2-iodo-N-[2-[(2-iodophenyl)methylamino]-2-oxoethyl]-N-methylbenzamide | 638195-28-5

• 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: 2-iodo-N-[2-[(2-iodophenyl)methylamino]-2-oxoethyl]-N-methylbenzamide
• CAS: 638195-28-5
• 化学式: C₁₇H₁₆I₂N₂O₂
• 分子量: 534.135
• InChiKey: BXSYIZQLRKNGCW-UHFFFAOYSA-N

物化性质

• 沸点：
  648.4±55.0 °C(Predicted)
• 密度：
  1.851±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-iodo-N-[2-[(2-iodophenyl)methylamino]-2-oxoethyl]-N-methylbenzamide 在 potassium acetate 、 palladium diacetate 、 苯硼酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以90%的产率得到7-Methyl-7,10-diazatetracyclo[8.7.1.05,18.012,17]octadeca-1(18),2,4,12,14,16-hexaene-6,9-dione
  参考文献：
  名称：

  钯催化的多米诺骨牌分子内N-芳基化/分子间CC键形成，用于合成功能化的苯二氮杂二酮。

  摘要：

  已经开发了涉及分子内N-芳基化和分子间Heck反应的发散和区域​​控制的Pd催化的多米诺骨牌序列，可快速进入官能化的苯并二氮杂-2,5-二酮3。起始原料是通过Ugi四组分反应合成的。记录了双孢环6的空前X射线结构。

  DOI：

  10.1021/ol7029799
• 作为产物：
  描述：

  聚合甲醛 、 2-碘苯甲酸 、 甲胺 、 o-iodobenzyl isonitrile 以 甲醇 为溶剂， 生成 2-iodo-N-[2-[(2-iodophenyl)methylamino]-2-oxoethyl]-N-methylbenzamide
  参考文献：
  名称：

  钯催化的多米诺骨牌分子内N-芳基化/分子间CC键形成，用于合成功能化的苯二氮杂二酮。

  摘要：

  已经开发了涉及分子内N-芳基化和分子间Heck反应的发散和区域​​控制的Pd催化的多米诺骨牌序列，可快速进入官能化的苯并二氮杂-2,5-二酮3。起始原料是通过Ugi四组分反应合成的。记录了双孢环6的空前X射线结构。

  DOI：

  10.1021/ol7029799

文献信息

• Palladium- and Copper-Catalyzed Synthesis of Medium- and Large-Sized Ring-Fused Dihydroazaphenanthrenes and 1,4-Benzodiazepine-2,5-diones. Control of Reaction Pathway by Metal-Switching
  作者：Guylaine Cuny、Michèle Bois-Choussy、Jieping Zhu

  DOI：10.1021/ja047472o

  日期：2004.11.1

  Methods for the synthesis of dihydroazaphenanthrene fused to macrocycles (2) and medium-ring heterocycles (4), as well as 1,4-benzodiazepine-2,5-diones (5), are developed. A distinctly different catalytic property of palladium and copper catalysts was uncovered that leads to the development of a divergent synthesis of two different heterocyclic scaffolds from the same starting materials, simply by metal-switching. Thus, starting from linear amide 3, palladium acetate triggers a domino intramolecular N-arylation/ C-H activation/aryl-aryl bond-forming process to provide 4, while copper iodide promotes only the intramolecular N-arylation reaction leading to 5. In combination with the Ugi multicomponent reaction (Ugi-4CR) for the preparation of the linear amides, a two-step synthesis of either the 5,6-dihydro-8H-5,7a-diazacyclohepta[jk]phenanthrene-4,7-dione (4) or 1,4-benzodiazepine-2,5-diones (5), by appropriate choice of metal catalyst, is subsequently developed from very simple starting materials.
• One-Pot Synthesis of Polyheterocycles by a Palladium-Catalyzed Intramolecular N-Arylation/CH Activation/Aryl–Aryl Bond-Forming Domino Process
  作者：Guylaine Cuny、Michèle Bois-Choussy、Jieping Zhu

  DOI：10.1002/anie.200351923

  日期：2003.10.13
• Palladium-Catalyzed Domino Intramolecular N-Arylation/Intermolecular C−C Bond Formation for the Synthesis of Functionalized Benzodiazepinediones
  作者：Angela Salcedo、Luc Neuville、Christophe Rondot、Pascal Retailleau、Jieping Zhu

  DOI：10.1021/ol7029799

  日期：2008.3.1

  A divergent and regiocontrolled Pd-catalyzed domino sequence involving an intramolecular N-arylation and an intermolecular Heck reaction has been developed, providing rapid access to functionalized benzodiazepine-2,5-diones 3. The starting materials were synthesized by the Ugi four-component reaction. An unprecedented X-ray structure of bispalladacycle 6 was documented.

  已经开发了涉及分子内N-芳基化和分子间Heck反应的发散和区域​​控制的Pd催化的多米诺骨牌序列，可快速进入官能化的苯并二氮杂-2,5-二酮3。起始原料是通过Ugi四组分反应合成的。记录了双孢环6的空前X射线结构。