N-(3-phenyl-2H-chromen-4-yl)acetamide | 1174743-82-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: N-(3-phenyl-2H-chromen-4-yl)acetamide
• CAS: 1174743-82-8
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: PDRQTCIDKFCAEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯基三甲氧基硅烷 、 N-(2H-chromen-4-yl)acetamide 在 palladium diacetate 、 silver fluoride 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以73%的产率得到N-(3-phenyl-2H-chromen-4-yl)acetamide
  参考文献：
  名称：

  sp2 C对钯催化的环酰胺与芳基硅烷的直接芳基化作用？H激活

  摘要：

  它确实进入！氟化物辅助的环戊酰胺与三烷氧基芳基硅烷的直接交叉偶联，通过钯催化的CH活化作用，可产生多种酰胺，收率高达95％。

  DOI：

  10.1002/anie.200901884

文献信息

• Palladium-Catalyzed Direct Arylation of Cyclic Enamides with Aryl Silanes by sp2 CH Activation
  作者：Hai Zhou、Yun-He Xu、Wan-Jun Chung、Teck-Peng Loh

  DOI：10.1002/anie.200901884

  日期：——

  It does get in! A fluoride‐assisted direct cross‐coupling of cyclic enamides with trialkoxy aryl silanes by a palladium‐catalyzed CH activation leads to a wide range of enamides in yields of up to 95 %.

  它确实进入！氟化物辅助的环戊酰胺与三烷氧基芳基硅烷的直接交叉偶联，通过钯催化的CH活化作用，可产生多种酰胺，收率高达95％。
• Direct arylation of cyclic enamides via Pd(ii)-catalyzed C–H activation
  作者：Hai Zhou、Wan-Jun Chung、Yun-He Xu、Teck-Peng Loh

  DOI：10.1039/b903151k

  日期：——

  A new direct coupling of cyclic enamides with aryl boronic acids viaPd(II)-catalyzed C–H functionalization has been achieved with good yields (up to 90%).

  通过钯（II）催化的 CâH 功能化，实现了环烯丙基酰胺与芳基硼酸的一种新的直接偶联，并取得了良好的收率（高达 90%）。
• Copper(I) Bromide Catalyzed Arylation of Cyclic Enamides and Naphthyl-1-acetamides Using Diaryliodonium Salts
  作者：Muthuraj Prakash、Subramaniam Muthusamy、Venkitasamy Kesavan

  DOI：10.1021/jo501162s

  日期：2014.9.5

  Copper(I) bromide catalyzed direct C-H arylation of cyclic enamides was achieved using diaryliodonium salts in the absence of base/additive at ambient temperature with high yields. A biologically active dihydro[a]benzocarbazole scaffold was synthesized using the established protocol. The scope of the current methodology was further extended for the synthesis of C4-, C7-aryl-substituted 1-naphthyl acetamides in good yields.
• Catalytic C–H Activation/C–C Coupling Reaction: DFT Studies on the Mechanism, Solvent Effect, and Role of Additive
  作者：Lei Zhang、De-Cai Fang

  DOI：10.1021/jo302567s

  日期：2013.3.15

  A series of density functional theory (DFT) experiments, employing the B3LYP+IDSCRF/BS1 and B3LYP +IDSCRF/DZVP methods, have been carried out for the Pd(OAc)(2)-catalyzed enamide-siloxane C-H activation/C-C coupling reactions. The results reveal that there are four processes, namely C-H activation, transmetalation (TM), reductive elimination (RE), and separation of product (SP) and recycling of catalyst (RC), each of which is consist of different steps. In order to fully understand the origin of regiospecific C-H activation/C-C coupling on the alicyclic ring experimentally observed, the conformational preference, kinetic aspects, and relative stabilities of the competitive products have been explored. In addition, the roles of additive silver salt AgF and solvent dioxane have also been addressed, providing valuable details upon which to rationally optimize experimental conditions.