N-(2-bromophenyl)-N-methyl-4-pyridinecarboxamide | 252930-63-5

• 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-(2-bromophenyl)-N-methyl-4-pyridinecarboxamide
• 英文别名: 4-Pyridinecarboxamide, N-(2-bromophenyl)-N-methyl-；N-(2-bromophenyl)-N-methylpyridine-4-carboxamide
• CAS: 252930-63-5
• 化学式: C₁₃H₁₁BrN₂O
• 分子量: 291.147
• InChiKey: HSSYKVPZUXAMBT-UHFFFAOYSA-N

物化性质

• 沸点：
  408.2±41.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-bromophenyl)-N-methyl-4-pyridinecarboxamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以50%的产率得到6-methyl-benzo[c][2,7]naphthyridin-5(6H)-one
  参考文献：
  名称：

  利用自由基反应合成杂环化合物

  摘要：

  广义自由基反应已被用于合成杂环化合物，可以用作药物发现的配体。还已经尝试使在TBTH反应期间形成的氧化产物的形成合理化。

  DOI：

  10.1016/s0040-4039(02)01537-x
• 作为产物：
  描述：

  异烟酸 在 吡啶 、 氢氧化钾 、 氯化亚砜 作用下， 以 丙酮 为溶剂， 反应 2.08h， 生成 N-(2-bromophenyl)-N-methyl-4-pyridinecarboxamide
  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

• Synthesis of 2-Pyridinylbenzoxazole:  Mechanism for the Intramolecular Photosubstitution of the Haloarene with the Carbonyl Oxygen of the Amide Bond in Basic Medium
  作者：Yong-Tae Park、Chang-Hee Jung、Kwang-Wook Kim、Ho Sik Kim

  DOI：10.1021/jo9909498

  日期：1999.11.1

  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.
• Synthesis of heterocyclic compounds using radical reactions
  作者：A.K. Ganguly、C.H. Wang、M. David、P. Bartner、T.M. Chan

  DOI：10.1016/s0040-4039(02)01537-x

  日期：2002.9

  A generalised radical reaction has been used to synthesise heterocyclic compounds which could serve as ligands for drug discovery. Attempt also have been made to rationalise the formation of oxidation products formed during TBTH reaction.

  广义自由基反应已被用于合成杂环化合物，可以用作药物发现的配体。还已经尝试使在TBTH反应期间形成的氧化产物的形成合理化。