2-hydroxy-3-(3-oxo-3-phenylpropyl)-1,4-naphthalenedione | 1035092-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3-(3-oxo-3-phenylpropyl)-1,4-naphthalenedione
• 英文别名: 2-hydroxy-3-(3-oxo-3-phenylpropyl)naphthalene-1,4-dione
• CAS: 1035092-57-9
• 化学式: C₁₉H₁₄O₄
• 分子量: 306.318
• InChiKey: WIUQKOHOTLRZDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  71.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯甲酸甲酯 在 dipotassium peroxodisulfate 、 titanium(IV)isopropoxide 、 silver nitrate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 2-hydroxy-3-(3-oxo-3-phenylpropyl)-1,4-naphthalenedione
  参考文献：
  名称：

  γ-Carbonyl Quinones: Radical Strategy for the Synthesis of Evelynin and Its Analogues by C–H Activation of Quinones Using Cyclopropanols

  摘要：

  Cyclopropanols, on oxidative ring opening with AgNO3-K2S2O8 in DCM-H2O at room temperature and under open flask conditions, produced beta-keto radicals which were successfully added to quinones to furnish gamma-carbonyl quinones. This mild method has been applied to the synthesis of cytotoxic natural products, 4,6-dimethoxy-2,5-quinodihydrochalcone and evelynin.

  DOI：

  10.1021/ol402229m

文献信息

• Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis
  作者：Benito Alcaide、Pedro Almendros、M. Teresa Quirós、Ramón López、María I. Menéndez、Aleksandra Sochacka-Ćwikła

  DOI：10.1021/ja3108966

  日期：2013.1.16

  Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ketones. Moreover, the utility of some of the resulting products for the selective preparation of fused polycycles has been demonstrated. In addition

  伯和仲炔丙基氢过氧化物与各种亲核试剂（包括醇、酚、2-羟基萘-1,4-二酮和吲哚）的受控金催化反应允许直接有效地合成 β-官能化酮。此外，已经证明了一些所得产物用于选择性制备稠合多环的效用。此外，还进行了密度泛函理论 (DFT) 计算和 (18) O 标记实验，以深入了解炔丙基氢过氧化物与外部亲核试剂在金催化下的受控反应性的各个方面。
• Synthesis of Siloxy-α-Lapachone Derivatives by Chemo- and Regioselective Diels-Alder Reactions of 3-Methylene-1,2,4-naphthotriones with Silyl Enol Ethers
  作者：Jian-Hua Xu、Da-Quan Peng、Yun Liu、Zhi-Feng Lu、Yong-Miao Shen

  DOI：10.1055/s-2008-1042950

  日期：2008.4

  2-hydroxy-1,4-naphthoquinone with aliphatic and aromatic aldehydes, take part in chemoselective hetero-Diels-Alder reactions with silyl enol ethers to give a series of siloxy-containing naphtho[2,3- B]pyran-5,10-dione (α-lapachone) derivatives in moderate to high yield. These reactions regio-selectively gave α-lapachone derivatives with an acetal structure. This regioselectivity can be rationalized by

  O-醌甲基化物，由 2-羟基-1,4-萘醌与脂肪族和芳香族醛的 Knoevenagel 缩合原位生成，与甲硅烷基烯醇醚参与化学选择性杂-Diels-Alder 反应，得到一系列含甲硅烷氧基的化合物萘并[2,3- B]吡喃-5,10-二酮（α-拉帕酮）衍生物，产率中等至高。这些反应区域选择性地产生具有缩醛结构的α-拉帕酮衍生物。这种区域选择性可以通过考虑邻醌甲基化物与甲硅烷基烯醇醚的前沿分子轨道相互作用来合理化，并考虑到能量上更有利的途径导致迈克尔加成中低能量的两性离子状过渡态两种反应物。
• γ-Carbonyl Quinones: Radical Strategy for the Synthesis of Evelynin and Its Analogues by C–H Activation of Quinones Using Cyclopropanols
  作者：Andivelu Ilangovan、Shanmugasundar Saravanakumar、Subramani Malayappasamy

  DOI：10.1021/ol402229m

  日期：2013.10.4

  Cyclopropanols, on oxidative ring opening with AgNO3-K2S2O8 in DCM-H2O at room temperature and under open flask conditions, produced beta-keto radicals which were successfully added to quinones to furnish gamma-carbonyl quinones. This mild method has been applied to the synthesis of cytotoxic natural products, 4,6-dimethoxy-2,5-quinodihydrochalcone and evelynin.