3-硝基萘-2-醇 | 32361-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-硝基萘-2-醇
• 英文名称: 3-nitro-naphthalen-2-ol
• 英文别名: 3-nitro-2-naphthol；3-Nitro-[2]naphthol；3-Nitro-naphthol-(2)；3-Nitro-2-naphtol；2-Hydroxy-3-nitronaphthalene；3-nitronaphthalen-2-ol
• CAS: 32361-60-7
• 化学式: C₁₀H₇NO₃
• 分子量: 189.17
• InChiKey: MUELWRJOJXBHPA-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  336.7±15.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2908999090

反应信息

• 作为反应物：
  描述：

  3-硝基萘-2-醇 在 四氢呋喃 、 镍 作用下， 生成 3-甲氧基萘醛
  参考文献：
  名称：

  Woodcock; Clifford, Journal of the Chemical Society, 1957, p. 4139

  摘要：

  DOI：
• 作为产物：
  描述：

  3-nitro-2-naphthyl acetate 在 a cyclophane hydrolysis 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 3-硝基萘-2-醇
  参考文献：
  名称：

  催化环烷VII。双咪唑基-环烷的酯酶活性

  摘要：

  我们报告了具有两个咪唑残基的新型四氧杂[6.1.6.1]对环环烷3的合成，该残基连接到形成大环腔的两个二苯甲烷间隔基之一的苯环上。四个乙酸残基与两个间隔单元的中心碳原子分开，并确保3在水和二元水性溶剂混合物中的溶解度。环戊烷3在含水磷酸盐缓冲液（pH 8）中与乙酸硝基萘酯形成化学计量的包合物，并在周转条件下催化结合的底物的水解。

  DOI：

  10.1002/recl.19931120605

文献信息

• Pyrrole azocrown ethers—synthesis, crystal structures, and fluorescence properties
  作者：Ewa Wagner-Wysiecka、Tomasz Rzymowski、Marina S. Fonari、Rafał Kulmaczewski、Elżbieta Luboch

  DOI：10.1016/j.tet.2011.01.027

  日期：2011.3

  Pyrrole containing macrocycles with chromophoric and fluorescent residues were prepared. X-ray structures for compounds 1 and 4 were determined. The presented pyrrole azocrowns are lead(II) chemosensors, which can be used both in UV–vis and fluorescence spectroscopy.

  制备了带有吡咯并带有发色和荧光残基的大环。确定了化合物1和4的X射线结构。提出的吡咯偶氮皇冠是铅（II）化学传感器，可用于紫外可见光谱和荧光光谱中。
• Heterocoupling of 2-naphthols enabled by a copper–N-heterocyclic carbene complex
  作者：Michael Holtz-Mulholland、Mylène de Léséleuc、Shawn K. Collins

  DOI：10.1039/c3cc38675a

  日期：——

  The reactivity of a Cu catalyst for oxidative coupling is modulated by a small molecule additive, diethyl malonate, that slows over-oxidation of 2-naphthols. Efficient heterocoupling between electron-rich and electron-poor 2-naphthols/2-naphthylamines affords C1-symmetric BINOLs with yields ranging from 35–98%.

  氧化偶联铜催化剂的反应活性受小分子添加剂丙二酸二乙酯的调节，丙二酸二乙酯可减缓 2-萘酚的过度氧化。富电子和贫电子 2-萘酚/2-萘胺之间的高效异质偶联生成了 C1 对称的 BINOL，产率为 35%-98%。
• Antitumor Agents. 5. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Dimethyl-5<i>H</i>-pyridophenoxazin-5-ones, Tetrahydro-5<i>H</i>-benzopyridophenoxazin-5-ones, and 5<i>H</i>-Benzopyridophenoxazin-5-ones with Potent Antiproliferative Activity
  作者：Adele Bolognese、Gaetano Correale、Michele Manfra、Antonio Lavecchia、Ettore Novellino、Stefano Pepe

  DOI：10.1021/jm050745l

  日期：2006.8.1

  New antiproliferative compounds, dimethyl-5H-pyrido[3,2-a] phenoxazin-5-ones (1-6), tetrahydro-5-Hbenzopyrido[2,3-j]phenoxazin-5-ones (7-9), and 5H-benzopyrido[3,2-a] phenoxazin-5-ones (10-12) were synthesized and evaluated against representative human neoplastic cell lines. Dimethyl derivatives 1-6 were more active against carcinoma than leukemia cell lines. The tetrahydrobenzo derivatives 7-9 were scarcely active, whereas the corresponding benzo derivatives 10-12 showed notable cytotoxicity against a majority of the tested cell lines. Molecular modeling studies indicated that the high potency of 10 and 11, the most cytotoxic compounds of the whole series, could be due to the position of the condensed benzene ring, which favors d-d stacking interactions with purine and pyrimidine bases in the DNA active site. Biological studies suggested that 10-12 have no effect on human topoisomerases I and II and that they induce arrest at the G2/M phase.
• Benzoxazinones as PPARγ agonists. part 1: SAR of three aromatic regions
  作者：Philip J. Rybczynski、Roxanne E. Zeck、Donald W. Combs、Ignatius Turchi、Thomas P. Burris、Jun Z. Xu、Maria Yang、Keith T. Demarest

  DOI：10.1016/s0960-894x(03)00401-3

  日期：2003.7

  A series of benzoxazinones was synthesized as PPARgamma agonists. The compounds were obtained in seven steps, and SAR was developed by variations to the core shown below. The compounds were tested as functional agonists in the induction of the aP2 gene in preadipocytes, and the most potent compound in the series has an EC50=0.51 muM. The potency was further confirmed through a PPAR-Ga14 construct. Efficacy has been demonstrated in the db/db mouse model of hyperglycemia. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Catalytic cyclophanes VII. Esterase activity of a bisimidazolyl-cyclophane
  作者：Ito Chao、François Diederich

  DOI：10.1002/recl.19931120605

  日期：——

  that shape the macrocyclic cavity. Four acetic acid residues diverge from the central carbon atoms of the two spacer units and ensure solubility of 3 in water and binary aqueous solvent mixtures. Cyclophane 3 forms stoichiometric inclusion complexes with nitronaphthyl acetates in aqueous phosphate buffers (pH 8) and catalyzes the hydrolysis of bound substrates under turnover conditions.

  我们报告了具有两个咪唑残基的新型四氧杂[6.1.6.1]对环环烷3的合成，该残基连接到形成大环腔的两个二苯甲烷间隔基之一的苯环上。四个乙酸残基与两个间隔单元的中心碳原子分开，并确保3在水和二元水性溶剂混合物中的溶解度。环戊烷3在含水磷酸盐缓冲液（pH 8）中与乙酸硝基萘酯形成化学计量的包合物，并在周转条件下催化结合的底物的水解。