4-bromo-N-(2-(pyridin-2-yl)propan-2-yl)benzamide | 1620193-58-9

• 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: 4-bromo-N-(2-(pyridin-2-yl)propan-2-yl)benzamide
• 英文别名: 4-bromo-N-(2-pyridin-2-ylpropan-2-yl)benzamide
• CAS: 1620193-58-9
• 化学式: C₁₅H₁₅BrN₂O
• 分子量: 319.201
• InChiKey: PBTOMCZJKCPJOM-UHFFFAOYSA-N

物化性质

• 沸点：
  462.8±35.0 °C(predicted)
• 密度：
  1.365±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-N-(2-(pyridin-2-yl)propan-2-yl)benzamide 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 1.0h， 以94%的产率得到4-bromo-2-hydroxy-N-(2-(pyridin-2-yl)propan-2-yl)benzamide
  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：

  4-溴苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-bromo-N-(2-(pyridin-2-yl)propan-2-yl)benzamide
  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

• Nickel-Catalyzed Sulfonylation of C(<i>sp</i>²)-H Bonds with Sodium Sulfinates
  作者：Shuang-Liang Liu、Xue-Hong Li、Shu-Sheng Zhang、Sheng-Kai Hou、Guang-Chao Yang、Jun-Fang Gong、Mao-Ping Song

  DOI：10.1002/adsc.201700290

  日期：2017.7.3

  substrate scope and good functional group tolerance with high monosulfonylation selectivity. Besides arenes and heteroarenes, the reaction can also be extended to alkenes, providing diverse diaryl and alkyl aryl sulfones in high yields. Furthermore, a plausible Ni(I)/Ni(III) mechanism is outlined based on our experimental results and related precedents.

  描述了由（吡啶-2-基）异丙胺（PIP-胺）引导的亚磺酸钠对C（sp 2）-H键的首次镍催化邻位磺酰化反应。该策略展示了宽的底物范围和良好的官能团耐受性以及高的单磺酰化选择性。除了芳烃和杂芳烃之外，该反应还可以扩展至烯烃，以高收率提供各种二芳基和烷基芳基砜。此外，根据我们的实验结果和相关先例，概述了可能的Ni（I）/ Ni（III）机制。
• Nickel-catalyzed and benzoic acid-promoted direct sulfenylation of unactivated arenes
  作者：Ke Yang、Yuqi Wang、Xinyong Chen、Adnan A. Kadi、Hoong-Kun Fun、Hao Sun、Yan Zhang、Hongjian Lu

  DOI：10.1039/c4cc10431e

  日期：——

  A nickel-catalyzed direct sulfenylation of unactivated arenes using removable 2-(pyridine-2-yl)-isopropylamine as a directing group has been developed.

  一种镍催化的直接砜化反应已经开发出来，可以使用可移除的2-(吡啶-2-基)-异丙胺作为导向基对未活化的芳烃进行砜化。
• A sustainable and simple catalytic system for direct alkynylation of C(sp²)–H bonds with low nickel loadings
  作者：Yue-Jin Liu、Yan-Hua Liu、Sheng-Yi Yan、Bing-Feng Shi

  DOI：10.1039/c5cc01163a

  日期：——

  A sustainable and simple catalytic system for the atom-economical alkynylation of benzamides with low nickel loadings is described. No organic or metallic oxidants and expensive ligands are required. A broad range of benzamides and bromoalkynes bearing various synthetically useful functional groups are compatible with this reaction. The versatility of this operationally simple protocol has been further

  描述了一种可持续且简单的催化体系，用于低镍负载量的苯甲酰胺的原子经济烷基炔化反应。不需要有机或金属氧化剂和昂贵的配体。带有各种合成上有用的官能团的各种各样的苯甲酰胺和溴代炔与该反应相容。可操作的单和双炔基化进一步证明了该操作简单协议的多功能性。重要的是，底物/催化剂之比高达200，周转数达到196，突显了该方案在合成应用中的潜力。
• Nickel-catalyzed ortho-halogenation of unactivated (hetero)aryl C–H bonds with lithium halides using a removable auxiliary
  作者：Bei-Bei Zhan、Yan-Hua Liu、Fang Hu、Bing-Feng Shi

  DOI：10.1039/c6cc00822d

  日期：——

  The first example of Ni-catalyzed halogenation of (hetero)aryl C-H bonds with lithium halides (LiX, X=Br, I, Cl) using PIP as a removable directing group is reported. This protocol provides an...

  报道了使用PIP作为可去除的导向基团，镍与卤化锂（LiX，X ＝ Br，I，Cl）的Ni催化（杂）芳基CH键卤化的第一个例子。该协议提供了...
• 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.