3-phenyl-2H-chromen-2-imine | 67231-69-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-phenyl-2H-chromen-2-imine
• 英文别名: 3-phenyl(iminocoumarine)；3-phenyliminocoumarin；3-phenyl-chromen-2-one-imine；3-Phenyl-chromen-2-on-imin；2-Imino-3-phenyl-2H-chromen；3-Phenyl iminochromene；3-phenylchromen-2-imine
• CAS: 67231-69-0
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: SEMOZQZSHHXJOR-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  344.1±52.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 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：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氟苯硼酸 、 3-phenyl-2H-chromen-2-imine 在 氧气 、 copper(II) acetate monohydrate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以79%的产率得到(Z)-N-(4-fluorophenyl)-3-phenyl-2H-chromen-2-imine
  参考文献：
  名称：

  在有氧条件下铜催化亚氨基 C-N 键与芳基硼酸的形成

  摘要：

  开发了一种铜催化的、无配体和无碱的 C-N 交叉偶联反应，即在室温下，在无毒乙醇溶剂中，亚氨基色烯与芳基硼酸在空气中的反应。发现产品产率良好至中等。敏感亚胺官能团的保守性意味着该协议的温和性

  DOI：

  10.1055/s-0035-1561382
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 乙醚 作用下， 生成 3-phenyl-2H-chromen-2-imine
  参考文献：
  名称：

  Houben; Pfankuch, Chemische Berichte, 1926, vol. 59, p. 1601

  摘要：

  DOI：

文献信息

• Synthesis of New<i>bis</i>-Iminocoumarins by Schmidt Reaction Catalyzed by Ion-Exchange Resins
  作者：Houcine Ammar、Mehdi Fakhfakh、Yves Le Bigot、Rachid El Gharbi

  DOI：10.1081/scc-120020190

  日期：2003.6

  Abstract A new synthetic route to bis-iminocoumarins is proposed which involves the synthesis of iminocoumarins from reaction of 2-hydroxybenzaldehydes with arylacetonitriles and their coupling with aromatic diamines. Ion-exchange resins were used as catalysts in both steps of this synthesis. The reaction parameters were varied and obtained using Amberlyst 15 resin in cyclohexane at 80°C.

  摘要 提出了一种合成双亚氨基香豆素的新路线，该路线包括由2-羟基苯甲醛与芳基乙腈反应并与芳香二胺偶联合成亚氨基香豆素。在该合成的两个步骤中都使用离子交换树脂作为催化剂。在 80°C 下使用 Amberlyst 15 树脂在环己烷中改变并获得反应参数。
• Polymer Supported Reagents: Novel Methodology for Selective and General Synthesis of Iminocoumarins
  作者：C. Mhiri、R. El Gharbi、Y. Le Bigot

  DOI：10.1080/00397919908085966

  日期：1999.10

  A selective synthesis of iminocoumarins 3 was accomplished, starting from salicylaldehydes 1 and nitriles 2, by the use of Amberlite IRA 900 resin as a polymeric solid support. The possibility of using various arylacetonitriles enhances the synthetic versatility of this strategy.
• Novel Synthesis of Bis-Iminocoumarins
  作者：H. Ammar、S. Abid、Y. Le Bigot、R. El Gharbi

  DOI：10.1080/00397911.2010.531370

  日期：2012.3.15

  Reaction of 3-aryl iminocoumarins with diacid chlorides as C-electrophilic reagents under mild conditions novel bis-iminocoumarins in good yields. When the reaction was performed with alkylene dibromides by heating them in toluene in the presence of IRA 900 resin, bis-ether compounds were obtained by way opening the pyranic ring. The structures of the product obtained were characterized by Fourier transform infrared, H-1 NMR, C-13 NMR, and elemental analysis.
• Iminocoumarin based fluorophores: Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol
  作者：Dnyaneshwar Kand、Prashant Sahebrao Mandal、Avdhoot Datar、Pinaki Talukdar

  DOI：10.1016/j.dyepig.2014.02.001

  日期：2014.7

  Off-on fluorescence probes for the detection of thiophenol were designed based on the reaction mechanism to ensure rapid sensing process. 2,4-Dinitrophenyisulfonyl based probes with iminocoumarin fluorophores were validated by theoretical calculations for their off-fluorescence states. Reaction of these probes with thiophenol released strong fluorescent iminocoumarin species with good response times. These results, upon comparing with reported probes, confirmed that higher pK(aH) values of the imino nitrogen of iminocoumarins are important for rapid sensing process. Reactivity of these probes was limited to only thiophenol and no reaction was observed with aliphatic thiols. The benzothiazole substituted probe displayed up to 260-fold fluorescence enhancement upon reaction with thiophenol. Sensing of the analyte by the probe was characterized by change in color from red to yellow and with appearance of the green fluorescence. A detection limit up to 6.9 x 10(-9) M was also determined for this probe. (C) 2014 Elsevier Ltd. All rights reserved.
• Kuhn; Weiser, Justus Liebigs Annalen der Chemie, 1956, vol. 600, p. 145
  作者：Kuhn、Weiser

  DOI：——

  日期：——