N‐(2‐iodophenyl)isonicotinamide | 252930-62-4

• 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‐(2‐iodophenyl)isonicotinamide
• 英文别名: N-(2-iodophenyl)-4-pyridinecarboxamide；N-(2-iodophenyl)pyridine-4-carboxamide
• CAS: 252930-62-4
• 化学式: C₁₂H₉IN₂O
• mdl: MFCD00805691
• 分子量: 324.121
• InChiKey: XXAFKATVVNREPP-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  325.9±22.0 °C(Predicted)
• 密度：
  1.765±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N‐(2‐iodophenyl)isonicotinamide 在 caesium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到2-吡啶-4-基-1,3-苯并恶唑
  参考文献：
  名称：

  纳米磁铁矿支持的N-杂环卡宾-铜配合物与翼尖二茂铁的分子内芳构化

  摘要：

  纳米磁铁矿负载的N-杂环卡宾-铜与翼尖二茂铁配合物已通过多步程序制备。该复合物具有多种分析技术的特征，例如傅立叶变换红外（FT-IR），傅立叶变换拉曼（FT-Raman），X射线光电子能谱（XPS），X射线衍射（XRD），透射电子显微镜（ TEM）和振动样品磁力计（VSM）分析。该复合物的催化活性已在异质条件下的邻碘苯胺的分子内芳基化中得到了利用。该复合物可以成功回收多达十二个连续循环。

  DOI：

  10.1002/aoc.5066
• 作为产物：
  描述：

  异烟酸 在 吡啶 、 氯化亚砜 作用下， 反应 2.0h， 生成 N‐(2‐iodophenyl)isonicotinamide
  参考文献：
  名称：

  Synthesis of 2-Pyridinylbenzoxazole:  Mechanism for the Intramolecular Photosubstitution of the Haloarene with the Carbonyl Oxygen of the Amide Bond in Basic Medium

  摘要：

  2-Pyridinylbenzoxazole derivatives have been synthesized by the intramolecular photosubstitution reaction of N-(2-halophenyl)pyridinecarboxamide (1 and 2) with its amide bond in basic medium. In neutral medium both intramolecular photosubstitution and photoreduction reactions occurred. In the photosubstitution reaction a singlet state of the o-haloarene is involved, whereas in the photoreduction a triplet state of the o-haloarene is involved; oxygen inhibited the photoreduction but not the photosubstitution. The relative rate studies showed that a base accelerates the photosubstitution reaction but decelerates the photoreduction. o-Iodoarenecarboxamide is more reactive than o-bromoarenecarboxamide, which in turn is more reacitive than o-chloroarenecarboxamide. UV-vis absorption change in the presence of a base showed that an imidol and/or imidolate anion is involved in the reaction. Several transient species, such as charge-transfer excited states and a cyclohexadienyl anion radical, have been identified from the photolysis of 1 and 2 in basic medium by laser flash photolysis. In neutral medium dibromide anion radical and a phenyl a radical were identified in addition to the above intermediates. On the basis of the photokinetic and laser flash photolysis studies, an intramolecular photosubstitution of N-(o-halophenyl)-pyridinecarboxamide with its amide bond occurs via an intramolecular S-N(ET)Ar* mechanism to afford 2-pyridinylbenzoxazole derivative, and the photoreduction proceeds via a free radical mechanism to give N-phenylpyridinecarboxamide.

  DOI：

  10.1021/jo9909498

文献信息

• Efficient palladium-catalyzed direct arylation of azines and diazines using ligand-free conditions
  作者：Luca Basolo、Egle M. Beccalli、Elena Borsini、Gianluigi Broggini

  DOI：10.1016/j.tet.2009.02.025

  日期：2009.4

  The use of the palladium-catalyzed direct arylation was successfully tested on different electron-deficient heterocycles. The results demonstrate the effectiveness of the method based on the intramolecular coupling reaction providing polyazacyclic systems. This new application was obtained by using ligand-free conditions with the mixture of Pd(OAc)(2) and TBAC as catalytic system. With suitable substrates different products arising from regioselective coupling were observed. (C) 2009 Elsevier Ltd. All rights reserved.