2-benzoxazol-2-yl-4-nitrophenol | 60344-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-benzoxazol-2-yl-4-nitrophenol
• 英文别名: 2-(2-hydroxy-5-nitrophenyl)benzoxazole；2-(2′-hydroxy-5′-nitrophenyl)-1,3-benzoxazole；5'-Nitro-2-(2-hydroxyphenyl)benzoxazol；2-benzooxazol-2-yl-4-nitro-phenol；2-(1,3-Benzoxazol-2-yl)-4-nitrophenol
• CAS: 60344-96-9
• 化学式: C₁₃H₈N₂O₄
• 分子量: 256.218
• InChiKey: UTONFZSGJLALAA-UHFFFAOYSA-N

物化性质

• 熔点：
  188 °C(Solv: acetic acid (64-19-7))
• 沸点：
  427.3±35.0 °C(Predicted)
• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzoxazol-2-yl-4-nitrophenol 在 溶剂黄146 、 锌 、 氨 作用下， 以 水 为溶剂， 反应 1.5h， 生成 4-氨基-2-苯并噁唑-2-苯酚
  参考文献：
  名称：

  BENZOXAZOLE AND BENZOTHIAZOLE COMPOUNDS AND METHODS THEREFOR

  摘要：

  公式（I）的化合物：其中R1选择自由基团，包括具有2至12个碳原子的脂肪基，具有3至20个碳原子的芳香基，和具有3至20个碳原子的环脂肪基；但R1不是—C6H5或—NH—C10H7；R2和R3独立选择自由基团，包括羟基，卤原子，具有2至12个碳原子的脂肪基，具有3至20个碳原子的芳香基，和具有3至20个碳原子的环脂肪基；X是氧原子或硫原子；“n”的值为0至4；“m”的值为0至3。

  公开号：

  US20080081913A1
• 作为产物：
  描述：

  间硝基苯甲酰氯 在 sodium persulfate 、 甲烷磺酸 、 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.0h， 生成 2-benzoxazol-2-yl-4-nitrophenol
  参考文献：
  名称：

  Palladium catalyzed C_sp2–H activation for direct aryl hydroxylation: the unprecedented role of 1,4-dioxane as a source of hydroxyl radicals

  摘要：

  直接芳香族羟基化已通过使用多功能引导基团通过前所未有的1,4-二氧六环的羟基转移实现钯催化的Csp2-H活化。

  DOI：

  10.1039/c4cc06864e

文献信息

• A Magnetic Heterogeneous Biocatalyst Composed of Immobilized Laccase and 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) for Green One-Pot Cascade Synthesis of 2-Substituted Benzimidazole and Benzoxazole Derivatives under Mild Reaction Conditions
  作者：Mehdi Mogharabi-Manzari、Mahshid Kiani、Sima Aryanejad、Somaye Imanparast、Mohsen Amini、Mohammad Ali Faramarzi

  DOI：10.1002/adsc.201800459

  日期：2018.9.17

  reagent. The prepared catalyst was used to synthesize 12 benzoxazole and benzimidazole derivatives. The one‐pot, two‐step enzymatic aerobic oxidation reaction included the condensation of in situ‐produced salicylaldehyde derivatives with aromatic amines, followed by an enzymatic dehydrogenation process. Optimal reaction conditions consisted of a citrate buffer (10 mM, pH 4.5) at 40 °C for an incubation

  通过将化学和生化物种固定在磁性纳米颗粒上，可重复使用的高性能多相催化剂的设计可简化，快速且清洁的分离过程，从而提高了催化系统的效率。使用戊二醛作为偶联剂，将漆酶和4-氨基-2,2,6,6-四甲基哌啶-1-氧基分别固定在胺官能化的氧化铁（II，III）纳米粒子上。所制备的催化剂用于合成12个苯并恶唑和苯并咪唑衍生物。一锅，两步酶促好氧氧化反应包括原位缩合反应。用芳族胺制备水杨醛衍生物，然后进行酶促脱氢过程。最佳反应条件包括在40°C下柠檬酸缓冲液（10 mM，pH 4.5）孵育10 h和包含固定化漆酶（80 mg，100 U）和固定化2,2,6,6-的非均相催化剂四甲基哌啶-1-氧基（TEMPO）（40 mg，2 mol％）。10次​​运行后，催化剂保留了其初始活性的85％以上。除了可以重复使用而不会对性能造成重大损失外，该催化系统的环保特性还包括其高催化活性和使用外部磁体从反应混合物中回收的便捷性。
• Half-sandwich chromium(III) complexes containing salicylbenzoxazole and salicylbenzothiazole ligands for ethylene polymerization
  作者：Hui Liu、Suting Xu、Xiaochao Shi

