,4]naphthoquinone；2-hydroxy-8-methoxy-1,4-naphthoquinone；3-Hydroxy-5-methoxy-1,4-naphthoquinone；3-Hydroxy-5-methoxy-naphthochinon-(1,4)；2-Hydroxy-8-methoxy-1,4-naphthochinon；Hydroxyjuglon-methylether
• CAS: 13261-50-2
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: FYKICSYZKOGCIS-UHFFFAOYSA-N

物化性质

• 熔点：
  211-214 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  414.3±45.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-8-methoxynaphthalene-1,2-dione 在 三溴化硼 作用下， 生成 4,8-dihydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  Giles,R.G.F.; Roos,G.H.P., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1632 - 1635

  摘要：

  DOI：
• 作为产物：
  描述：

  甲氧苯醌 在 sodium hydroxide 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 2.5h， 生成 4-hydroxy-8-methoxynaphthalene-1,2-dione
  参考文献：
  名称：

  碱性条件下甲氧基-2-羟基-1,4-萘醌的合成及一种异构体与醛的反应

  摘要：

  摘要 研究了合成甲氧基-2-羟基-1,4-萘醌的两种方案，以评估它们在胺碱性条件下对醛的行为。醌和脂肪族醛的性质都有助于这种缩合的可行性以及进一步的转化。

  DOI：

  10.1081/scc-120030312

文献信息

• One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition
  作者：Kazuhiro Kobayashi、Tomokazu Uneda、Koujirou Tanaka、Masako Mori、Hideo Tanaka、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.71.1691

  日期：1998.7

  The 3+2-type cycloaddition reaction of 2-hydroxy-1,4-naphthoquinones with various alkenes or phenylacetylene was mediated by ammonium cerium(IV) nitrate (CAN) to give the corresponding naphtho[2,3-b]furan-4,9-dione and naphtho[1,2-b]furan-4,5-dione derivatives. The reaction of 2-hydroxy-1,4-benzoquinones with alkenes in the presence of CAN similarly proceeded to give benzofuran-4,7-dione and benzofuran-4,5-dione derivatives. 3-Hydroxy-1H-phenalen-1-one also underwent the CAN-mediated cycloaddition with alkenes or phenylacetylene to give the corresponding 7H-phenaleno[1,2-b]furan-7-one derivatives.

  2-羟基-1,4-萘醌与各种烯烃或苯乙炔在硝酸铈铵（CAN）的催化下发生3+2型环加成反应，生成相应的萘并[2,3-b]呋喃-4,9-二酮和萘并[1,2-b]呋喃-4,5-二酮衍生物。2-羟基-1,4-苯醌与烯烃在CAN存在下同样发生反应，得到苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物。3-羟基-1H-菲兰烯-1-酮也能在CAN的催化下与烯烃或苯乙炔发生环加成反应，生成相应的7H-菲兰诺[1,2-b]呋喃-7-酮衍生物。
• Synthesis, Characterization and Cytotoxic Investigations of Novel C3-Dihydrofuran Substituted 1H-benzo[g]chromene-2,5,10-triones besides Antimicrobial study
  作者：Venkata Swamy Tangeti、D. Vasundhara、M. Naresh Kumar、Himabindu Mylapalli、Kaja Srinivas Pavan Kumar

  DOI：10.14233/ajchem.2017.20209

  日期：——

  A series of novel C3-dihydrofuran substituted 1H-benzo[g]chromene-2,5,10-triones were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial and anticancer activities and structure and activity relationship (SAR) was investigated. Structure and activity relationship studies revealed that the compounds 6p, 6q, 6s, 6t were found to be more active in antimicrobial screening. Antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, C3-dihydrofuran substituted 1H-benzo[g]chromene-2,5,10-trione with methoxy group substitution at ring A and B were selected for further structure activity relationship. Among the derivatives, (2S,3S)-propyl-4-acetyl-5-(7,9-dimethoxy-2,5,10-trioxo-5,10-dihydro-2H-benzo[g]chromen-3-yl)-3-(3,5-dimethoxyphenyl)-2,3-dihydrofuran-2-carboxylate (6t) showed most potent cytotoxic activity against all the three cancer cell lines. Toxicity studies revealed that dihydrofuran substituted 1H-benzo[g] chromene-2,5,10-triones (6a-t) are specifically target the cancer cell lines.

