N-(2-氯苯基)吡啶-3-甲酰胺 | 75075-31-9

• 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-氯苯基)吡啶-3-甲酰胺
• 英文名称: N-(2-chlorophenyl)-3-pyridinecarboxamide
• 英文别名: N-(2-chlorophenyl)nicotinamide；N-(2-chlorophenyl)pyridine-3-carboxamide
• CAS: 75075-31-9
• 化学式: C₁₂H₉ClN₂O
• mdl: MFCD00227535
• 分子量: 232.669
• InChiKey: HWBPWTZNDRKRHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  290.8±20.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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-氯苯基)吡啶-3-甲酰胺 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 21.0h， 以37.3%的产率得到2-吡啶-3-基-1,3-苯并恶唑
  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
• 作为产物：
  描述：

  烟酸 在 氯化亚砜 、 二乙基异丙基胺 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 48.0h， 生成 N-(2-氯苯基)吡啶-3-甲酰胺
  参考文献：
  名称：

  An organometallic complex revealing an unexpected, reversible, temperature induced SC–SC transformation

  摘要：

  一种可逆的、温度驱动的相变换现象在约180K时发生，以单晶到单晶的方式观察到了一种基于fac-Re(CO)3核心的单金属过渡金属配位络合物，其中包含一个螯合的2,2'-联吡啶单元和一个卤代的N-(4-碘苯基)烟酰胺轴向共配体。

  DOI：

  10.1039/c4ce00070f

文献信息

• Direct Use of Copper-Containing Minerals in Goldberg Arylation of Amides
  作者：Gábor Györke、András Dancsó、Balázs Volk、László Bezúr、Dávid Hunyadi、Imre Szalóki、Mátyás Milen

  DOI：10.1007/s10562-022-03989-2

  日期：2023.2
• LETTAU, H.;MUELLER, J.;BERGMANN, I.;SCHUBERT, H.;SEEWALD, I.;WEISER, H.
  作者：LETTAU, H.、MUELLER, J.、BERGMANN, I.、SCHUBERT, H.、SEEWALD, I.、WEISER, H.

  DOI：——

  日期：——