tert-butyl (4-methyl-2-(pyridin-2-yl)phenyl)carbamate | 1440753-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl (4-methyl-2-(pyridin-2-yl)phenyl)carbamate
• 英文别名: tert-butyl N-(4-methyl-2-pyridin-2-ylphenyl)carbamate
• CAS: 1440753-99-0
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: IHMGAEDHLJJQAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴吡啶 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 potassium phosphate tribasic heptahydrate 、 palladium diacetate 作用下， 以 水 、 异丙醇 为溶剂， 反应 16.0h， 生成 tert-butyl (4-methyl-2-(pyridin-2-yl)phenyl)carbamate
  参考文献：
  名称：

  [RhCp*Cl₂]₂-Catalyzed Directed N-Boc Amidation of Arenes “on Water”

  摘要：

  Rhodium(III) catalysis on water is effective for directed C-H amidation of arenes. The catalytic process is promoted by OH groups present on the hydrophobic water surface and is inefficient in all (most) common organic solvents investigated so far. In the presence of easily prepared tert-butyl 2,4-dinitrophenoxycarbamate, a new and stable nitrene source, the on water reaction can efficiently provide the desired N-Boc-aminated products with good functional group tolerance.

  DOI：

  10.1021/acs.orglett.5b00392

文献信息

• <i>N</i>-Substituted Hydroxylamines as Synthetically Versatile Amino Sources in the Iridium-Catalyzed Mild C–H Amidation Reaction
  作者：Pitambar Patel、Sukbok Chang

  DOI：10.1021/ol501338h

  日期：2014.6.20

  N-Substituted hydroxylamines such as aroyloxy- or acyloxycarbamates were successfully employed as synthetically versatile amino precursors in the iridium-catalyzed direct C-H amidation of arenes. The reaction proceeds smoothly at room temperature over a broad range of substrates with high functional group tolerance to afford N-substituted arylamine products.
• Cobalt(III)-Catalyzed C–H Amidation of Arenes using Acetoxycarbamates as Convenient Amino Sources under Mild Conditions
  作者：Pitambar Patel、Sukbok Chang

  DOI：10.1021/cs501860b

  日期：2015.2.6

  The Co(III)-catalyzed direct C-H amidation of arenes has been developed using O-acylcarbamates as a convenient amino source. This reaction proceeded in high efficiency under external oxidant-free conditions with a broad range of arene substrates, including 6-arylpurines bearing sensitive functional groups, thus furnishing synthetically versatile arene N-carbamate products.
• Rh[III]-Catalyzed C–H Amidation Using Aroyloxycarbamates To Give <i>N</i>-Boc Protected Arylamines
  作者：Christoph Grohmann、Honggen Wang、Frank Glorius

  DOI：10.1021/ol401209f

  日期：2013.6.21

  The Rh(III)-catalyzed amidation of C(sp(2))-H bonds by the use of electron-deficient aroyloxycarbamates as efficient electrophilic amidation partners is reported. The reaction proceeded under mild conditions with broad functional group tolerance, and pyridine and O-methyl hydroxamic acids serve as efficient directing groups, giving access to valuable N-Boc protected arylamines (also Fmoc and Cbz). Preliminary mechanistic experiments are discussed.