  合成了一系列新型C3-二氢呋喃取代的1H-苯并[g]色烯-2,5,10-三酮，并通过光谱分析对其进行了表征。针对这些靶分子进行了抗微生物和抗癌活性的筛选，并研究了其结构与活性关系（SAR）。结构与活性关系研究显示，化合物6p、6q、6s、6t在抗微生物筛选中表现更为活跃。抗增殖特性则针对人类癌细胞系进行评估，包括喉癌（Hep2）、肺腺癌（A549）和宫颈癌（HeLa）。在这些化合物中，C3-二氢呋喃取代的1H-苯并[g]色烯-2,5,10-三酮A和B环上有甲氧基取代的化合物被选为进一步的结构活性关系研究。在这些衍生物中，(2S,3S)-丙基-4-乙酰基-5-(7,9-二甲氧基-2,5,10-三氧-5,10-二氢-2H-苯并[g]色烯-3-基)-3-(3,5-二甲氧基苯基)-2,3-二氢呋喃-2-羧酸酯（6t）对所有三种癌细胞系表现出最强的细胞毒活性。毒性研究表明，二氢呋喃取代的1H-苯并[g]色烯-2,5,10-三酮（6a-t）特异性靶向癌细胞系。
• Synthesis and Cytotoxicity on Human Leukemia Cells of Furonaphthoquinones Isolated from <i>Tabebuia</i> Plants
  作者：Ryuta Inagaki、Masayuki Ninomiya、Kaori Tanaka、Kunitomo Watanabe、Mamoru Koketsu

  DOI：10.1248/cpb.c13-00011

  日期：——

  Furonaphthoquinones are promising skeletons for anticancer drug molecules. In particular, methoxylated furonaphthoquinones are characteristic constituents of Tabebuia plants. In this research, we synthesized the furonaphthoquinones by effective one-pot cascade reactions of 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenides with 3-butyn-2-ol in the presence of palladium and cuprous catalysts via Sonogashira coupling and intramolecular cyclization. Furthermore, we demonstrated that the synthetic furonaphthoquinones showed moderate cytotoxicity against human leukemia U937 and HL-60 cells. Our work highlights the importance of furonaphthoquinones as antileukemic agents.

  呋喃萘醌类化合物是抗癌药物分子很有前途的骨架。特别是甲氧基化的呋喃萘醌类化合物是 Tabebuia 植物的特征成分。在这项研究中，我们在钯和亚铜催化剂存在下，通过 Sonogashira 偶联和分子内环化反应，以 3-苯基碘-1,2,4-三氧代-1,2,3,4-四氢萘化物和 3-丁炔-2-醇为原料，进行了有效的一锅级联反应，合成了呋喃萘醌类化合物。此外，我们还证明了合成的呋喃萘醌类化合物对人类白血病 U937 和 HL-60 细胞具有适度的细胞毒性。我们的工作凸显了呋喃并萘醌类化合物作为抗白血病药物的重要性。
• One-step preparation of some 2-isopropenyl-2,3-dihydronaphtho-[2,3-<i>b</i>]furan-4,9-diones
  作者：Seiji Yamaguchi、Toshiharu Katsuki、Hajime Yokoyama、Yoshiro Hirai

  DOI：10.1002/jhet.5570380235

  日期：2001.3

  Some 2-isopropenyl-2,3-dihydronaphtho[2,3-b]furan-4,9-diones la-f,b',f were prepared by one-step cyclizations of 2-hydroxy-1,4-naphthoquinones 2a-f with 1,4-dibromo-2-methyl-2-butene (3).

  通过2-羟基-1,4-萘醌2a的一步环化制备了一些2-异丙烯基-2,3-二氢萘[2,3- b ]呋喃-4,9-二酮la-f，b'，f。-f与1，4-二溴-2-甲基-2-丁烯（3）。
• Photochemical Reaction of 1,2-Naphthoquinone toward Enantioselective Synthesis of γ-Rubromycin: Viability Dependence on Chromophore
  作者：Yoshio Ando、Ken Ohmori、Daichi Ogawa、Fumihiro Wakita、Keisuke Suzuki

  DOI：10.1055/a-2113-0212

  日期：2024.3

  at the enantioselective total synthesis of γ-rubromycin, we reported the photochemical reaction of 1,2-naphthoquinone as a promising solution to otherwise-difficult enantiocontrol of the single spiroacetal stereogenic center. The present study examined the applicability of this approach to more functionalized substrates, which revealed viability dependence on the chromophore structure differing in the

  针对γ-红霉素的对映选择性全合成，我们报道了1,2-萘醌的光化学反应，作为解决单个螺缩醛立体中心的对映控制困难的有前景的解决方案。本研究检验了这种方法对功能化程度更高的底物的适用性，结果揭示了活力对甲氧基取代基位置和数量不同的发色团结构的依赖性。

表征谱图