  DOI：10.1016/j.inoche.2021.108885

  日期：2021.11

  Half-sandwich chromium(III) complexes bearing salicylbenzoxazole ligands 2a-2f [L = R-2-(benzo[d]xazol-2-yl)-phenol (R = H (2a), R = 6-CH3 (2b), R = 6-tBu (2c), R = 4-OCH3 (2d), R = 4-Cl (2e), R = 4-NO2 (2f)] and salicylbenzothiazole ligands 3a-3f [L = R-2-(benzo[d]xazol-2-yl)-phenol (R = H (3a), R = 6-CH3 (3b), R = 6-tBu (3c), R = 4-OCH3 (3d), R = 4-Cl (3e), R = 4-NO2 (3f)] were synthesized by the

  带有水杨基苯并恶唑配体2a - 2f [L = R-2-(苯并[d]恶唑-2-基)-苯酚 (R = H ( 2a ), R = 6-CH 3 ( 2b) ), R = 6- t Bu ( 2c ), R = 4-OCH 3 ( 2d ), R = 4-Cl ( 2e ), R = 4-NO 2 ( 2f )] 和水杨基苯并噻唑配体3a - 3f [L = R-2-(benzo[d]xazol-2-yl)-phenol (R = H ( 3a ), R = 6-CH 3 ( 3b ), R = 6- t Bu ( 3c ), R = 4-OCH 3( 3d ), R = 4-Cl ( 3e ), R = 4-NO 2 ( 3f )]是通过CpCrCl 2 (THF)和相应配体的钠盐在-78℃下在THF中的脱盐反应合成的℃。配合物3a和3e的分子结构由单晶 X 射线晶体学分析证实。在少量AlEt
• AUTHENTICATABLE ARTICLES AND METHODS THEREFOR
  申请人：Chauhan Yogendrasinh Bharatsinh

  公开号：US20080081210A1

  公开（公告）日：2008-04-03

  An article comprising the compound of Formula (I): wherein R 1 is selected from the group consisting of an aliphatic functionality having 1 to 12 carbons, an aromatic functionality having 3 to 20 carbons, and a cycloaliphatic functionality having 3 to 20 carbons; R 2 and R 3 are independently selected from the group consisting of a hydroxyl group, a halogen atom, an aliphatic functionality having 1 to 12 carbons, an aromatic functionality having 3 to 20 carbons, and a cycloaliphatic functionality having 3 to 20 carbons; Y is either an oxygen atom or a sulfur atom; “n” has a value of 0 to 4; and “m” has a value of 0 to 3.

  本文涉及一种化合物，其化学式为（I）：其中R1选自具有1到12个碳的脂肪基、具有3到20个碳的芳香基和具有3到20个碳的环烷基的群组之一；R2和R3独立地选自具有1到12个碳的脂肪基、具有3到20个碳的芳香基和具有3到20个碳的环烷基的群组之一，以及羟基、卤素原子；Y是氧原子或硫原子；“n”的值为0到4；“m”的值为0到3。
• Somayajulu; Rao, Current Science, 1956, vol. 25, p. 86
  作者：Somayajulu、Rao

  DOI：——

  日期：——
• In-vitro Anti-cancer assay and apoptotic cell pathway of newly synthesized benzoxazole-N-heterocyclic hybrids as potent tyrosine kinase inhibitors
  作者：Sulaksha Desai、Vidya Desai、Sunil Shingade

  DOI：10.1016/j.bioorg.2019.103382

  日期：2020.1

  A series of benzoxazole-N-heterocyclic hybrids have been synthesized by a one-pot strategy. Molecular docking study revealed that such compounds have the ability to inhibit enzyme protein tyrosine kinase. The findings of this work have been the successful synthesis of benzoxazole scaffolds, featuring hybrids of benzoxazole with quinoline and quinoxaline respectively. The molecular docking studies have showed these compounds to be inhibitors of tyrosine kinase enzyme which triggers growth of cancer cells. The cytotoxicity study of compounds 4a-f showed better potency against breast cancer cell lines MCF-7 and MDA-MB-231 in contrast to oral and lung cancer cell lines KB and A549. The tyrosine kinase activity was measured using Universal Tyrosine Kinase Assay kit using horseradish peroxide (HRP)-conjugated anti-phosphotyrosine kinase solution as a substrate. The compounds 4c exhibited maximum inhibition in the activity of enzyme tyrosine kinase with IC50 value 0.10 +/- 0.16 mu M, than other compounds which were studied and thus proved to be inhibitors of enzyme tyrosine kinase. The selective index of all four compounds was found out to be greater than two, indicating the non-toxic behaviour, i.e. good anti-cancer activity. Further, fluorescence microscopic study helped to characterize the mode of cell death, which was found to be late apoptosis as indicated by the orange fluorescence. The SAR analysis has also been carried out.