(E)-1-Phenyl-3-(tri-n-butylstannyl)-2-propen-1-one | 142896-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-Phenyl-3-(tri-n-butylstannyl)-2-propen-1-one
• 英文别名: (E)-1-phenyl-3-(tributylstannyl)prop-2-en-1-one
• CAS: 142896-16-0
• 化学式: C₂₁H₃₄OSn
• 分子量: 421.21
• InChiKey: BFRAWPVJDXPLPB-UHFFFAOYSA-N

物化性质

• 沸点：
  424.6±51.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-Phenyl-3-(tri-n-butylstannyl)-2-propen-1-one 在 1,4-二氧六环 、 bis-triphenylphosphine-palladium(II) chloride 、 {Pd[C(CO₂Me)]4(Succ)}2(NBu₄)2 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (E)-1-Phenyl-4-(2-vinyl-oxazol-4-yl)-but-2-en-1-one
  参考文献：
  名称：

  4-Bromomethyl-2-chlorooxazole––a versatile oxazole cross-coupling unit for the synthesis of 2,4-disubstituted oxazoles

  摘要：

  The synthesis of the novel oxazole building block, 4-bromomethyl-2-chlorooxazole, and its palladium-catalysed cross-coupling reactions to make a range of 2,4-disubstituted oxazoles, is described. Selectivity for the 4-bromomethyl position is observed, with Stifle coupling effected in good to excellent yields, or Suzuki coupling in moderate yields, to provide a range of 4-substituted-2-chlorooxazoles. Subsequent coupling at the 2-chloro-position can be achieved through either Stille Or Suzuki reactions in excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.083
• 作为产物：
  描述：

  (E)-1-phenyl-3-(tributylstannyl)prop-2-en-1-ol 在 三甲基铝 、 间硝基苯甲醛 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以63%的产率得到(E)-1-Phenyl-3-(tri-n-butylstannyl)-2-propen-1-one
  参考文献：
  名称：

  脯氨酸催化环化反应合成萘并甲苯乙烯：在总合成吡咯啉中的应用

  摘要：

  描述了一种合成萘并苯乙烯的新方法。在这种方法中，顺序的Stille偶联和脯氨酸催化的环化过程用于4-溴代吲哚和β-三丁基锡烷基-α，β-不饱和酮的反应。该方法的实用性在从简单的2-异丙基苯酚进行的第一个全合成吡咯啉中得到了证明。

  DOI：

  10.1002/adsc.201500367

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.
• Proline-Catalyzed Cyclization Reaction for the Synthesis of Naphthostyrils: Application to the Total Synthesis of Prioline
  作者：Kyeong-Yong Park、Ha-Jeong Song、Jung-Nyoung Heo

  DOI：10.1002/adsc.201500367

  日期：2015.10.12

  A new method for the synthesis of naphthostyrils is described. In this method, a sequential Stille coupling and proline-catalyzed cyclization procedure is employed for the reaction of 4-bromooxindoles and β-tributylstannyl-α,β-unsaturated ketones. The utility of this methodology is demonstrated in the first total synthesis of prioline from a simple 2-isopropylphenol.

  描述了一种合成萘并苯乙烯的新方法。在这种方法中，顺序的Stille偶联和脯氨酸催化的环化过程用于4-溴代吲哚和β-三丁基锡烷基-α，β-不饱和酮的反应。该方法的实用性在从简单的2-异丙基苯酚进行的第一个全合成吡咯啉中得到了证明。
• 4-Bromomethyl-2-chlorooxazole––a versatile oxazole cross-coupling unit for the synthesis of 2,4-disubstituted oxazoles
  作者：Gail L. Young、Stephen A. Smith、Richard J.K. Taylor

  DOI：10.1016/j.tetlet.2004.03.083

  日期：2004.5

  The synthesis of the novel oxazole building block, 4-bromomethyl-2-chlorooxazole, and its palladium-catalysed cross-coupling reactions to make a range of 2,4-disubstituted oxazoles, is described. Selectivity for the 4-bromomethyl position is observed, with Stifle coupling effected in good to excellent yields, or Suzuki coupling in moderate yields, to provide a range of 4-substituted-2-chlorooxazoles. Subsequent coupling at the 2-chloro-position can be achieved through either Stille Or Suzuki reactions in excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.