N,N-dimethyl-4-(1-Methyl-2-propen-1-yl)benzenamine | 1092390-63-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-4-(1-Methyl-2-propen-1-yl)benzenamine
• 英文别名: 4-but-3-en-2-yl-N,N-dimethylaniline
• CAS: 1092390-63-0
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: PQPWBZWEVMNBHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-巴豆氯 、 4-溴-N,N-二甲基苯胺 在 magnesium 、 copper(II) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 生成 4-but-2-enyl-N,N-dimethylaniline 、 N,N-dimethyl-4-(1-Methyl-2-propen-1-yl)benzenamine
  参考文献：
  名称：

  重新审视格氏试剂的烯丙基偶联：纳米铜催化的一锅α-选择性芳基-烯丙基偶联

  摘要：

  过渡金属催化的有机金属化合物烯丙基化是形成 CC 键最有价值的方法之一。 1-9 由于它们易于制备、高反应性和有趣的...

  DOI：

  10.1080/00304948.2017.1374104

文献信息

• Cross-Coupling of Aromatic Bromides with Allylic Silanolate Salts
  作者：Scott E. Denmark、Nathan S. Werner

  DOI：10.1021/ja805951j

  日期：2008.12.3

  The sodium salts of allyldimethylsilanol and 2-butenyldimethylsilanol undergo palladium-catalyzed cross-coupling with a wide variety of aryl bromides to afford allylated and crotylated arenes. The coupling of both silanolates required extensive optimization to deliver the expected products in high yields. The reaction of the allyldimethylsilanolate takes place at 85 degrees C in 1,2-dimethoxyethane with allylpalladium chloride dimer (2.5 mol %) to afford 73-95% yields of the allylation products. Both electron-rich and sterically hindered bromides reacted smoothly, whereas electron-poor bromides cross-coupled in poor yield because of a secondary isomerization to the 1-propenyl isomer (and subsequent polymerization). The 2-butenyldimethylsilanolate (E/Z, 80:20) required additional optimization to maximize the formation of the branched (gamma-substitution) product. A remarkable influence of added alkenes (dibenzylideneacetone and norbornadiene) led to good selectivities for electron-rich and electron-poor bromides in 40-83% yields. However, bromides containing coordinating groups (particularly in the ortho position) gave lower, and in one case even reversed, selectivity. Configurationally homogeneous (E)-silanolates gave slightly higher gamma-selectivity than the pure (2)-silanolates. A unified mechanistic picture involving initial gamma-transmetalation followed by direct reductive elimination or sigma-pi isomerization can rationalize all of the observed trends.
• Revisiting Allylic Coupling of Grignard Reagents: Nano Copper Catalyzed One-Pot α-Selective Aryl-Allyl Coupling
  作者：Melike Kalkan、Ender Erdik、Özgen Ömür Pekel

  DOI：10.1080/00304948.2017.1374104

  日期：2017.9.3

  Transition metal catalyzed allylation of organometallic compounds is one of the most valuable methodologies for the formation of C-C bonds.1-9 Due to their easy preparation, high reactivity and fun...

  过渡金属催化的有机金属化合物烯丙基化是形成 CC 键最有价值的方法之一。 1-9 由于它们易于制备、高反应性和有趣的...