N-(4-碘-2-甲氧基吡啶-3-基)三甲基乙酰胺 | 131653-62-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(4-碘-2-甲氧基吡啶-3-基)三甲基乙酰胺
• 英文名称: 2,2-dimethyl-N-(4-iodo-2-methoxy-3-pyridyl)propanamide
• 英文别名: 4-iodo-2-methoxy-3-pivaloylaminopyridine；N-(4-Iodo-2-methoxypyridin-3-yl)pivalamide；N-(4-iodo-2-methoxypyridin-3-yl)-2,2-dimethylpropanamide
• CAS: 131653-62-8
• 化学式: C₁₁H₁₅IN₂O₂
• 分子量: 334.157
• InChiKey: WLRFICVEMCFVMF-UHFFFAOYSA-N

物化性质

• 沸点：
  385.4±42.0 °C(Predicted)
• 密度：
  1.580±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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-碘-2-甲氧基吡啶-3-基)三甲基乙酰胺 在 四(三苯基膦)钯 吡啶 、 三溴化硼 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 51.33h， 生成 2-<4-(2-N,N-diisopropylcarbamoylphenyl)-3-pivaloylamino>pyridyl triflate
  参考文献：
  名称：

  Convergent synthesis of the streptonigrin alkaloid skeleton. Directed orthometalation connection to aryl-aryl cross-coupling

  摘要：

  A convergent synthesis of 2-[2-(4-phenyl-3-pivaloylamino) pyridyl]quinolines, the streptonigrin alkaloid skeleton, is reported. The methodology involves independent elaboration of the three main building blocks by metalation and two coupling reactions catalyzed by palladium.

  DOI：

  10.1016/s0040-4020(01)92191-x
• 作为产物：
  描述：

  N-(2-甲氧基吡啶-3-基)三甲基乙酰胺 在 正丁基锂 、 四甲基乙二胺 、 碘 作用下， 以71%的产率得到N-(4-碘-2-甲氧基吡啶-3-基)三甲基乙酰胺
  参考文献：
  名称：

  Metallation in connection with cross-coupling reactions. Coupling of hindered aryls for the synthesis of 4-phenylpyridines as part of Streptonigrin and Lavendamycin analogues

  摘要：

  The synthesis of the C-D ring system of Streptonigrin and Lavendamycin alkaloid analogues by cross-coupling under Suzuki's conditions has been studied. Steric hindrance is the main problem. It has been solved either by using strong bases or working in a sealed tube under pressure.

  DOI：

  10.1016/0022-328x(95)05979-y

文献信息

• Marsais, Francis; Rovera, Jean-Claude; Turck, Alain, Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2611 - 2612
  作者：Marsais, Francis、Rovera, Jean-Claude、Turck, Alain、Godard, Alain、Queguiner, Guy

  DOI：——

  日期：——
• MARSAIS, FRANCIS;ROVERA, JEAN-CLAUDE;TURCK, ALAIN;GODARD, ALAIN;QUEQUINER+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2611-2612
  作者：MARSAIS, FRANCIS、ROVERA, JEAN-CLAUDE、TURCK, ALAIN、GODARD, ALAIN、QUEQUINER+

  DOI：——

  日期：——
• Convergent synthesis of the streptonigrin alkaloid skeleton. Directed orthometalation connection to aryl-aryl cross-coupling
  作者：Alain Godard、Jean-Claude Rovera、Francis Marsais、Nelly Plé、Guy Quéguiner

  DOI：10.1016/s0040-4020(01)92191-x

  日期：1992.1

  A convergent synthesis of 2-[2-(4-phenyl-3-pivaloylamino) pyridyl]quinolines, the streptonigrin alkaloid skeleton, is reported. The methodology involves independent elaboration of the three main building blocks by metalation and two coupling reactions catalyzed by palladium.
• Metallation in connection with cross-coupling reactions. Coupling of hindered aryls for the synthesis of 4-phenylpyridines as part of Streptonigrin and Lavendamycin analogues
  作者：A. Godard、P. Rocca、V. Pomel、L. Thomas-dit-Dumont、J.C. Rovera、J.F. Thaburet、F. Marsais、G. Quéguiner

  DOI：10.1016/0022-328x(95)05979-y

  日期：1996.6

  The synthesis of the C-D ring system of Streptonigrin and Lavendamycin alkaloid analogues by cross-coupling under Suzuki's conditions has been studied. Steric hindrance is the main problem. It has been solved either by using strong bases or working in a sealed tube under pressure.