(E)-2-(1,2-diphenylvinyl)-N-methylbenzamide | 1315257-10-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(1,2-diphenylvinyl)-N-methylbenzamide
• CAS: 1315257-10-3
• 化学式: C₂₂H₁₉NO
• 分子量: 313.399
• InChiKey: SAHPTAYCISASHM-LTGZKZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(1,2-diphenylvinyl)-N-methylbenzamide 在 正丁基锂 、 苯基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Re/Mg Bimetallic Tandem Catalysis for [4+2] Annulation of Benzamides and Alkynes via C-H/N-H Functionalization

  摘要：

  A rhenium-magnesium cocatalyzed [4+2] annulation of benzamides and alkynes via C-H/N-H functionalization is described. The reaction features a divergent and high level of diastereoselectivities, which are readily switchable by subtle tuning of reaction conditions. Thus, a wide range of both cis- and trans-3,4-dihydroisoquinolinones is expediently synthesized in a highly atom-economical manner. Moreover, mechanistic studies unraveled a tandem mode of action between rhenium and magnesium in the catalytic cycles.

  DOI：

  10.1021/ja400020e
• 作为产物：
  描述：

  苯甲酸 在 氯化亚砜 、 五羰基溴铼(I) 、 三乙胺 、 苯基溴化镁 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (E)-2-(1,2-diphenylvinyl)-N-methylbenzamide
  参考文献：
  名称：

  Re/Mg Bimetallic Tandem Catalysis for [4+2] Annulation of Benzamides and Alkynes via C-H/N-H Functionalization

  摘要：

  A rhenium-magnesium cocatalyzed [4+2] annulation of benzamides and alkynes via C-H/N-H functionalization is described. The reaction features a divergent and high level of diastereoselectivities, which are readily switchable by subtle tuning of reaction conditions. Thus, a wide range of both cis- and trans-3,4-dihydroisoquinolinones is expediently synthesized in a highly atom-economical manner. Moreover, mechanistic studies unraveled a tandem mode of action between rhenium and magnesium in the catalytic cycles.

  DOI：

  10.1021/ja400020e

文献信息

• Ruthenium-Catalyzed Oxidative Annulation by Cleavage of CH/NH Bonds
  作者：Lutz Ackermann、Alexander V. Lygin、Nora Hofmann

  DOI：10.1002/anie.201101943

  日期：2011.7.4

  Bond activation in action: Unprecedented ruthenium‐catalyzed oxidative annulations of alkynes through cleavage of CH bonds set the stage for an efficient 1(2H)‐isoquinolone synthesis with ample scope (see scheme; tAm=tert‐amyl). Mechanistic studies provided strong evidence for a rate‐limiting CH bond metalation through carboxylate assistance.

  键活化在动作：以C裂解炔烃的前所未有的钌催化氧化annulations  H键设置阶段为一个有效的1（2 ħ）-isoquinolone合成了充足的范围（参见方案;吨AM =叔戊基）。机理研究为通过羧酸盐协助限速CH键金属化提供了有力证据。