tert-butyl (3-methyl-2-(pyridin-2-yl)phenyl)carbamate | 1440753-94-5

• 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 (3-methyl-2-(pyridin-2-yl)phenyl)carbamate
• 英文别名: tert-butyl N-(3-methyl-2-pyridin-2-ylphenyl)carbamate
• CAS: 1440753-94-5
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: DPFAGXNUXBEFJE-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：

  二碳酸二叔丁酯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 盐酸羟胺 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 tert-butyl (3-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

• A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C–H Amidation Using Azidoformates
  作者：Hyunwoo Kim、Gyeongtae Park、Juhyeon Park、Sukbok Chang

  DOI：10.1021/acscatal.6b01869

  日期：2016.9.2

  Described herein is the development of Ir(III)-catalyzed direct C–H amidation using azidoformates as a readily deprotectable amino source. Substrates with unactivated methyl C(sp3)–H and aromatic or olefinic C(sp2)–H bonds were smoothly reacted by the iridium-based catalyst system to provide the corresponding primary alkylamines and anilines upon the subsequent removal of N-protecting groups, such

  本文描述的是使用叠氮基甲酰胺作为易于脱保护的氨基源，对Ir（III）催化的直接C–H酰胺化的进展。具有未活化的甲基C（sp 3）-H和芳族或烯属C（sp 2）-H键的底物通过铱基催化剂体系顺利反应，随后去除N保护基后提供相应的伯烷基胺和苯胺，例如Boc，Fmoc，Cbz，pNZ或Troc。还介绍了简要的机械研究和综合应用。
• Rhodium-Catalyzed<i>N</i>-<i>tert</i>-Butoxycarbonyl (Boc) Amination by Directed CH Bond Activation
  作者：Julian Wippich、Nadina Truchan、Thorsten Bach

  DOI：10.1002/adsc.201600410

  日期：2016.6.30

  the indoloquinoline alkaloids quindoline and cryptolepine. The facile removal of the Boc protecting group was the key to the success of the syntheses. The scope of the reaction was extended to a C(sp3)H bond amination and to the amination of 2‐phenyloxazoline. For the amination of 2‐pyridin‐2‐ylbenzene a kinetic deuterium isotope effect of 2.0 was determined.

  ñ -叔丁氧羰基叠氮化物（BocN 3）被证明是用于定向引进一种高效和经济的来源Ñ -Boc保护的氨基转化成噻吩并苯核。2-吡啶-2-基噻吩（10个实例）的胺化产率为52–88％。对于各种苯的胺化（10个实例），记录的收率在54％至99％之间，而带有吸电子基团的底物的反应性得到了改善。该反应被用于吲哚喹啉碱生物碱喹多啉和隐肾上腺素的短总合成。Boc保护基的轻松去除是合成成功的关键。反应范围扩大到C（sp 3）H键胺化和2-苯基恶唑啉的胺化。对于2-吡啶-2-基苯胺的胺化，动力学氘同位素效应确定为2.0。
• <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.