N-((3-phenylisoxazol-5-yl)methylene)aniline | 857591-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((3-phenylisoxazol-5-yl)methylene)aniline
• 英文别名: N-phenyl-1-(3-phenyl-1,2-oxazol-5-yl)methanimine
• CAS: 857591-84-5
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: ACIGJJDOFSQKRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.39
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  庚醛 、 N-((3-phenylisoxazol-5-yl)methylene)aniline 在 碘 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到5-(3-pentylquinolin-2-yl)-3-phenylisoxazole
  参考文献：
  名称：

  Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity

  摘要：

  The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having a-hydrogen using molecular iodine as catalyst and which yielded 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives 4. All the final compounds 4 were screened against four human cancer cell lines (A549, COLO 205, MDA-MB 231 and PC-3) and among these compounds 4n showed potent cytotoxicity against all the cell lines at IC50 values of < 12 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.038
• 作为产物：
  描述：

  (3-苯基-5-异恶唑基)甲醇 在 Jones reagent 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 6.58h， 生成 N-((3-phenylisoxazol-5-yl)methylene)aniline
  参考文献：
  名称：

  Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity

  摘要：

  The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having a-hydrogen using molecular iodine as catalyst and which yielded 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives 4. All the final compounds 4 were screened against four human cancer cell lines (A549, COLO 205, MDA-MB 231 and PC-3) and among these compounds 4n showed potent cytotoxicity against all the cell lines at IC50 values of < 12 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.038

文献信息

• Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles
  作者：Loïc R. E. Pantaine、John A. Milligan、Jennifer K. Matsui、Christopher B. Kelly、Gary A. Molander

  DOI：10.1021/acs.orglett.9b00602

  日期：2019.4.5

  Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated alkyl radicals possessing pendant leaving groups engage imines in C–C bond formation, and subsequent reduction of the intermediate nitrogen-centered radical triggers

  光氧化还原介导的自由基/极性交叉（RPC）过程为环状分子的合成提供了新途径。该过程已实现用于构建中型饱和氮杂环。光催化产生的具有侧离去基团的烷基自由基与亚胺形成C-C键，随后中间氮中心自由基的还原引发阴离子闭环。借助可见光照射，可以在温和的氧化还原中性条件下制备取代的吡咯烷、哌啶和氮杂环庚烷。
• Photoinduced Diastereoselective Aminoalkylation of Cubanes
  作者：Guillaume Levitre、Sebastian Keess、Gary A. Molander

  DOI：10.1021/acs.orglett.3c01223

  日期：2023.6.2

  but the development of suitable conditions for alkylation of cubanes is quite challenging. Herein, a photoinduced method for aminoalkylation of cubanes is reported. The benign conditions reported allow the incorporation of a wide variety of (hetero)arylimine reaction partners with broad functional group tolerance and high diastereoselectivity.

  刚性、非共轭碳氢化合物的独特性质为设计用于各种应用的分子结构单元提供了许多机会，但开发适合立方烷烷基化的条件非常具有挑战性。在此，报道了一种用于立方烷氨基烷基化的光诱导方法。报告的良性条件允许掺入各种具有广泛官能团耐受性和高非对映选择性的（杂）芳基亚胺反应伙伴。
• A General and Modular Approach to BCP Alkylamines via Multicomponent Difunctionalization of [1.1.1]Propellane
  作者：Weichen Huang、Yongxiang Zheng、Sebastian Keess、Gary A. Molander

  DOI：10.1021/jacs.2c13298

  日期：2023.3.8
• Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity
  作者：P. Sambasiva Rao、C. Kurumurthy、B. Veeraswamy、Y. Poornachandra、C. Ganesh Kumar、B. Narsaiah

  DOI：10.1016/j.bmcl.2014.01.038

  日期：2014.3

  The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having a-hydrogen using molecular iodine as catalyst and which yielded 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives 4. All the final compounds 4 were screened against four human cancer cell lines (A549, COLO 205, MDA-MB 231 and PC-3) and among these compounds 4n showed potent cytotoxicity against all the cell lines at IC50 values of < 12 mu M. (C) 2014 Elsevier Ltd. All rights reserved.