2-[1-(3-fluorophenyl)-2-methylpropylidene]malonic acid diethyl ester | 778580-45-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[1-(3-fluorophenyl)-2-methylpropylidene]malonic acid diethyl ester
• 英文别名: Diethyl 2-[1-(3-fluorophenyl)-2-methylpropylidene]propanedioate
• CAS: 778580-45-3
• 化学式: C₁₇H₂₁FO₄
• 分子量: 308.35
• InChiKey: SLRLPLHQNNJELS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1-(3-fluorophenyl)-2-methylpropylidene]malonic acid diethyl ester 在 PPA 作用下， 反应 1.5h， 以50%的产率得到Ethyl 5-fluoro-1-oxo-3-propan-2-ylindene-2-carboxylate
  参考文献：
  名称：

  Efficient Palladium-Catalyzed Cross-Coupling of β-Chloroalkylidene/arylidene Malonates Using Microwave Chemistry

  摘要：

  A general method for the synthesis of beta-aryl/alkylarylidene malonates is reported. The key step involves the coupling of an arylboronic acid to a beta-chloroalkyl/arylidene malonate, in the presence of K2CO3 and 1 mol % of the air-stable palladium catalyst (POPd) under microwave irradiation, to afford beta-aryl/alkylarylidene malonates in good yields. The combination of mild reaction conditions, air stable catalyst, microwave-enhanced chemistry, and high levels of functional group compatibility make this an attractive synthetic approach to this class of compounds.

  DOI：

  10.1021/jo049132r
• 作为产物：
  描述：

  异丁酰基丙二酸二乙酯 在 三正丁胺 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-[1-(3-fluorophenyl)-2-methylpropylidene]malonic acid diethyl ester
  参考文献：
  名称：

  Efficient Palladium-Catalyzed Cross-Coupling of β-Chloroalkylidene/arylidene Malonates Using Microwave Chemistry

  摘要：

  A general method for the synthesis of beta-aryl/alkylarylidene malonates is reported. The key step involves the coupling of an arylboronic acid to a beta-chloroalkyl/arylidene malonate, in the presence of K2CO3 and 1 mol % of the air-stable palladium catalyst (POPd) under microwave irradiation, to afford beta-aryl/alkylarylidene malonates in good yields. The combination of mild reaction conditions, air stable catalyst, microwave-enhanced chemistry, and high levels of functional group compatibility make this an attractive synthetic approach to this class of compounds.

  DOI：

  10.1021/jo049132r

文献信息

• Efficient Palladium-Catalyzed Cross-Coupling of β-Chloroalkylidene/arylidene Malonates Using Microwave Chemistry
  作者：Rajamohan R. Poondra、Peter M. Fischer、Nicholas J. Turner

  DOI：10.1021/jo049132r

  日期：2004.10.1

  A general method for the synthesis of beta-aryl/alkylarylidene malonates is reported. The key step involves the coupling of an arylboronic acid to a beta-chloroalkyl/arylidene malonate, in the presence of K2CO3 and 1 mol % of the air-stable palladium catalyst (POPd) under microwave irradiation, to afford beta-aryl/alkylarylidene malonates in good yields. The combination of mild reaction conditions, air stable catalyst, microwave-enhanced chemistry, and high levels of functional group compatibility make this an attractive synthetic approach to this class of compounds.