ethyl 4-(4-(dimethylamino)phenyl)-3-oxobutanoate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 4-(4-(dimethylamino)phenyl)-3-oxobutanoate
• 英文别名: Ethyl 4-[4-(dimethylamino)phenyl]-3-oxobutanoate；ethyl 4-[4-(dimethylamino)phenyl]-3-oxobutanoate
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: MYNVZTXFXAWMAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 在 三叔丁基膦 、 三正丁基氟化锡 、 三乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 反应 27.25h， 生成 ethyl 4-(4-(dimethylamino)phenyl)-3-oxobutanoate
  参考文献：
  名称：

  Hauser–Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes

  摘要：

  gamma-Aryl-beta-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)(2)/t-Bu3P and stoichiometric amounts of Bu3SnF. The wide range of gamma-(hetero)aryl-beta-ketoesters that can be obtained illustrate the scope and limitations of this novel Hauser-Heck combination. gamma-Aryl-beta-ketoesters with a 1,3-dioxane acetal in the ortho position can easily be transformed into the hydroxy naphthoate in very good yield. Aqueous formic acid at 65 degrees C provides optimal conditions for this deprotective aromatization.

  DOI：

  10.1021/acs.orglett.5b02952

文献信息

• Hauser–Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes
  作者：Frederic Wagner、Klaus Harms、Ulrich Koert

  DOI：10.1021/acs.orglett.5b02952

  日期：2015.11.20

  gamma-Aryl-beta-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)(2)/t-Bu3P and stoichiometric amounts of Bu3SnF. The wide range of gamma-(hetero)aryl-beta-ketoesters that can be obtained illustrate the scope and limitations of this novel Hauser-Heck combination. gamma-Aryl-beta-ketoesters with a 1,3-dioxane acetal in the ortho position can easily be transformed into the hydroxy naphthoate in very good yield. Aqueous formic acid at 65 degrees C provides optimal conditions for this deprotective aromatization.