(E)-1-(3-Furanyl)-3-(tri-n-butylstannyl)-2-propen-1-one | 142896-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(3-Furanyl)-3-(tri-n-butylstannyl)-2-propen-1-one
• CAS: 142896-17-1
• 化学式: C₁₉H₃₂O₂Sn
• 分子量: 411.172
• InChiKey: DUYKFRQJMMFWSF-UHFFFAOYSA-N

物化性质

• 沸点：
  403.7±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-Furanyl)-3-(tri-n-butylstannyl)-2-propen-1-one 、 乙酰氯 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 以100%的产率得到1-(呋喃-3-基)戊烷-1,4-二酮
  参考文献：
  名称：

  Palladium-Catalyzed Reductive Coupling of Acid Chlorides with .beta.-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects

  摘要：

  The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or beta-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate. The double bond conjugated with a single carbonyl group was not significantly reduced. The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine. By performing the reaction at lower temperatures, alpha,beta-unsaturated 1,4-diketones can also be prepared. The reduction of the intermediate alpha,beta-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu(3)SnCl, followed by hydrolysis of the intermediate palladium enolate.

  DOI：

  10.1021/jo00094a032

文献信息

• Synthesis of 1,4-diketones by palladium-catalyzed reductive coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or .beta.-stannyl enones
  作者：Marta Perez、Ana M. Castano、Antonio M. Echavarren

  DOI：10.1021/jo00045a002

  日期：1992.9

  The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or beta-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl derivative by a palladium hydride derived from n-Bu3SnCl.
• Palladium-Catalyzed Reductive Coupling of Acid Chlorides with .beta.-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects
  作者：Antonio M. Echavarren、Marta Perez、Ana M. Castano、Juan M. Cuerva

  DOI：10.1021/jo00094a032

  日期：1994.7

  The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or beta-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate. The double bond conjugated with a single carbonyl group was not significantly reduced. The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine. By performing the reaction at lower temperatures, alpha,beta-unsaturated 1,4-diketones can also be prepared. The reduction of the intermediate alpha,beta-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu(3)SnCl, followed by hydrolysis of the intermediate palladium enolate.