N-(α-methylbenzyl)-3,4-(methylenedioxy)aniline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-(α-methylbenzyl)-3,4-(methylenedioxy)aniline
• 英文别名: benzo[1,3]dioxol-5-yl-(1-phenyl-ethyl)-amine；N-(1-phenylethyl)-1,3-benzodioxol-5-amine
• 化学式: C₁₅H₁₅NO₂
• mdl: MFCD11147775
• 分子量: 241.29
• InChiKey: ANVNAFWMENAOGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-phenylethanone oxime 在 噻吩-2-甲酸亚铜(I) sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N-(α-methylbenzyl)-3,4-(methylenedioxy)aniline
  参考文献：
  名称：

  N-Substituted Imines by the Copper-Catalyzed N-Imination of Boronic Acids and Organostannanes with O-Acyl Ketoximes

  摘要：

  Catalytic quantities of copper(I) or copper(II) sources catalyze the N-imination of boronic acids and organostannanes through reaction with oxime O-carboxylates under nonbasic conditions. This method tolerates various functional groups and takes place efficiently using aryl, heteroaryl, and alkenyl boronic acids and stannanes.

  DOI：

  10.1021/ol070561w

文献信息

• Synthesis of Bulky and Electron-Rich MOP-type Ligands and Their Applications in Palladium-Catalyzed C−N Bond Formation
  作者：Xiaomin Xie、Tony Y. Zhang、Zhaoguo Zhang

  DOI：10.1021/jo060945k

  日期：2006.8.1

  A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands ( 6a-c and 8a-c) have been prepared conveniently by a lithium-initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution. Application of these phosphine ligands in palladium-catalyzed C-N bond forming reactions revealed the crucial roles of the steric bulk of the substituents on the phosphorus atom governing the catalytic activity. Specifically, 2-di-tert-butylphosphino-2'-isopropoxy-1, 1'-binaphthyl ( 8b) proved to be the most effective for the aminations of aryl halides with primary amines, while the less bulky 2-dicyclohexyl-2'-methoxy-1,1'-binaphthyl ( 6a) was more effective for the aminations with secondary amines. The steric and electronic effects of the ligands were analyzed to account for these observations.
• N-Substituted Imines by the Copper-Catalyzed <i>N</i>-Imination of Boronic Acids and Organostannanes with <i>O</i>-Acyl Ketoximes
  作者：Songbai Liu、Ying Yu、Lanny S. Liebeskind

  DOI：10.1021/ol070561w

  日期：2007.5.1

  Catalytic quantities of copper(I) or copper(II) sources catalyze the N-imination of boronic acids and organostannanes through reaction with oxime O-carboxylates under nonbasic conditions. This method tolerates various functional groups and takes place efficiently using aryl, heteroaryl, and alkenyl boronic acids and stannanes.