N-(2-溴苯基)-4-吡啶羧酰胺 | 252930-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-溴苯基)-4-吡啶羧酰胺
• 英文名称: N-(2-bromophenyl)-4-pyridinecarboxamide
• 英文别名: N-(2-bromophenyl)pyridine-4-carboxamide
• CAS: 252930-61-3
• 化学式: C₁₂H₉BrN₂O
• mdl: MFCD02918241
• 分子量: 277.12
• InChiKey: MEGGLDYOLRNAOP-UHFFFAOYSA-N

物化性质

• 沸点：
  309.2±22.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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-溴苯基)-4-吡啶羧酰胺 在 copper(l) iodide 、 4-phenyl-1-(3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)-1H-1,2,3-triazole 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以96%的产率得到2-吡啶-4-基-1,3-苯并恶唑
  参考文献：
  名称：

  糖基三唑配体存在下Cu（I）催化C-杂原子偶联反应合成苯并唑

  摘要：

  糖基三唑可以方便地获得，并且包含多个金属结合单元，可以协助金属介导的催化作用。d-葡萄糖的叠氮化物衍生物已被转化为它们各自的芳基三唑，并被筛选为通过铜催化的分子内Ullmann型C-杂原子偶联合成2-取代的苯并稠合的唑和苯并咪唑并喹唑啉酮的配体。对于这种容易获得的催化体系，获得了多种苯并稠合杂环的良好或优异的产率。

  DOI：

  10.1021/acscombsci.9b00004
• 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-溴苯基)-4-吡啶羧酰胺
  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

• Photocatalyst- and Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp²)–S Formation
  作者：Hao Wang、Qi Wu、Jian-Dong Zhang、Hai-Yan Li、Hong-Xi Li

  DOI：10.1021/acs.orglett.1c00235

  日期：2021.3.19
• Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
  作者：Nidhi Mishra、Anoop S. Singh、Anand K. Agrahari、Sumit K. Singh、Mala Singh、Vinod K. Tiwari

  DOI：10.1021/acscombsci.9b00004

  日期：2019.5.13

  and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles

  糖基三唑可以方便地获得，并且包含多个金属结合单元，可以协助金属介导的催化作用。d-葡萄糖的叠氮化物衍生物已被转化为它们各自的芳基三唑，并被筛选为通过铜催化的分子内Ullmann型C-杂原子偶联合成2-取代的苯并稠合的唑和苯并咪唑并喹唑啉酮的配体。对于这种容易获得的催化体系，获得了多种苯并稠合杂环的良好或优异的产率。
• 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.