N-(2-(pyridin-2-yl)propan-2-yl)benzamide-2-d1 | 1620194-08-2

• 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: N-(2-(pyridin-2-yl)propan-2-yl)benzamide-2-d1
• 英文别名: N-(2-(pyridin-2-yl)propan-2-yl)benzamide-2-d₁；N-(2-(pyridin-2-yl)propan-2-yl)benzamide-2-d
• CAS: 1620194-08-2
• 化学式: C₁₅H₁₆N₂O
• 分子量: 241.297
• InChiKey: SJZZWRMHAITYPT-BNEYPBHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-(pyridin-2-yl)propan-2-yl)benzamide-2-d1 在 copper (I) acetate 、 乙酸酐 、 lithium carbonate 、 silver nitrate 、 溶剂黄146 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Copper-/Silver-Mediated Arylation of C(sp²)–H Bonds with 2-Thiophenecarboxylic Acids

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b01560
• 作为产物：
  描述：

  邻碘溴苯 在 正丁基锂 、 氯化亚砜 、 异丙基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 N-(2-(pyridin-2-yl)propan-2-yl)benzamide-2-d1
  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

文献信息

• Copper(II)-Catalyzed Direct Sulfonylation of C(sp²)–H Bonds with Sodium Sulfinates
  作者：Wei-Hao Rao、Bing-Feng Shi

  DOI：10.1021/acs.orglett.5b01198

  日期：2015.6.5

  A copper-catalyzed direct sulfonylation of C(sp2)–H bonds with sodium sulfinates using a removable directing group is described. This reaction tolerates a wide range of functional groups, providing an efficient protocol for the synthesis of diverse aryl sulfones. Moreover, a series of 2,6-disubstituted benzamides could be synthesized via sequential C–H functionalization.

  描述了使用可去除的导向基团与亚磺酸钠的铜催化的C（sp 2）-H键的直接磺酰化。该反应可耐受各种官能团，为合成各种芳基砜提供了有效的方法。此外，可以通过连续的C–H官能化合成一系列2,6-二取代的苯甲酰胺。
• Copper/Silver-Mediated Direct<i>ortho</i>-Ethynylation of Unactivated (Hetero)aryl CH Bonds with Terminal Alkyne
  作者：Yue-Jin Liu、Yan-Hua Liu、Xue-Song Yin、Wen-Jia Gu、Bing-Feng Shi

  DOI：10.1002/chem.201405594

  日期：2015.1.2

  directing group and features broad substrate scope, high functional‐group tolerance, and compatibility with a wide range of heterocycles, providing an efficient synthesis of aryl alkynes. This procedure highlights the potential of copper catalysts to promote unique, synthetically enabling CH functionalization reactions that lie outside of the current scope of precious metal catalysis.

  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。
• 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。
• Nickel-Catalyzed <i>Ortho-</i>Arylation of Unactivated (Hetero)aryl C–H Bonds with Arylsilanes Using a Removable Auxiliary
  作者：Sheng Zhao、Bin Liu、Bei-Bei Zhan、Wei-Dong Zhang、Bing-Feng Shi

  DOI：10.1021/acs.orglett.6b02236

  日期：2016.9.16

  Ni(II)-catalyzed ortho-arylation of aromatic and heteroaromatic carboxamides with triethoxy(aryl)silanes assisted by a removable bidentate auxiliary is reported. This transformation features a broad substrate scope, good functional group tolerance, and compatibility with heterocyclic substrates. Compared to the well-established Ni(II)-catalyzed C–H arylation with ArX or aryliodonium salts via oxidative

  据报道，在可移动的二齿助剂的辅助下，Ni（II）催化的芳族和杂芳族羧酰胺与三乙氧基（芳基）硅烷的邻位芳基化。这种转变具有广泛的底物范围，良好的官能团耐受性以及与杂环底物的相容性。与已建立的Ni（II）催化的ArX或芳基碘鎓盐通过氧化加成反应的C–H芳基化反应相比，该反应是通过氟化物促进的重金属化反应进行的。
• 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。