N-(5-羟基萘-1-基)苯甲酰胺 | 75528-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-(5-羟基萘-1-基)苯甲酰胺
• 英文名称: 5-benzoyl-amino-1-hydroxy-naphthalene
• 英文别名: N-(5-hydroxynaphthalen-1-yl)benzamide；1-Benzoylamino-5-hydroxynaphthalin；5-benzoylamino-1-naphthol；N-(5-hydroxy-[1]naphthyl)-benzamide；N-(5-Hydroxy-[1]naphthyl)-benzamid；5-Benzoylamino-[1]naphthol
• CAS: 75528-55-1
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: HKDCEJXTXUQIQR-UHFFFAOYSA-N

物化性质

• 熔点：
  284 °C (decomp)
• 沸点：
  399.4±15.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-羟基萘-1-基)苯甲酰胺 在 ester of polyphosphoric acid 作用下， 反应 0.33h， 以13%的产率得到Benzoesaeure-(2-phenylbenzindol-5-ylester)
  参考文献：
  名称：

  Neidlein, Richard; Moller, Franz, Liebigs Annalen der Chemie, 1980, # 6, p. 971 - 979

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氨基-5-萘酚 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 48.0h， 生成 N-(5-羟基萘-1-基)苯甲酰胺
  参考文献：
  名称：

  Discovery of Potent and Selective Sirtuin 2 (SIRT2) Inhibitors Using a Fragment-Based Approach

  摘要：

  Sirtuin 2 (SIRT2) is one of the sirtuins, a family of NAD(+)-dependent deacetylases that act on a variety of histone and non-histone substrates. Accumulating biological functions and potential therapeutic applications have drawn interest in the discovery and development of SIRT2 inhibitors. Herein we report our discovery of novel SIRT2 inhibitors using a fragment-based approach. Inspired by the purported close binding proximity of suramin and nicotinamide, we prepared two sets of fragments, namely, the naphthylamide sulfonic acids and the naphthalene-benzamides and -nicotinamides. Biochemical evaluation of these two series provided structure-activity relationship (SAR) information, which led to the design of (5-benzamidonaphthalen-1/2-yloxy)nicotinamide derivatives. Among these inhibitors, one compound exhibited high anti-SIRT2 activity (48 nM) and excellent selectivity for SIRT2 over SIRT1 and SIRT3. In vitro, it also increased the acetylation level of a-tubulin, a well-established SIRT2 substrate, in both concentration- and time-dependent manners. Further kinetic studies revealed that this compound behaves as a competitive inhibitor against the peptide substrate and most likely as a noncompetitive inhibitor against NAD(+). Taken together, these results indicate that we have discovered a potent and selective SIRT2 inhibitor whose novel structure merits further exploration.

  DOI：

  10.1021/jm500777s

文献信息

• 一种利用光催化氧化萘酚类化合物合成萘醌 类化合物的方法
  申请人：中国科学院理化技术研究所

  公开号：CN106146277B

  公开（公告）日：2019-02-15

  本发明公开一种利用光催化氧化萘酚类化合物合成萘醌类化合物的方法，包括如下步骤：将萘酚类化合物溶解于异丙醇与水的混合溶液中得到反应液，将反应液移至光化学反应器，持续向光化学反应容器中通入氧气，用波长为450nm的LED单色光源照射反应液并持续搅拌进行反应，即可得到产物萘醌类化合物。本发明采用发光波长为450nm的单色LED光源代替普通光氧化过程的高压汞灯光源，利用所使用的单色LED光源和产物萘醌类化合物的吸收光谱有较好重叠的特性，无需另加光敏剂，就可以令光氧化过程自发进行并可以得到90％的产率，既大大节省了反应的成本，又减少了副反应的生成，使得产物易于分离纯化，极具商业价值。
• Green photochemistry: the use of microemulsions as green media in photooxygenation reactions
  作者：Emma E. Coyle、Kieran Joyce、Kieran Nolan、Michael Oelgemöller

  DOI：10.1039/c004869k

  日期：——

  The use of ‘green’ microemulsions of ethyl acetate and water, using sodium dodecyl sulfate and alcoholic co-surfactants as a reaction medium, in photooxygenation reactions was investigated. This work looked at the optimisation of the microemulsion (the optimum ratio of components), an investigation of the effect of changing co-surfactant and optimisation of the reaction work-up for the synthesis of 5-hydroxy-1,4-naphthoquinone, Juglone. Isolated yields of 36–88% were achieved in just 4 h of irradiation. Microemulsions also allowed the usage of the sensitiser tetraphenylporphyrin (TPP) in a benign environment. The optimised procedure was furthermore applied to the synthesis of 5-amido-1,4-naphthoquinones, and moderate yields were achieved.

  研究了在光氧化反应中使用十二烷基硫酸钠和醇类助表面活性剂作为反应介质的乙酸乙酯和水的 "绿色 "微乳液。这项研究考察了微乳液的优化（成分的最佳比例）、改变助表面活性剂的影响以及合成 5-羟基-1,4-萘醌 Juglone 的反应工作的优化。在短短 4 小时的辐照时间内，分离产率达到了 36-88%。微乳剂还允许在良性环境中使用敏化剂四苯基卟啉（TPP）。优化后的程序还被进一步应用于合成 5-氨基-1,4-萘醌，并获得了中等产量。
• Green photochemistry: solarchemical synthesis of 5-amido-1,4-naphthoquinones
  作者：Elodie Haggiage、Emma E. Coyle、Kieran Joyce、Michael Oelgemöller

  DOI：10.1039/b816676e

  日期：——

  Dye sensitized photooxygenations of 5-amido-1-naphthols were investigated with artificial light and sunlight, and the corresponding 5-amido-1,4-naphthoquinones were isolated in moderate to excellent yields. Under sunny conditions the yields were higher for almost all cases studied. The energy demand of the equipment used was determined, revealing significant energy savings for solar exposures.

  用人造光和太阳光研究了 5-酰胺基-1-萘酚的染料敏化光氧化作用，并以中等至优异的产率分离出相应的 5-酰胺基-1,4-萘醌。在阳光充足的条件下，几乎所有研究案例的产量都较高。确定了所用设备的能源需求，表明暴露在阳光下可显着节省能源。
• Separation of Mixtures with Triethylamine—Sulfur Trioxide
  作者：William B. Hardy、Mario Scalera

  DOI：10.1021/ja01140a508

  日期：1952.10
• NEIDLEIN R.; MOLLER F., LIEBIGS ANN. CHEM., 1980, NO 6, 971-979
  作者：NEIDLEIN R.、 MOLLER F.

  DOI：——

  日期：——