N-(2-(pyridin-2-yl)propan-2-yl)isonicotinamide | 1620193-83-0

• 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: N-(2-(pyridin-2-yl)propan-2-yl)isonicotinamide
• 英文别名: N-(2-pyridin-2-ylpropan-2-yl)pyridine-4-carboxamide
• CAS: 1620193-83-0
• 化学式: C₁₄H₁₅N₃O
• 分子量: 241.293
• InChiKey: ULYIGTIOTDKFJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-(pyridin-2-yl)propan-2-yl)isonicotinamide 在 copper diacetate 、 四丁基碘化铵 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以80%的产率得到3-hydroxy-N-(2-(pyridin-2-yl)propan-2-yl)isonicotinamide
  参考文献：
  名称：

  Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary

  摘要：

  A copper-mediated C-H hydroxylation of arenes and heteroarenes using our newly developed PIP directing group has been developed. This procedure is scalable and compatible with a wide range of functional groups and heteroarenes, providing an operationally simple protocol for the synthesis of o-hydroxybenzamides. The hydroxylation of nicotinamides gave 4-oxo-1,4-dihydropyridine-3-carboxamides selectively. Preliminary mechanistic studies implicate that a basic ligand-enabled, irreversible, rate-determining CMD step is most likely involved in this process.

  DOI：

  10.1021/ol5016064
• 作为产物：
  描述：

  异烟酸 、 2-(吡啶-2-基)-2-丙胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-(pyridin-2-yl)propan-2-yl)isonicotinamide
  参考文献：
  名称：

  铜/银介导的未活化（杂）芳基C的直接邻乙氧基化？末端炔烃的H键

  摘要：

  已开发出未活化的芳基CH键与末端炔烃的铜/银介导的氧化邻乙炔基化反应。该反应使用可移动的PIP导向基团，并具有广泛的底物范围，高官能团耐受性以及与各种杂环的相容性，从而提供了芳基炔烃的高效合成方法。此过程亮点铜催化剂的潜力，促进独特的，合成使Ç 摆在贵金属催化的当前范围之外ħ官能化反应。

  DOI：

  10.1002/chem.201405594

文献信息

• Copper-Mediated Thiolation of Unactivated Heteroaryl C−H Bonds with Disulfides under Ligand- and Metal-Oxidant-Free Conditions
  作者：Ya Li、Yue-Jin Liu、Bing-Feng Shi

  DOI：10.1002/adsc.201700949

  日期：2017.12.11

  sulfenylated heteroarenes were synthesized by a copper‐mediated C−H thiolation, which was assisted by a 2‐(pyridin‐2‐yl)isopropylamine (PIP‐amine) directing group. The reaction features a broad substrate scope, good functional group tolerance, ligand‐ and metal‐oxidant‐free conditions, exceptional compatibility with aliphatic disulfides, and excellent yields, providing a highly efficient approach to

  通过铜介导的CH巯基化反应合成了各种亚磺化杂芳基，并辅以2-（吡啶-2-基）异丙胺（PIP-胺）导向基团。该反应具有广泛的底物范围，良好的官能团耐受性，无配体和金属氧化剂的条件，与脂肪族二硫化物的优异相容性以及优异的收率，为生物学上重要的亚磺化杂芳烃提供了一种高效方法。
• Ni(<scp>ii</scp>)-catalyzed dehydrative alkynylation of unactivated (hetero)aryl C–H bonds using oxygen: a user-friendly approach
  作者：Yan-Hua Liu、Yue-Jin Liu、Sheng-Yi Yan、Bing-Feng Shi

  DOI：10.1039/c5cc03729h

  日期：——

  Ni(ii)-catalyzed dehydrative alkynylation of unactivated C(sp²)–H bonds with terminal alkynes under atmospheric pressure of oxygen is described.

  使用Ni(ii)催化的未活化的C(sp2)-H键与末端炔烃进行脱水炔基化反应，在氧气大气压下进行。
• Copper-catalyzed oxidative C–H/C–H cross-coupling of benzamides and thiophenes
  作者：Sheng Zhao、Jun Yuan、Yi-Chen Li、Bing-Feng Shi

  DOI：10.1039/c5cc05058h

  日期：——

  A copper-catalyzed oxidative C–H/C–H cross-coupling of benzamides and thiophenes is described.

  一种以铜为催化剂的苯甲酰胺和噻吩的氧化C–H/C–H交叉偶联反应被描述。
• Cu(II)-Mediated C–S/N–S Bond Formation via C–H Activation: Access to Benzoisothiazolones Using Elemental Sulfur
  作者：Fa-Jie Chen、Gang Liao、Xin Li、Jun Wu、Bing-Feng Shi

  DOI：10.1021/ol5027156

  日期：2014.11.7

  A copper-mediated CS/NS bondforming reaction via CH activation that uses elemental sulfur has been developed. The addition of TBAI was found to be crucial for the success of this transformation. The method is scalable, shows excellent functional group tolerance, and is compatible with heterocycle substrates, providing efficient and practical access to benzoisothiazolones. The direct diversification of the benzoisothiazolone products into a variety of sulfur-containing compounds is also demonstrated.
• Copper-/Silver-Mediated Arylation of C(sp²)–H Bonds with 2-Thiophenecarboxylic Acids
  作者：Sheng Zhao、Yue-Jin Liu、Sheng-Yi Yan、Fa-Jie Chen、Zhuo-Zhuo Zhang、Bing-Feng Shi

  DOI：10.1021/acs.orglett.5b01560

  日期：2015.7.2

  A copper/silver-mediated arylation of (hetero)aryl C-H bonds with 2-thiophenecarboxylic acids has been achieved. The protocol features a broad substrate scope and high functional group tolerance. Preliminary mechanistic studies indicate that a cascade protodecarboxylation/dehydrogenative coupling process is likely involved.